“Chemistry is applied theology.”
TIMOTHY LEARY POLITICS OF ECSTASY (1982, 271*)
“Life is the convergence of mind and matter.”
GALAN O. SEID (11/1996)
“It is in fact a miracle, a secret of the world in the full light of the day, to experience how the prosaic alcoholic matter in a glass of wine dispels sadness and worries, how ether fumes or chloroform can cause a person to temporarily lose consciousness, how morphine can dull even the most severe pain, and how Veronal, Luminal, and other preparations help a sleepless person to find slumber. No philosopher, no medical doctor, and no chemist has ever solved these riddles, and it is not likely that they will be solved in the future either. Today, and in the centuries to come, we will have to be satisfied with collecting the most comprehensive, certain, and reliable knowledge possible that stems from experience with these substances. And indeed, man will investigate ever more precisely how the countless natural and synthetic substances affect human beings, which concentrations and methods of administration are the most useful, which aftereffects appear, and how such factors as age, physical constitution, race, sex, occupation, and state of health have to be taken into consideration, etc. We should not look down upon such experience-based knowledge, for it leads to healing success or at least to the elimination of the anguishing symptoms of disease—and for a compassionate human being, this is certainly a matter of greater importance than the most wonderful theory about the physical and mental processes.”
HERMANN RÖMPP CHEMISCHE ZAUBERTRÄNKE [CHEMICAL POTIONS] (1950, 7*)
Over the past two centuries, pharmaceutical and pharmacological research has recognized that it is not the plants themselves that produce the particular effects but the principles or active constituents that reside within them. But what is an active constituent? Active constituents are chemically uniform substances (molecules) that can be extracted from plants with the help of solvents and which cause an effect when ingested. They either occur in the form of oily substances (bases) or can be crystallized out as salts.
Jonathan Ott, a chemist of natural substances, once discussed the effects of plants and plant spirits with a shaman in the Amazon. Ott used the metaphor that modern chemistry had discovered that the spirit of a plant exists in the form of a crystal. This picture made sense to the traditional shaman, for whom crystals are gateways to another reality, a kind of crystallized consciousness.
However, experiences with plants and their active constituents have made it evident that the effects of the molecule or the so-called main active constituent are not necessarily identical to the effects of the plant that contains the substance (cf. Storl 1996a*, 1996b*). The pharmacological explanation for this fact is that most plants contain a mixture of active constituents, and it is the synergy among these that is responsible for the characteristic effects of that plant. A plant usually induces a broader spectrum of effects than is produced by its isolated components. In other words, a pure constituent is more specific in its action.
There are people who believe that only natural substances are capable of producing good or tolerable effects, and that synthesizing those same molecules alters their pharmacological behavior so they will not work as well as the natural molecules. However, neither the chemical nor the pharmacological perspectives provide support for this notion.
Many people believe that “new” molecules that have been artificially produced by chemists, such as LSD, MDMA, and ketamine, are not as good as compounds found in the natural world. It would be wise to remember, however, that a chemist is not really able to create artificial molecules. All he or she can do is to make use of the properties of substances so that a specific molecule can form. Moreover, simply because a molecule that was first produced in a laboratory was at the time unknown in nature does not mean that the molecule does not occur in some plant that has not yet been discovered or studied. For example, N,N-DMT was first synthesized in a laboratory and described as an artificial molecule. Later, it was discovered that this same molecule occurs naturally in plants, animals, and even humans. Valium (= diazepam) is regarded as the artificial drug par excellence and feared as an addictive poison. Yet this substance, which was initially synthesized in a laboratory, has since been found to occur naturally in potatoes and cereal grains. It is quite likely that LSD, MDMA, and ketamine will soon be detected in psychoactive plants as well. Chemists are merely transformers of matter; they are not gods. All they do is apply a “divine law.”
Active Plant Constituents and Neurotransmitters
Neurotransmitters, also known as transmitters or chemical messengers, are substances that are released at presynaptic nerve endings (or axon terminals), cross the synaptic cleft, and induce changes at the postsynaptic membrane, i.e., the next neuron (Black 1993*; Snyder 1989*; Spitzer 1996*). In other words, they are a chemical message that is sent out at the end of one neuron and read by the next. The first neurotransmitters to be discovered were the endorphins, substances that are produced in the body itself (= endogenous) and act within the nervous system in the same manner as morphine and other related opiates. We now know that the purposeful activation of particular neurotransmitters can induce psychoactive experiences or altered states of consciousness that resemble or even correspond to those induced by active plant constituents:
Man is his own drug producer; he simply needs to relearn how to stimulate his endogenous drugs as he needs and desires. . . . Until now, the deliberate and targeted stimulation of endogenous drugs has been an unexplored territory in the field of biomedicine. But ritual healing cults and archaic methods of healing (shamanism, the voodoo cult, healing dances, yoga, meditation) include numerous elements for stimulating the production of endogenous drugs, although the participants of course are typically unaware of the biochemical background. (Zehentbauer 1992*)
In other words, the perspective offered by neurochemistry tells us that an alteration in a person’s state of consciousness is always triggered by some type of drug, whether this is a neuro-transmitter produced by one’s own body or one that comes from outside in the form of an active plant constituent: “Endogenous drugs can produce effects similar to those produced by exogenous ‘miracle drugs’ ” (Zehentbauer 1992, 113*).
Most shamans, however, prefer to use “plant spirits” to produce the states they desire, for the ingestion of a psychoactive substance is the most reliable method for achieving a desired altered state of consciousness. Mushrooms, for example, are always dependable. Shamans have no time for techniques that work only on occasion.
Research into migraines has shed some light onto the relationship between neurotransmitters and hallucinations or visions. Migraines are frequently accompanied by hallucinations (phosphenes, abstract patterns, strange shapes) whose form and content are often indistinguishable from the hallucinations or perceptual changes induced by the active constituents of plants. The only real difference is that migraines are very painful, whereas the states of consciousness produced by plant constituents are usually euphoric and pleasant in nature.
Analogies between Exogenous and Endogenous Neurotransmitters
(from Perrine 1996*; Snyder 1989*; Zehentbauer 1992*; supplemented)
“Molecules are alive!—I believe that chemical compounds can teach us just as well as plants.”
DR. ALEXANDER T. SHULGIN ASK DR. SHULGIN ONLINE, DRUG INFORMATION WEB SITE OF THE CENTER FOR COGNITIVE LIBERTY AND ETHICS
There is evidence that all natural neuro-transmitters may show significant changes during an attack of migraine. . . . We see changes in adrenalin, nor-adrenalin, acetylcholine, histamine; and, often prominently, in 5-hydroxy-tryptamine (or serotonin). (Sacks 1985, 193*)
All of these neurotransmitters have their analogs in psychoactive plants: cocaine, scopola-mine/atropine, mescaline, histamine, muscimol/ ibotenic acid, morphine, psilocybin, and psilocin. This means that the ability to produce hallucinations and visions is a normal property of our nervous system. It apparently makes no difference whether these states are caused by endogenous neurotransmitters or by exogenous neurotransmitters, i.e., active plant constituents.
Several neurotransmitters that are vitally important in the human nervous system also occur in plants. Acetylcholine can be found in the scarlet runner bean (Phaseolus coccineus L. [syn. Phaseolus multiflorus Lam.]), in various mimosas (Mimosa spp.), in Albizia julibrissin Durazz., and in peas (Pisum sativum L.), all members of the Family Leguminosae. Serotonin occurs in numerous plants and fungi (Panaeolus subbalteatus). Bananas (Musa x sapientum) and the orange root (Hydrastis canadensis L.; Ranunculaceae) contain norepinephrine.
Why plants produce and contain human neurotransmitters is unknown to the scientific community (Applewhite 1973*). For the shaman, on the other hand, the answer is clear: The active constituent, the plant spirit, is a messenger in the neural network of nature. Every human, like every plant and animal, is one of infinitely many neurons in the nervous system of Gaia. The active constituents found in plants are the neurotransmitters, the communication system, of living nature.
Some psychoactive constituents can be found in humans as well as in other animals and plants. Morphine, for example, occurs in cow’s milk, in the human brain, and in poppy juice. Bufotenine has been detected in human urine, in the secretions of certain toads, and in many plants and fungi. In those cases in which an active constituent of a plant is not identical to an endogenous substance, it is analogous. In other words, the active constituent behaves within the human nervous system in the same way as the endogenous neurotransmitter, occupying the same specific receptors at the neural terminals. This is the only reason that plant active constituents can do what they do. Substances that are not identical or analogous to neurotransmitters appear to be unable to induce any psychoactive effects (laughing gas is an exception491). Alcohol appears to affect neuro-transmission in a variety of ways.
For the shaman, it is of no importance whether one of his plant spirits affects serotonin transmission, the adrenergic system, or some other aspect of the nervous system. He can achieve the same effects—trance, ecstasy, and journeying to another world—with pharmacologically quite different substances. Adolf Dittrich (1996*) came to a similar conclusion when he was developing a phenomenology of altered states of consciousness based upon his experimental and empirical research. He found that states with very different etiologies can have the same content.
Neurotransmission provides but one perspective for explaining the occurrence of altered states of consciousness. And all pharmacological explanations are ultimately nothing more than models for understanding the mysterious play of our consciousness.
The Active Plant Constituents from A to Z
The following section discusses the most important active constituents and types of substances found in psychoactive plants. Particular attention is given to those substances that have acquired a significance as a psychoactive drug in a cultural setting or have played a key role in the history of pharmacology. This section will also enable the reader to locate plants that contain a particular agent or substances of a particular type (see the various tables).
The names of the substances are spelled as they are most commonly found in the popular literature and consequently will not always conform to the spelling accepted in the chemical literature. Indeed, inconsistencies in both spelling and nomenclature are not uncommon in this field.
A primary focus of this section is on the cultural significance of the different active plant constituents. For other information, the reader is referred to the chemical, pharmacological, and neurochemical literature (e.g., Du Quesne and Reeves 1982*; Ebel and Roth 1987*; Hagers Handbuch der pharmazeutischen Praxis [Hagers Handbook of Pharmaceutical Practice]; Hunnius 1975*; Inaba and Cohen 1993*; Lenson 1995*; Lin and Glennon 1994*; Ott 1993*; Perrine 1996*; Römpp Chemielexikon [Roempp’s Dictionary of Chemistry]; Roth et al. 1994*; Seymour and Smith 1987*; Shulgin 1992*; and Wagner 1985*).
The groups or types of substances discussed below include: β-carbolines, β-phenethylamines, coumarins, diterpenes, ergot alkaloids, essential oils, indole alkaloids, opium alkaloids, tropane alkaloids, and withanolides. The following individual substances are treated in their own sections: atropine, bufotenine, caffeine, cocaine, codeine, cytisine, diazepam, ephedrine, 5-MeO-DMT, harmaline and harmine, ibogaine, ibotenic acid, mescaline, morphine, muscimol, nicotine, N,N-DMT, papaverine, psilocybin/psilocin, salvinorin A, scopolamine, scopoletin, strychnine, THC, and yohimbine.
The flowers of the linden tree contain sedative substances that bind to benzodiazepine receptors. (Woodcut from Fuchs, Läebliche abbildung und contrafaytung aller kreüter, 1545)
The milky sap that oozes from scored poppy capsules thickens into raw opium when exposed to air. In 1805, German pharmacist Friedrich Sertürner became the first person in the history of pharmacology to extract a pure chemical constituent from opium. He named the alkaloid morphium (= morphine) after Morpheus, the ancient god of sleep.
Atropin, atropina, atropinum, atropium, DL-hyoscyamine, d,l-hyoscyaminum, DL-tropyltropate, (±)-hyoscyamine, 3α(1αH,5αH)-tropanyl-(RS)-tropate, tropintropate
Empirical formula: C17H23NO3
Substance type: tropane alkaloid
Atropine was first isolated from the deadly night-shade (Atropa belladonna) in 1820 by Rudolph Brandes, who named the compound after the genus. Atropine is found in many plants of the Nightshade Family (including the genera Atropa, Brugmansia, Datura, Hyoscyamus, Latua, Mandragora). Atropine is chemically related to cocaine (Willstaedter 1889). It also is closely related to scopolamine and hyoscyamine. Hyoscyamine, which is present in many living plants, quickly racemizes into atropine when the raw drugs are dried or stored.
A therapeutic dosage is usually considered to be 1 mg. It is possible that 10 mg is lethal for children and babies, but not for adults:
Relatively high doses (10 mg atropine sulfate and above) have a stimulating effect on the central nervous system, affecting especially the cerebrum, diencephalon, and medulla oblongata. The arousal is followed by an anesthesia-like paralysis that can lead to coma and a fatal respiratory paralysis. (Roth et al. 1994, 945*)
The lethal oral dosage for an adult is approximately 100 mg (Roth et al. 1994, 765*).
The range of atropine’s effects includes psychomotor agitation, excitation, constant repetition of a particular activity pattern, a need to talk, euphoria, crying spells, confused speech, hallucinations, spasms, delirium, flushing of the skin, drying of the mucous membranes, coma, unconsciousness, and heart arrhythmia (Roth et al. 1994, 945*). One particularly characteristic effect is a long-lasting dilation of the pupils (mydriasis). It is because of this effect that atropine has long been used in ophthalmology (Jürgens 1930). Atropine is also utilized as a component in certain anesthetics (in combination with morphine). Injections of atropine are often administered prior to surgery so that the mucous membranes will remain dry during the procedure and the patient will not choke on his or her own saliva. Atropine has also been used to treat asthma (Terray 1909).
When it is given orally, the typical effects of atropine (dry mouth, pupillary dilation, increased pulse rate) manifest about twice as strong as compared to intramuscular injection (Mirakhur 1978). Some of the atropine is excreted in the urine unchanged (Roth et al. 1994, 945*).
Atropine is an important antidote in cases of poisoning (overdoses) caused by the fungal toxin muscarine (cf. Inocybe spp.), Digitalis purpurea, hydrogen cyanide, opium (cf. Papaver somniferum), and morphine (Römpp 1995, 298*). Overdoses of atropine can be successfully treated with morphine.
Because of its unpleasant side effects (dryness of the mouth, difficulties in swallowing, disturbances in vision, confusion), atropine as a pure alkaloid has never acquired any cultural significance as a psychoactive substance. However, the medical literature does contain a few reports of “atropine addiction” (Flincker 1932).
Commercial Forms and Regulations
Atropine is available both as a pure substance and as atropine sulfate. Although regulated as a dangerous substance, it can be obtained with a prescription and is not included on any list of “narcotic drugs” (Koerner 1994, 1573*).
The deadly nightshade (Atropa belladonna L.). (From Giftgewächse [Poisonous Plants], 1875)
See also the entries for Atropa belladonna, Latua pubiflora, cocaine, and tropane alkaloids.
Brandes, Rudolph. 1920. Über das Atropium, ein neues Alkaloid in den Blättern der Belladonna (Atropa belladonna L.). Journal für Chemie und Physik 28:9–31.
Flincker, R. 1932. Über Abstinenz-Erscheinungen bei Atropin. Münchner Medizinische Wochenschrift 17:540–41.
Jürgensen, E. 1930. Atropin im Wandel der Zeiten. Ärtztliche Rundschau (Munich; 1930): 5–8.
Ketchum, J. S., F. R. Sidell, E. B. Crowell, G. K. Aghajanian, and A. H. Hayes. 1973. Atropine, scopolamine and ditran: Comparative pharmacology and antagonists in man. Psychopharmacology 28:121–45.
Mirakhur, R. K. 1978. Comparative study of the effects of oral and i.m. atropine and hyoscine in volunteers. British Journal of Anaesthesia 50 (6): 591–98.
Terray, Paul von. 1909. Über Asthma Bronchiale und dessen Behandlung mit Atropin. Medizinische Klinik 1 (5): 79–83.
Willstätter, R. 1898. Über die Constitution der Spaltungsprodukte von Atropin und Cocain. Berichte der Deutschen Chemischen Gesellschaft 31:1534–53.
Beta-carbolines, β-carbolines, βCs
β-carbolines are derived from the actual β-carbo-line (norharmane). They belong to the group of indole alkaloids and are closely related to tryptamines. They consist of an indole skeleton and various side chains.
The psychoactive effects of β-carbolines are due primarily to the harmala alkaloids harmaline, harmine, harmalol, harmane (1-methyl-β-carbo-line), and norharmane (β-carboline) (Naranjo 1967). The simpler (-carboline) alkaloids occur in numerous plants (Allen and Holmstedt 1980).
Many plants that produce psychoactive effects or are utilized for psychoactive purposes contain β-carbolines (including Acacia spp., Arundo donax, Banisteriopsis caapi, Banisteriopsis spp., Mucuna pruriens, Papaver spp., Passiflora spp., Peganum harmala, Phalaris arundinacea, Phalaris spp., Psychotria spp., Strychnos spp., Virola spp., Tribulus terrestris, and Amanita muscaria). These compounds are also present in tobacco smoke (cf. Nicotiana tabacum) and in many plants that are used traditionally to make ayahuasca or are now used as ayahuasca analogs (Schultes 1982).
Many β-carbolines occur as endogenous substances in animals and in humans, where they serve important functions in the nervous system (Bringmann et al. 1991). They appear to influence both moods and dreaming. It is likely that norharmane (β-carboline) occupies a specific β-carboline receptor. Harmane is the endogenous MAO (monoamine oxidase) inhibitor, suppressing MAO-A (Rommelspacher et al. 1991). This allows the endogenous N,N-DMT to persist for a longer duration and trigger visionary perceptions that manifest either as spontaneous visions during the waking state or as dreams while sleeping (Callaway et al. 1995).
The harmala alkaloids harmaline, harmine, harmane, and tetrahydroharmane are all MAO inhibitors that inhibit primarily MAO-A (Buckholtz and Bogan 1977; McIsaac and Estévez 1966).
In the presence of certain foods, MAO inhibitors are considered to be dangerous or even very dangerous. Tyramine, which is found in such foods as aged cheese, is especially hazardous. If it is not broken down by MAO, it can cause severe toxic effects to an organism. More-recent studies, however, have shown that the dangers have been greatly exaggerated in both the literature and “on the street.” Moreover, the amount of tyramine contained in most “dangerous” foods tends to be rather low (Berlin and Lecrubier 1996).
Allen, J. R. F., and Bo Holmstedt. 1980. The simple β-carboline alkaloids. Phytochemistry 19:1573–82.
Berlin, Ivan, and Yves Lecrubier. 1996. Food and drug interactions with monoamine oxidase inhibitors: How safe are the newer agents? CNS Drugs 5 (6): 403–13.
Bringmann, Gerhard, Doris Feineis, Heike Friedrich, and Anette Hille. 1991. Endogenous alkaloids in man—synthesis, analytics, in vivo identification, and medicinal importance. Planta Medica 57 suppl. (1): 73–84.
Buckholtz, N. S., and W. O. Bogan. 1977. Monoaminooxydase inhibition in brain and liver produced by β-carbolines: Structure-activity relationships and substrate specificity. Biochemical Pharmacology 26:1991–96.
Callaway, James C., M. M. Airaksinen, and J. Gynther. 1995. Endogenous β-carbolines and other indole alkaloids in mammals. Integration 5:19–33. (Includes a very comprehensive bibliography.)
McIsaac, W. M., and V. Estévez. 1966. Structure-activity relationship of β-carbolines monoamine oxidase inhibitors. Biochemical Pharmacology 15:1625–27.
Naranjo, Claudio. 1967. Psychotropic properties of the harmala alkaloids. In Ethnopharmacologic search for psychoactive drugs, ed. D. H. Efron, 385–91. Washington, D.C.: U.S. Department of Health, Education, and Welfare.
Rommelspacher, Hans, Torsten May, and Rudi Susilo. 1991. β-carbolines and tetrahydroisoquinolines: Detection and function in mammals. Planta Medica 57 suppl. (1): 93 ff.
Schultes, Richard Evans. 1982. The beta-carboline hallucinogens of South America. Journal of Psychoactive Drugs 14 (3): 205–20.
Stohler, R., H. Rommelspacher, D. Ladewig, and G. Dammann. 1993. Beta-carboline (Harman/Norharman) sind bei Heroinabhängigen erhöht. Therapeutische Umschau 50:178–81.
β-phenethylamines, PEAs, 2-phenethylamines
β-phenethylamines are derivatives of phenethylamine (Shulgin 1979). The biogenic 2-phenethylamine (PEA) dilates the blood vessels in the brain and consequently can, under certain circumstances, cause headaches or migraines (cf. Theobroma cacao). The most well-known psychoactive β-phenethylamine is mescaline, a component of numerous cacti.
Many cacti (including Gymnocactus spp.492 and Opuntia spp.) contain phenethylamines that are structurally very similar to mescaline but whose effects are practically unknown (West et al. 1974). It is quite possible that such substances as candicine (Trichocereus spp.), hordenine (Ariocarpus spp., Opuntia clavata Eng.; cf. Meyer et al. 1980 and Vanderveen et al. 1974), and macromerine (Coryphantha spp.) produce psychoactive effects when used at the appropriate dosages. This area still offers many opportunities for experimental human pharmacology (Heffter technique). Such experimentation could, for example, lead to a psychoactive use of the South American Noto-cactus ottonis (Lehm.) Berg. [syn. Parodia ottonis] (cf. Hecht 1995, 82), a cactus that is often found at places where cacti are sold, is very easy to grow, and contains hordenine (Shulgin 1995, 16*). The genus Lobivia also contains hordenine (Follas et al. 1977).
Hordenine and related substances (occasionally in high concentrations) are also found in other plants, such as the Himalayan Leguminosae Desmodium tiliaefolium G. Don (Ghosal and Srivastava 1973).
Numerous phenethylamines that have psychoactive effects (both empathogenic and/or psychedelic) have been synthesized (e.g., MDMA, MDA, MMDA, MDE, 2-CB, et cetera; cf. Shulgin and Shulgin 1991*).
Notocactus ottonis, a cactus originally from eastern South America, contains the β-phenethylamine hordenine.
Numerous cacti, including this Melocactus species, contain phenethylamines, some of which have psychoactive properties. (Woodcut from Tabernaemontanus, Neu Vollkommen Kräuter-Buch, 1731)
See also the entries for mescaline.
Follas, W. D., J. M. Cassidy, and J. L. McLaughlin. 1977. β-phenethylamines from the cactus genus Lobivia. Phytochemistry 16:1459–60.
Ghosal, S., and R. S. Srivastava. 1973. β-phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tilaefolium. Phytochemistry 12:193–97.
Meyer, Brian N., Yehia A. H. Mohamed, and Jerry L. McLaughlin. 1980. β-phenethylamines from the cactus genus Opuntia. Phytochemistry 19:719–20.
Shulgin, Alexander T. 1979. Chemistry of phenethylamines related to mescaline. Journal of Psychedelic Drugs 11 (1–2): 41–52.
Vanderveen, Randall L., Leslie C. West, and Jerry L. McLaughlin. 1974. N-methyltryramine from Opuntia clavata. Phytochemistry13:866–67.
West, Leslie G., Randell L. Vanderveen, and Jerry L. McLaughlin. 1974. β-phenethylamines from the genus Gymnocactus. Phytochemistry 3:665–66.
Bufotenin, 5-hydroxy-N,N-dimethyltryptamine, 5-OH-DMT, mappin, N,N-dimethylserotonin, 3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
Empirical formula: C12H16ON2
Substance type: tryptamine (indole alkaloid)
Bufotenine was first isolated in 1893 from secretions of the common toad (Bufo vulgaris L.) (Shulgin 1981). In 1954, it was found in Anadenanthera peregrina. Bufotenine also occurs in the false death cap (Amanita citrina[Schaeff.] S.F. Gray) (Keup 1995, 11; Wieland and Motzel 1953) and in other members of the genus (cf. Amanita pantherina). Indeed, the symbolic relationship between toads and mushrooms is very interesting in this context (see Amanita muscaria). Bufotenine has also been found in Anandenanthera colubrina (Piptadenia spp.), Arundo donax, Banisteriopsis spp., Mucuna pruriens, and Phragmites australis. Bufotenine is a tryptamine derivative and is closely related to N,N-DMT, 5-MeO-DMT, and psilocybin and psilocin. Chemically, it is almost identical to melatonin (for more on melatonin, see Reiter and Robinson 1996).
Bufotenine has been detected in human urine on numerous occasions (Räisänen 1985) and thus we know that it is a natural substance that is metabolized in the human body. The molecule is very stable. Approximately 16 mg is considered to be an effective dosage. The pharmacology of the substance has been little studied.
The first report of the hallucinogenic effects of bufotenine was published by Fabing and Hawkins (1956), who tested the substance on prison inmates (probably against their will). This was followed by additional research with humans, including some studies in which the substance was tested under highly unethical conditions by being injected into patients in a closed psychiatric institution without their permission, or even against their will. The patients were administered overly high doses and also subjected to electroshocks and other procedures. In this setting, no visions were reported. It was concluded that bufotenine does not produce visions but has only toxic effects (Turner and Merlin 1959). Subsequent studies strengthened the theory that bufotenine should not be classified as a hallucinogen (Mandell and Morgan 1971). A more recent study using only one subject found no hallucinogenic effects, although changes in the emotional domain were observed (McLeod and Sitram 185). Almost all of the reports have noted that the faces of the test subjects turned red or even purple (Fabing and Hawkins 1956). The belief that bufotenine is not a true psychedelic drug has persisted into the present day (e.g., Lyttle et al. 1996; this study, however, is not based on any personal experiments). In its pure form, bufotenine has never acquired any cultural significance as a psychoactive substance.
Bufotenine and Bufo marinus
Since ancient times, there have been numerous reports of toads being used to prepare love drinks and other witches’ brews, and even witches’ ointments (Degraaff 1991; Hirschberg 1988). Researchers (prematurely) dismissed such reports as fantasy. In China and Mesoamerica, there is good evidence for the use of toads in magical brews. Chinese toad secretions (ch’an su) contain large amounts of bufotenine (Chen and Jensen 1929). In China and Japan, preparations containing bufotenine are sold as aphrodisiacs (Lewis 1989, 70).493
In Mesoamerica, the toad was regarded as a manifestation of the Earth Mother, for example, in the form of the Aztec earth goddess Tlatecuhtli (Furst 1972; 1974, 88*). In the region, toads (and frogs) are associated with the rain gods (chac) and rainmaking. The Tarahumara refer to toads as “powerful rainmakers.” The Olmecs—whose culture is thought to have been the first Meso-american civilization—depicted toads in their sacred art and probably used them as hallucinogens. An Olmec object made of green jade and shaped like a toad has been interpreted as a tray for snuff powder (Peterson 1990, 46*). In general, the toad was probably the most important Olmec deity (Furst 1981; Furst 1996*; Kennedy 1982; Taylor n.d.).
A cylindrical ceramic container (late Classic period) containing a Bufo marinus (cane toad) skeleton was found in Seibal, a Mayan ceremonial center. It may have been used as a vessel for drinking balche’. Hundreds of ritually interred cane toad skeletons were discovered in post-Classic Mayan ritual depots on the Caribbean island of Cozumel (Hamblin 1981; 1984, 53 ff.). A report from the colonial period indicates that toads were an ingredient in balche’or chicha. Bufo marinus is also an ingredient in zombie poison.
The secretions of Bufo melanostictus contain bufotenine. In traditional Chinese medicine, the crystallized raw drug obtained from these secretions is regarded as an excellent aphrodisiac.
In Mesoamerica, Bufo marinus is known variously as henhen (Tzeltal; cf. Hunn 1977, 247), bab (Mayan), äh bäb (Lacandon), and tamazolin (Aztec). Numerous stone sculptures of toads as well as some toad bones were discovered in the main temple (Templo Mayor) of the Aztecs (Ofrenda 23; Alvarez and Ocaña 1991, 117, 128). All of the finds suggest that Bufo marinus was used in rituals or had a cosmological significance. Today, some Mexican Indians still eat skinned toads, while their secretions are sold at Mexican brujería markets as a love powder. The toad itself is invoked as a love magic in magical prayers (oración del sapo). The toad’s mucus is rolled into little balls that are then rubbed behind the ear as an aphrodisiac. Many people in Mexico still wear toad-shaped amulets today; they may, for example, be made from amber or obsidian from Chiapas.
In the southern part of Veracruz, curanderos (“healers”) or brujos (“sorcerers”) still use a preparation of Bufo marinus. To prepare it, they capture and kill ten toads. The glands are removed and crushed to produce a paste, to which lime (probably slaked lime) and ashes from a botanically unidentified plant called tamtwili are added. The combination is then mixed in water and boiled until there is no more “bad smell” (usually all night long). The solution is then mixed with chicha (maize beer) and filtered. The remaining fluid is kneaded into maize dough, lime brine, and five kernels of sprouted maize, and the mixture is laid out in the sun for a few days so that it can ferment, after which it is dried over a fire. This product (piedrecita, “little rocks”) is then stored far away from any human dwellings. In earlier times, special huts were used to store this magical substance. For consumption, a few pieces are cut off, ground, and soaked in water. After the insoluble ingredients have settled, the solution is poured off and boiled for a considerable time until it gives off a certain odor. Today, the drink is no longer ingested collectively but is used by only one person at a time under the supervision of a curandero. The effects begin after approximately thirty minutes and are first manifested as an increase in the pulse rate and a shaking of the muscles and limbs, followed by headaches and delirium. This state lasts three to five hours. In former times, the drinking of this brew was an important part of the initiation of boys into adulthood. Sacred songs were sung to the initiate while he was delirious. The initiate was told to allow the visions he was going to experience to impress themselves well upon him (Knab n.d.).
It appears that the hallucinogenic effects of Bufo marinus were also known in Argentina, for it is considered there to be one of the “temptations” of Saint Anthony (see Claviceps purpurea) (Rosemberg 1951).
Originally from the Americas, Bufo marinus was introduced to Australia, where it is now known as the cane toad and its secretions are allegedly used as a psychoactive drug. Under Queensland’s Drug Misuse Act, bufotenine is an illegal substance in Australia (Ingram 1988, 66). In recent years, the press has been reporting increasing cases of toad lickin’ (Lyttle 1993), a practice in which the secretions of Bufo marinus are licked off the toad:
When licking the expressed secretions (abusers reported that it is possible to “milk” twice a day), a furry sensation on the lips and tongue quickly becomes manifest. Five to ten (up to 30) minutes later, nausea is common, and only 20 to 30 minutes after ingestion, sometimes earlier, hallucinations of various kinds set in, beginning more rapidly and not lasting as long as with LSD. (Keup 1995, 12)
The thickened juice of boiled animals is also ingested in Australia (Keup 1995, 14). A decoction of the dried skin (known as cane skin tea) is also used (Der Spiegel 32 : 92).
The secretions from Bufo marinus contain catecholamines (dopamine, N-methyldopamine, adrenaline, noradrenaline) and tryptamines (serotonin, N-methyl-serotonin, bufotenine, bufotenidine, dehydrobufotenine), as well as glycoside-like toad toxins (Deulofeu and Rúveda 1971; Lyttle 1993, 523 f.). The skin has been found to contain morphine. The toad toxins (bufotoxine, bufogenine, and bufadienolides) are cardiotoxic and are similar to digitalis in their effects: nausea, vomiting, increase in blood pressure, confusion, and psychotic states (Keup 1995, 12). Smoking is probably the safest method to ingest Bufo marinus secretions, as the burning process apparently destroys the toxic components while leaving the bufotenine intact (Alexander Shulgin, pers. comm.). The ethnobotanist Brett Blosser smoked dried Bufo marinus secretions (approximately 1 mg every few minutes) and reported experiencing tryptamine-like hallucinations similar to those induced by the secretions of Bufo alvarius (cf. 5-MeO-DMT) (B. Blosser, pers. comm.).
The few reports of the effects of smoked toad skin indicate that they are hallucinogenic. One Australian user stated, “I am seeing the world through the consciousness of a toad” (Lewis 1989, 71).
In traditional Chinese medicine, the secretions of various toads (Bufo bufo gargarizans Cantor, Bufo melanostictus Schneider) have long been used as remedies, tonics, and aphrodisiacs. Many of these secretions (secretio bufonis) contain the hallucinogenic constituent bufotenine. (Illustration from the Ch’ung-hsiu cheng-ho pen-ts’ao.)
The common toad (Bufo bufo) was sacred to the Germanic and Baltic peoples. Only with the introduction of Christianity was the toad demonized and declared to be an animal of the devil. The hallucinogenic substance bufotenine was isolated from its secretions. (Woodcut from Gessner, Historia Animalium,sixteenth century.)
“SMOKE IT! At the Police Department of Drugs in Brisbane [Australia] is a Heinz baby food can labeled ‘Venom cane toad, hallucinogenic, bufotenine.’ Inside the can is a dry, flaky, crystalline, brown substance with an unpleasant odor. This substance comes from dried toad skin, which contains natural bufotenine. It can be broken into small pieces and smoked in a water pipe or a simple pipe. It is said to cause an intense hallucinogenic effect which lasts for several hours.”
STEPHANIE LEWIS CANE TOADS: AN UNNATURAL HISTORY
The active constituent bufotenine was first isolated from secretions of the common toad. The heathen tribes of the Baltic region venerated the toad as a goddess. It is possible that they were aware of the psychoactive effect of the toad’s secretions. (Illustration from 1912)
The title and cover art for the Australian rock music sampler Toad Lickin’ alludes to a practice known in northeastern Australia in which hallucinogenic secretions are licked from toads. (CD cover, 1990)
The following species of toads contain significant amounts of bufotenine: Bufo alvarius (cf. 5-MeO-DMT), B. americanus, B. arenarum, B. bufo bufo, B. calamita, B. chilensis, B. crucifer, B. formosus, B. fowleri, B. paracnemis, B. viridis (Deulofeu and Rúveda 1971, 483).
Commercial Forms and Regulations
Bufotenine is marketed as bufotenine hydrogen oxalate. In the United States, bufotenine is classified as a Schedule I drug (Shulgin 1981). In contrast, in Germany it is not considered a narcotic and is not illegal (Körner 1994, 1572*).
See also the entries for Anandenanthera colubrina and 5-MeO-DMT.
Allen, E. R., and W. T. Neill. 1956. Effects of marine toad toxins on man. Herpetologica 12:150–51.
Alvarez, Ticul, and Aurelio Ocaña. 1991. Restos óseos de vertebrados terrestres de las ofrendas del Templo Mayor, ciudad de México. In La fauna en el Templo Mayor, ed. B. Quintanar, 105–46. Mexico City: INAH.
Chen, K. K., and H. Jensen. 1929. A pharmacognostic study of ch’an su, the dried venom of the Chinese toad. Journal of the American Pharmaceutical Association 23:244–51.
Davis, Wade. 1988. Bufo marinus: New perspectives on an old enigma. Revista de la Academia Columbiana de las Ciencies Exactas, Fisicas y Naturales 14 (63): 151–56.
Degraaff, Robert M. 1991. The book of the toad. Rochester, Vt.: Park Street Press.
Deulofeu, Venancio, and Edmundo A. Rúveda. 1971. The basic constituents of toad venoms. In Venomous animals and their venoms, ed. Wolfgang Bücherl and Eleanor E. Buckley, 475–556. New York and London: Academic Press.
Fabing, Howard D., and J. Robert Hawkins. 1956. Intravenous bufotenine injection in the human being. Science 123:886–87.
Furst, Peter T. 1972. Symbolism and psychopharmacology: The toad as earth mother in Indian America. In Religión en Mesoamérica, XII Mesa Redondo, 37–46. Mexico City: S.M.A.
———. 1981. Jaguar baby or toad mother: A new look at an old problem in Olmec iconography. In The Olmec and their neighbors, ed. E. Benson, 149–62. Washington, D.C.: Dumbarton Oaks.
Hamblin, Nancy L. 1981. The magic toads of Cozumel. Mexicon 3 (1): 10–13.
———. 1984. Animal use by the Cozumel Maya. Tucson: The University of Arizona Press.
Hirschberg, Walter. 1988. Frosch und Kröte in Mythos und Brauch. Vienna: Böhlau.
Hunn, Eugene S. 1977. Tzeltal folk zoology. New York: Academic Press.
Ingram, Glen. 1988. The “Australian” cane toad. In Venoms and victims, ed. John Pearn and Jeanette Covacevich, 59–66. Brisbane: The Queensland Museum and Amphion Press.
Kennedy, Alison B. 1982. Ecce Bufo: The toad in nature and Olmec iconography. Current Anthropology 23 (2): 273–90.
Keup, Wolfram 1995. Die Aga-Kröte und ihr Sekret: Inhaltsstoffe und Mißbrauch. Pharmazeutische Zeitung 140 (42): 9–14.
Knab, Tim. n.d. Narcotic use of toad toxins in southern Veracruz. Unpublished manuscript. (Ten typewritten pages.)
Lewis, Stephanie. 1989. Cane toads: An unnatural history. New York: Dolphin/Doubleday.
Lyttle, Thomas. 1993. Misuse and legend in the “toad licking” phenomenon. The International Journal of the Addictions 28 (6): 521–38.
Lyttle, Thomas, David Goldstein, and Jochen Gartz. 1996. Bufo toads and bufotenine: Fact and fiction surrounding an alleged psychedelic. Journal of Psychoactive Drugs 28 (3): 267–90. (Contains an excellent bibliography.)
Mandell, A. J., and M. Morgan. 1971. Indole(ethyl)amine N-methyltransferase in human brain. Nature 230:85–87.
McLeod, W. R., and B. R. Sitram. 1985. Bufotenine reconsidered. Psychiatria Scandinavia 72:447–50.
Räisänen, Martti. 1985. Studies on the synthesis and excretion of bufotenine and N,N-dimethyltryptamine in man. Academic dissertation, Helsinki, University of Helsinki.
Reiter, Russel J., and Jo Robinson. 1996. Melatonin. Munich: Droemer Knaur.
Rosenberg, Tobias. 1951. El sapo en el folklore y en la medicina. Buenos Aires: Editorial Periplo.
Shulgin, Alexander T. 1981. Bufotenine. Journal of Psychoactive Drugs 13 (4): 389.
Taylor, Michael. 1993. The use of the Bufo marinus toad in ancient Mesoamerica. Crash Collusion 4: 53–55.
Turner, W. J., and S. Merlis. 1959. Effects of some indolalkylamines on man. Archives of Neurology and Psychiatry 81:121–29.
Verpoorte, R., Phan-Quôc-Kinh, and A. Baerheim Svendsen. 1979. Chemical constituents of Vietnamese toad venom collected from Bufo melanostictus Schneider. Journal of Ethnopharmacology 1:197–202.
Wieland, Theodor, and Werner Motzel. 1953. Über das Vorkommen von Bufotenin im gelben Knollenblätterpilz. Justus Liebigs Annalen der Chemie 581:10–16.
Cafeina, caféina, caffeina, coffein, coffeinum, guaranin, koffein, methyltheobromin, methyltheo-bromine, 1,3,7-trimethyl-2,6(1H,3H)-purindion, 1,3,7-trimethylxanthine, thein, theine
Empirical formula: C8H10N4O2
Substance type: purine
Caffeine was first isolated from coffee beans (Coffea arabica) and named after the genus. However, this stimulating substance actually occurs in many plants (see the table on page 821). Caffeine has stimulating effects upon the central nervous system because it inhibits the enzyme phosphodiesterase, which inhibits the conversion of endogenous substances (cAMP into AMP). This stimulation is usually accompanied by an increase in heart activity, increased urgency of micturition, sensations of heat, and a rise in body temperature. Vasodilation in the brain dispels tiredness and perception becomes more acute. A normal effective dosage is about 100 mg (equal to approximately one cup of strongly brewed coffee). Undesirable side effects begin to appear at 300 mg unless one is used to this level of consumption. There have been repeated reports of “caffeine addiction” in the United States (Weil 1974). Overdoses of caffeine tend to be unpleasant in nature (cf. Ilex guayusa):
Acute caffeine poisoning causes inebriation-like states of excitation accompanied by ringing in the ears, headaches, dizziness, racing heart, muscle tension, insomnia, restlessness, confusion, deliria, cramps, urge to vomit, diarrhea, urgency of micturition. (Roth et al. 1994, 786*)
It has occasionally been suggested that Catha edulis contains caffeine, but this assumption has never been confirmed and can now actually be ruled out.
Caffeine is used medicinally to treat heart weakness, neuralgia, headaches, asthma, and hay fever and is also administered in homeopathic preparations. It is used as an antidote for poisonings and overdoses of alcohol, nicotine, morphine, and THC.
Commercial Forms and Regulations
Caffeine is available as a pure substance and as caffeine monohydrate. It is a legal substance.
See also the entries for Camellia sinensis, Coffea arabica, Paullinia cupana, and energy drinks.
Blanchard, J., and S. J. A. Sawers. 1983. The absolute bioavailability of caffeine in man. European Journal of Clinical Pharmacology 24:93–98.
Bohinc, P., J. Korbar-Smid, and A. Marinsek. 1977. Xanthine alkaloids in Ilex ambigua leaves. Farmacevtski Vestnik 28:89–96.
Braun, Stephen. 1996. Buzz: The science and lore of alcohol and caffeine. New York and Oxford: Oxford University Press.
Dews, Peter B., ed. 1984. Caffeine. Berlin: Springer.
Freise, F. W. 1935. Vorkommen von Koffein in brasilianischen Heilpflanzen. Pharmazeutische Zentralhalle Deutschlands 76:704 ff.
Gilbert, Richard J. 1981. Koffein—Forschungsergehnisse im Überblick. In Rausch und Realität, ed. G. Völger, 2:770–75. Cologne: Rautenstrauch-Joest-Museum für Völkerkunde.
———. 1988. Caffeine: The most popular stimulant. The Encyclopedia of Psychoactive Drugs. London: Burke Publishing.
Goulart, Frances Sheridan. 1984. The caffeine book: A user’s and abuser’s guide. New York: Dodd, Mead & Co.
Graham, D. M. 1978. Caffeine—its identity, dietary sources, intake and biological effects. Nutrition Reviews 36:97–102.
James, J. E. 1991. Caffeine and health. London: Academic Press.
Lee, Richard S., and Mary Price Lee. 1994. Caffeine and nicotine. New York: The Rosen Publishing Group.
Mosher, Beverly A. 1981. The health effects of caffeine. New York: The American Council on Science and Health.
Partington, David. 1996. Pills, poppers & caffeine. London: Hodder & Stoughton.
Spiller, Gene A., ed. 1984. The methylxantine beverages and foods: Chemistry, consumption, and health effects. New York: Alan R. Liss.
Weil, Andrew. 1974. Caffeine. Journal of Psychedelic Drugs 6 (3): 361–64.
Plants Containing Caffeine
(from Bohinc et al. 1977; Freise 1935; Gilbert 1988; Hartwich 1911*; Mata and McLaughlin 1982*; Schultes 1977b, 123*; Spiller 1984; supplemented)
This French engraving from 1688 depicts the most important caffeinated beverages together with representatives of the cultures of their origin. The South American (on the left) is drinking maté, the Chinese man is drinking tea, and the Muslim sitting to the right is drinking coffee.
Benzoylecgoninmethylester, cocain, cocaïn, cocaina, d-cocain, erythroxylin, kokain, methylbenzoylecgonine, methylbenzylekgonin, (±)-methyl-[3β-benzoyloxy-2α(1αH,5αH)-tropancarboxylate], O-benzoyl-[(–)-ekgonin]-methylester, 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octan-2-carboxylicacidmethylester, 3β-benzoyloxy-2β-tropancarboxylicacid-methylester
Autobahn, blow, C, candy, charlie, coca, coca pura (Spanish, “pure coca”), coco, coke, cousin, do-nuts, doppelter espresso, flake, koks, la blanca, lady snow, la rubiecita, line, linie, mama coca, nasenpuder, nose candy, peach, perica, puro (Spanish, “pure”), schnee, schneewittchen, schniefe, schnupfschnee, sniff, snow, snowwhite, strasse, strässchen, Ziggy’s stardust
In the history of human culture, no other psychoactive plant constituent has had such an impact as cocaine. Because of its enormous cost, however, cocaine is consumed primarily in wealthier circles.
Empirical formula: C17H21NO4
Substance type: coca alkaloid
The cocaine molecule is structurally related to tropine and other tropane alkaloids (Roth and Fenner 1988, 311*). Today, cocaine is the most consumed psychoactive plant constituent in the world. Pure cocaine (as a base) is not water soluble but can be dissolved in alcohol, chloroform, turpentine oil, olive oil, or acetone. Cocaine salts are water soluble.
In 1860, the German chemist Albert Niemann first isolated cocaine from the leaves of the Peruvian coca bush (Erythroxylum coca). The German pharmacist Friedrich Gaedeke (1855) may have represented the alkaloid before this. By around 1870, cocaine was being used as an agent of pleasure, and it was employed at this time to treat alcohol and morphine withdrawal as well as melancholy. The ophthalmologist Karl Koller, a friend of Sigmund Freud, introduced cocaine as a local anesthetic for eye surgery in 1884. Hermann Göring’s use of cocaine was famous, and Adolf Hitler, who also used other stimulants (cf. strychnine), is thought to have consumed cocaine as well (Phillips and Wynne 1980, 112).
Later, other substances derived from cocaine, including eucaine, procaine (= Novocaine), tetracaine (= Pantocaine) (1930), lidocaine (= Xylo-caine) (1944), mepivacaine (= Scandicaine) (1957), prilocain (= Xylonest) (1960), bupivacaine (1963), and etidocain (= Duranest) (1972), were also used as local anesthetics (Büsch and Rummel 1990; Schneider 1993, 19*). Holocaine was also regarded as a substitute.
The goal of chemists and pharmacologists to carve out the effective core of the cocaine molecule and retain the desirable and remove the undesirable effects was achieved in an exemplary manner with the synthesis of procaine (1905). (Büsch and Rummel 1990, 490)
In 1923, Willstädter and his coworkers worked out the complete synthesis of cocaine. The precursors are succindialdehyde, methylamine, and mono-methyl-β-keto-glutarate. However, this synthesis has never achieved pharmaceutical importance. Practically speaking, all of the cocaine used in the pharmaceutical industry is derived from the coca plant. In 1976, 410 kg of cocaine were legally extracted for this purpose (Täschner and Richtberg 1982, 64).
Production and Use
An analysis of thirteen South American Erythroxylum species found that cocaine is present only in Erythroxylum coca and Erythroxylum novogranatense (Holmstedt et al. 1977). Hair analysis of Egyptian mummies has revealed the presence of ecgonin, the first metabolite of cocaine, which indicates that the ancient Egyptians either consumed cocaine or an unknown African plant that metabolizes to ecgonin (Balabanova et al. 1992*).
The coca plantations that are the source of cocaine are known as cocales. Bolivian huanaco leaves (Erythroxylum coca var. coca) are preferred for cocaine production because they are the highest yielding. With good chemicals and chemists, it is possible to produce 1 kg of pure cocaine from 100 kg of coca leaves. In the early 1980s, some 100 tons of pure cocaine were exported from Colombia alone.
The entire process of cocaine production, as well as the smuggling routes, the cartels, and everything from the connections between politicians and the cartels to the consumption of cocaine even by politicians in the White House, has been documented in countless reports on the radio and television and in magazines and well-researched books (Morales 1989). It is difficult to escape the impression that the cocaine saga is one of the best-known stories of our times but one that is officially ignored. Our leaders still act as though the Mafia is using the white powder to corrupt and dominate the world. In reality, the chief benefactors of the billion-dollar business are the banks and the countless politicians and law-enforcement personnel involved in the trade (Sauloy and Le Bonniec 1994).
“Cocaine-using policemen chase cocaine-using pimps away from cocaine-using whores visited by cocaine-using johns, while cocaine-using journalists report about it for their cocaine-using target audiences. I despise all of this: every time I find myself bending over a plate or a mirror with a bill in my nose, I quietly despise myself. When the line is in the brain, this contempt is washed away. When the line is in the brain, the mind becomes deaf and mute. When the line is in the brain, the character turns around.”
HELGE TIMMERBERG “KALTMACHER KOKAIN” [KILLER COCAINE]
The snuffing of crystallized cocaine appears to have been discovered in North America at the beginning of the twentieth century and spread from there. Shortly after 1900, pure cocaine was being ingested together with betel and lime in India, Ceylon (Sri Lanka), and Java. The use of cocaine as an athletic doping agent began in the 1940s (Fühner 1943, 195*). Little has changed since that time. Cocaine dealers still find some of their best customers in the soccer stars of the German first league and sports heroes in the United States.
Basuko is dried cocaine base (an intermediate step in the production of the pure alkaloid). Sucito, or joints made of basuko, have been smoked in Colombia since about 1930 (Siegel l982b, 274). Cocaine is usually produced as a hydrochloride but sometimes also as an oxalate or hypochloride (HCL). Street cocaine is almost exclusively cocaine HCL. Most of the illicit cocaine available in Europe is only about 30% pure, as the expensive pure drug is usually “cut.” The substances that are most commonly used to “cut” cocaine are:
· Inactive additives: milk sugar (lactose), grape sugar (glucose), baking powder, talc (talcum), borax, cornstarch, innositol, mannitol
· Active additives: speed (amphetamine, fenetyllin, ritalin) and “freeze” (novocaine, benzo-caine), PCP (“angel dust”), methedrine, pemoline, yohimbine, lidocaine, procaine, tetracaine, caffeine, quinine, heroin (Täschner and Richtberg 1982, 65; Voigt 1982, 84)
A “line” of cocaine typically contains between 20 and 100 mg of cocaine, depending on the purity of the substance and the consumer’s preference. Many users consume between 2 and 3 g in a day or night. It is said that “the first line of the day is the best.”
Cocaine has been called the champagne of drugs, the drug of high society, the drug of the rich, et cetera, and it is certainly most often associated with the wealthier classes. As a result, consumption of the drug has taken on a strong social character. Cocaine is rarely used by one person alone. When it is taken with others, the consumption follows a rather well-defined ritual. The person providing the costly substance lays out several lines (preferably on a mirror), then takes a currency note (often of high value) and rolls it up. One end of the rolled bill is placed in a nostril and held with one hand, while the other hand is used to press the other nostril closed. Half of one line, or a small line, is then snuffed into the nostril. The person then switches nostrils and snuffs the remaining powder, after which the mirror is passed to the next person. This circle may be repeated several time, and it is customary for each of several participants to prepare lines from their own supply.
The cultural significance of cocaine in the modern world cannot be overlooked. Artists, musicians, and writers use it as a stimulant, while highly paid computer experts, software engineers, and programmers would hardly be able to keep up with the demands of their jobs without their “coke.” Stockbrokers, financial gurus, and election staffers may use cocaine until they are ready to collapse. Even some of the soccer stars who jog into the stadium sporting T-shirts with such incongruous imprints as “Keine Macht den Drogen” (“No Power to Drugs”) are high as a kite on cocaine. According to several estimates, the highest per capita consumption of cocaine is found in Silicon Valley and on Wall Street.
The first literary treatment of cocaine is found in the Sherlock Holmes novel A Scandal in Bohemia, by Sir Arthur Conan Doyle, published only two years after Koller’s discovery (Phillips and Wynne 1980, 45). In this book, the astonishing abilities of this brilliant detective are attributed in part to his use of cocaine. By the time of the following novel, The Sign of the Four, Sherlock Holmes is injecting the pure alkaloid intravenously (Voigt 1982, 38).
The most famous novel of the British writer Robert Louis Stevenson, Dr. Jekyll and Mr. Hyde, was written in only four or six days and nights—with the assistance of the magic powder, of course (Springer 1989, 8; Voigt 1982, 38).
The novellas of the expressionist poet Walter Rheiner (1895–1925), in which he referred to the drug as “the eternal poison” and “the loved and hated poison,” played a great role in shaping the image of demonic seduction by pharmaceutical cocaine (Rheiner 1979).
At the beginning of the twentieth century, the physician Gottfried Benn (1886–1956) wrote and published numerous poems about cocaine (of which he was very fond) that at the time were deemed rather shocking (Benn 1982; vom Scheidt 1981, 401). Many other authors have also been inspired by cocaine, including Georg Trakl, Thomas Zweifel, Josef Maria Frank Fritz von Ostini, Klaus Mann, and Jean Cocteau (Springer 1989).
Cocaine is also the subject of many novels. The classic cocaine novel, Cocaine, was written by Pitigrilli (= Dino Sergè, 1927). The drug has often been treated within its current criminal context (Bädekerl 1983; Fauser 1983), while other novels have been written from a futuristic perspective (Boye 1986). The “coke scene” has also provided a rich source of literary inspiration (McInerney 1984; Ellis 1986).
The famous novel Cocaine, penned by the Italian author Pitigrilli (a pseudonym), is a literary cocaine hallucination that continues to influence the literature inspired by cocaine in the present day. (Cover of an American edition)
“Now look! The shivering stars stand still again, just for a moment.—Sacred poison! Sacred poison!—Tobias sensed and saw the demon standing far above the night sky, as familiar as it was terrifying. He knew and whispered up to the sky: You are death, mercy and life. You have no god beside you.”
WALTER RHEINER KOKAIN [COCAINE] (1918)
“The decomposition of the Self,—how sweet, how deeply desired.
You grant it to me: already my throat is raw,
already the foreign sound has reached
unspoken structures at the foundation of my Self.
“No longer bearing the sword that was born from the mother’s womb.
to fulfill a task here and there
To hit with steely might—: sunken into the heath,
where hills give rest to barely hidden forms!
“A tranquil smoothness, a little something.
And now for the space of a breath
the primordial rises, condensed.
Not-his quake brain showers of mellow impermanence.
“Blasted Self—oh quenched ulcer—
dispersed fevers—sweetly destroyed defense:—
Flow out, flow out!—give birth
with bloodied womb
to the deformed.”
GOTTFRIED BENN DER PSYCHIATER [THE PSYCHIATRIST]
The composer Richard Strauss (1864–1949) wrote his opera Arabella while under the influence of cocaine (Springer 1989, 8; Timmerberg 1996).496 Countless compositions have had cocaine as their subject, including Cocaine Lil, for a mezzo-soprano and four female jazz singers, by the contemporary composer Nancy van de Vate (CD Ensemble Belcanto, Koch, 1994). From the 1920s to the 1940s, the white powder fueled the work of especially jazz and blues musicians, and Chick Webb, Luke Jordan, and Dick Justice even gave it a musical treatment (“Cocaine Blues”).
Veritable blizzards of cocaine have passed through the brains of many of rock music’s greats, who then set their experiences with the “fuel” to music. A few examples are Country Joe McDonald (“Cocaine”), Black Sabbath (“Snowblind”), Little Feat (“Sailin’ Shoes”), the Rolling Stones (“Let It Bleed”), Jackson Browne (“Cocaine”), and David Bowie (“Ziggy Stardust”).
The “hippie” band known as the Grateful Dead sang about the white powder in their song “Truckin’,” one of their few hits to make it onto the charts. Eric Clapton’s interpretation of J. J. Cale’s song “Cocaine” became a worldwide success and has been played millions of times over. The reggae artist Dillinger released an album named Cocaine. The drug also left its mark on the German music scene, influencing or even appearing in the music of Hannes Wader, Konstantin Wecker, Abi Ofarim, and T’MA a.k.a. Falco (“Mutter, der Mann mit dem Koks ist da” [“Mother, the Man with the Coke Is Here”]; BMG Records 1995).
Cocaine has been the subject of at least one theater work: The American playwright Pendleton King wrote a piece entitled Cocaine that was produced for the stage in 1917 (Phillips and Wynne 1980, 93 ff.).
The medicinal applications of cocaine were discovered only a short time after the isolation of the molecule itself. Cocaine was initially used for local anesthesia497 in ophthalmology and dentistry, and infiltration anesthesia was developed just a few years later (Custer 1898). Because analogs (e.g., procaine) were developed that produce specific effects with no psychoactive side effects, cocaine is rarely used as an anesthetic today.
Pharmacology and Effects
Cocaine stimulates the central nervous system, especially the autonomic (sympathetic) system, where it inhibits the reuptake of the neurotransmitters noradrenaline, dopamine, and serotonin and increases the time in which they remain in the synaptic cleft. Cocaine has a powerful effect upon the peripheral nervous system, which explains its efficaciousness as a local anesthetic. It has strong stimulant and vasoconstricting properties. Very high dosages of cocaine are said to be able to induce hallucinations, an effect that is frequently noted in the neurological literature (Pulvirenti and Koob 1996, 49) as well as in prose and poetry (Rheiner 1979, 27). Hallucinations (of nonexistent people, images, flickering lights) often occur during nights in which dosages of 2 to 3 g have been taken. For many people, cocaine also dispels fear. It stimulates a need for alcoholic beverages at the same time that it strongly suppresses the effects of alcohol. A similar dynamic applies to nicotine.
In a certain sense, there is something unsatisfying about the effects of cocaine. A person may sense that satisfaction could be achieved if the effects could possibly be increased. However, using more cocaine does not produce an enhancement of its effects.
Just as coca was and is employed in South America as an aphrodisiac, cocaine has a similar use in the West. Cocaine’s reputation as an aphrodisiac can be traced back to Sigmund Freud (1884) and has been repeatedly confirmed in the pharmacological literature:
At a high level of intoxication, central excitation sets in with characteristic shivering, an initial state of euphoria that turns into delirium and hallucinations. For women, the stimulation . . . not infrequently has an erotic character and has resulted in later accusations of sexual misconduct against the operating physician. (Fühner 1943, 196*)
Some psychiatrists believe that cocaine stimulates the “sexual center” of the brain (Siegel 1982a). For many users, cocaine is inevitably associated with sexuality (MacDonald et al. 1988; Phillips and Wynne 1980, 221).
Cocaine relaxes and opens the sphincter muscles, which makes anal penetration easier as well as substantially more pleasurable. However, cocaine (much like ephedrine) often has an adverse effect on erectile function and consequently leads to temporary impotence (cf. Siegel 1982a).
The addictive potential of cocaine has been the subject of much debate. This issue does not appear to be oriented toward the user as much as it reflects the current legal situation. In recent years, there have been efforts to develop a vaccination against “cocaine addiction.” Of course, the research in this area is conducted on rats (Hellwig 1996). The effect of cocaine on the brain is also an object of much research, since studies that confirm the adverse effects of cocaine are likely to receive financial support from the government. Studies that do not have a political agenda are the exception rather than the rule (Volkow and Swann 1990).
“Look at this shining heap of crystals! They are Hydrochloride of Cocaine. . . . [T]here was never any elixir so instant magic as cocaine. Give it to no matter whom. Choose me the last loser on the earth; take hope, take faith, take love away from him. Then look, see the back of that worn hand, its skin discolored and wrinkled. . . . He places on it that shimmering snow, a few grains only, a little pile of starry dust. The wasted arm is slowly raised to the head that is little more than a skull; the feeble breath draws in that radiant powder. . . . Then happens the miracle of miracles, as sure as death, and yet as masterful as life . . . at least faith, hope and love throng very eagerly to the dance; all that was lost is found.”
ALEISTER CROWLEY COCAINE
The reggae album Cocaine, by the Jamaican artist Dillinger, glorifies not only the white powder but also hemp smoke. (CD cover 1986, Charly Records)
“Mother, the Man with the Coke Is Here,” a German cocaine hit of the Golden Twenties, was recently reissued in a new version with updated lyrics by Falco, a veteran of the Neue Deutsche Welle (“German New Wave”). (CD cover 1995, Sing Sing)
People who use cocaine frequently suffer from a runny nose (“coke sniffles”) the following day. Users may counteract this undesirable and unpleasant aftereffect by rinsing their nose with a saline solution (e.g., with medicinal salts). Many users rub vitamin E oil in their nose, a practice said to regenerate the highly irritated mucous membranes in the nose (Voigt 1982, 72). Although cocaine can be very helpful in dealing with an acute attack of hay fever, chronic use can actually contribute to the condition.
Crack or Free-Base Cocaine
In the German press, crack has been portrayed as “death for a few dollars,” “the devil’s drug from the U.S.A.,” et cetera. The general idea seems to be that “cocaine was a miracle, but crack, crack was better than sex” or “cocaine was purgatory—but crack is hell” (in Wiener 6 : 65, 66).
Crack, which is also known as base, free base, baseball, rocks, Roxanne, and supercoke, is nothing more than smokeable free-base cocaine (Siegel 1982b). In other words, crack is cocaine in the form of a free base (Pulvirenti and Koob 1996, 48). It can be obtained from an aqueous solution of cocaine hydrochloride to which an alkaline substance (such as sodium carbonate) is added. The cocaine salt is transformed into the pure base, or, in other words, the pure substance. It can then be purified with ether, causing the cocaine to crystallize out. Crack is usually “smoked” (i.e., vaporized and inhaled) in glass pipes. A typical dosage ranges from 0.05 to 0.1 g. The effect is very similar to that of snuffed cocaine but is much more intense:
Although crack is a derivative of cocaine, there is little comparison between the mild and mostly stimulating cocaine inebriation and the effects of the short-term crack high, which can literally bowl one over. Whereas cocaine produces a euphoric sensation of great concentration and razor-sharp intelligence for about 20 to 60 minutes, crack lasts for only three to five minutes while giving the consumer an incredibly strong kick with regard to physical sensations as well as the euphoria of absolute omnipotence. Of course, this has resulted in many myths, including one that crack is particularly pure. (Sahihi 1995, 37*)
Ethnologists have begun using the field methods typical of the discipline to study the “crack phenomenon,” which appears to be a typically American product (Holden 1989). “Crack life” is a reflection of the problems in American society and reveals deep social fissures and cultural anomalies. For users, the “crack way” is an important form of identity formation. Crack is frequently found together with prostitution, as “addicts” may accept it as a form of payment for sexual services (Carlson and Siegal 1991).
On the street, the following substances may be used as substitutes for cocaine or crack in times of shortage: procaine, caffeine, benzocaine, phenylpropanolamine, lidocaine, and ephedrine (Siegel 1980).
Commercial Forms and Regulations
Cocaine hydrochloride is available through the pharmacy trade. The German Drug Law lists cocaine as a “narcotic drug in which trafficking is allowed but which may not be prescribed” (Körner 1994, 42). In the United States, the Controlled Substances Act classifies cocaine as a Schedule II substance.
Cocaine was used widely in Germany and Italy during the Golden Twenties. Many cartoonists poked fun at the subject. (Cartoon, Germany, circa 1920)
See also the entries for Erythroxylum coca, Erythroxylum novogranatense, atropine, and tropane alkaloids.
Ashley, Richard. 1975. Cocaine: Its history, use and effects. New York: St. Martin’s Press.
Aurep, B. von. 1880. Über die physiologische Wirkung des Cocaïn. Archiv für Physiologie 21:38–77.
Bädekerl, Klaus. 1983. Ein Kilo Schnee von Gestern. Munich and Zurich: Piper.
Benn, Gottfried. 1982. Gedichte, in der Fassung der Erstdrucke. Frankfurt/M.: Fischer.
Boye, Karin. 1986. Kallocain: Roman aus dem 21. Jahrhundert. Kiel: Neuer Malik Verlag.
Büsch, H. P., and W. Rummel. 1990. Lokalanästhetika, Lokalanästhesie. In Allgemeine und spezielle Pharmakologie und Toxikologie (5th ed.), ed. W. Forth, D. Heuschler, and W. Rummel, 490–96. Mannheim, Vienna, and Zurich: B. I. Wissenschaftsverlag.
Carlson, Robert G., and Harvey A. Siegal. 1991. The crack life: An ethnographic overview of crack use and sexual behavior among African-Americans in a Midwest metropolitan city. Journal of Psychoactive Drugs 23 (1): 11–20.
Crowley, Aleister. 1973. Cocaine. San Francisco: And/Or Press.
Custer, Julius, Jr. 1898. Cocain und Infiltrationanästhesie. Basel: Benno Schwabe.
Ellis, Bret Easton. 1987. Less Than Zero. New York: Random House.
Fauser, Jörg. 1983. Der Schneemann. Reinbek: Rowohlt.
Fischer S., A. Raskin, and E. Uhlenhuth, eds. 1987. Cocaine: Clinical and biobehavioral aspects. New York: Oxford University Press.
Freud, Sigmund. 1884. Über Coca. Centralblatt für die gesamte Therapie 2:289–314. Repr. in Täschner and Richtberg 1982, 206–31 (see below).
———. 1885. Über die Allgemeinwirkung des Cocains. Medizinisch-chirurgisches Centralblatt 20:374–75.
———. 1887. Bemerkungen über Cocainsucht und Cocainfurcht, mit Beziehung auf einen Vortrag von W. A. Hammonds. Wiener medizinische Wochenschrift 37:927–32.
———. 1996. Schriften über Kokain. Frankfurt/M.: Fischer. (Orig. pub. 1884.)
Gay, George R. 1981. You’ve come a long way, baby! Coke time for the new American lady of the eighties. Journal of Psychoactive Drugs 13 (4): 297–318.
Gottlieb, Adam. 1979. The pleasures of cocaine. San Francisco: And/Or Press.
Grinspoon, Lester, and James B. Bakalar. 1985. Cocaine: A drug and its social evolution. Rev. ed. New York: Basic Books.
Hartmann, Walter. 1990. Informationsreihe Drogen: Kokain. Markt Erlbach: Raymond Martin Verlag.
Hellwig, Bettina. 1996. Impfung gegen Cocain? Deutsche Apotheker-Zeitung 136 (4): 46/270.
Holden, Constance. 1989. Streetwise crack research. Science 246:1376–81.
Holmstedt, Bo, Eva Jäätmaa, Kurt Leander, and Timothy Plowman. 1977. Determination of cocaine in some South American species of Erythroxylum using mass fragmentography. Phytochemistry 16:1753–55.
Kennedy, J. 1985. Coca exotics: The illustrated story of cocaine. New York: Cornwall Books.
Koller, Carl [= Karl]. 1884. Über die Verwendung des Cocaïn zur Anästhetisierung am Auge. Wiener medizinische Wochenschrift 34:1276–1278, 1309–11.
———. 1935. Nachträgliche Bemerkungen über die ersten Anfänge der Lokalanästhesie. Wiener medizinische Wochenschrift 85:7.
———. 1941. History of cocaine as a local anesthetic. Journal of the American Medical Association 117:1284.
Lindgren, J.-E. 1981. Guide to the analysis of cocaine and its metabolites in biological material. Journal of Ethnopharmacology 3:337–51.
Lossen, W. 1865. Über das Cocain. Liebig’s Annalen 133:351–71.
MacDonald, P. T., V. Waldorf, C. Reinarman, and S. Murphy. 1988. Heavy cocaine use and sexual behavior. Journal of Drug Issues 18 (3): 437–55.
Maier, Hans Wolfgang. 1926. Der Kokainismus. Leipzig: Thieme.
McInerney, Jay. 1984. Bright Lights, Big City. New York: Knopf.
Morales, Edmundo. 1989. Cocaine: White gold rush in Peru. Tucson and London: The University of Arizona Press.
Niemann, Albert. 1860. Über eine neue organische Base in den Cocablättern. Dissertation, Göttingen University.
Pernice, Ludwig. 1890. Über Cocainanaesthesie. Deutsche medizinische Wochenschrift 16:287.
Phillips, Joel L., and Ronald D. Wynne. 1980. Cocaine: The mystique and the reality. New York: Avon Books.
Plasket, B., and E. Quillen. 1985. The white stuff. New York: Dell Publishing Co.
Pulvirenti, Luigi, and George F. Koob. 1996. Die Neurobiologie der Kokainabhängigkeit. Spektrum der Wissenschaft 2:48–55. (An unethical and nauseating study on animals.)
Rheiner, Walter. 1979. Kokain: Eine Novelle und andere Prosa. Berlin and Darmstadt: Agora Verlag. Repr. 2nd ed., 1982.
Richards, Eugene. 1994. Cocaine true, cocaine blue. New York: Aperture.
Roles, R., M. Goldberg, and R. G. Sharrar. 1990. Risk factors for syphilis: Cocaine use and prostitution. American Journal of Public Health 80 (7): 853–57.
Sabbag, Robert. 1976. Snowblind: A brief career in the cocaine trade. Indianapolis and New York: The Bobbs-Merrill Co.
Sauloy, Mylène, and Yves Le Bonniec. 1994. Tropenschnee—Kokain: Die Kartelle, ihre Banken, ihre Gewinne. Ein Wirtschaftsreport. Reinbek bei Hamburg: Rowohlt.
Siegel, Ronald K. 1978. Cocaine hallucinations. American Journal of Psychiatry 135:309–14.
———. 1980. Cocaine substitutes. New England Journal of Medicine 302:817–18.
———. 1982a. Cocaine and sexual dysfunction: The curse of Mama Coca. Journal of Psychoactive Drugs 14 (1–2): 71–74.
———. 1982b. Cocaine smoking. Journal of Psychoactive Drugs 14 (4): 271–359.
Smith, David E., and Donald R. Wesson. 1978. Cocaine. Journal of Psychedelic Drugs 10 (4): 351–60.
Springer, Alfred, ed. 1989. Kokain: Mythos und Realität—Eine kritisch dokumentierte Anthologie. Vienna and Munich: Verlag Christian Brandstätter.
Täschner, Karl-Ludwig, and Werner Richtberg. 1982. Kokain-Report. Wiesbaden: Akademische Verlagsgesellschaft.
Thamm, Berndt Georg. 1985. Das Kartell: Von Drogen und Märkten—ein modernes Märchen. Basel: Sphinx.
———. 1986. Andenschnee: Die lange Linie des Kokain. Basel: Sphinx.
Timmerberg, Helge. 1996. Kaltmacher Kokain. Tempo 3:34–42.
Turner, Canton E., Beverly S. Urbanek, G. Michael Wall, and Coy W. Waller. 1988. Cocaine: An annotated bibliography. 2 vols. Jackson and London: Research Institute of Pharmaceutical Sciences/University Press of Mississippi.
Voigt, Hermann P. 1982. Zum Thema: Kokain. Basel: Sphinx.
Volkow, Nora V., and Alan C. Swann, eds. 1990. Cocaine in the brain. New Brunswick, N.J.:
Rutgers University Press. (See book review by Ronald Siegel in Journal of Psychoactive Drugs 23 (1; 1991): 93 f.)
vom Scheidt, Jürgen. 1973. Freud und das Kokain. Psyche (Munich) 27:385–430.
———. 1981. Kokain. In Rausch und Realität, ed. G. Volger, 1:398–402. Cologne: Rautenstrauch-Joest Museum für Völkerkunde.
Wesson, Donald R. 1982. Cocaine use by masseuses. Journal of Psychoactive Drugs 14 (1–2): 75–76.
Wolfer, P. 1922. Das Cocain, seine Bedeutung und seine Geschichte. Schweizerische medizinische Wochenschrift 3:674–79.
Codein, codeina, codéine, codeinum, 4,5α-epoxy-3-methoxy-17-methyl-7-morphinen-6α-ol, kodein
Empirical formula: C18H21NO3H2O
Substance type: opium alkaloid
In 1832, codeine was isolated from opium, which has a codeine content of 2 to 3% (see Papaver somniferum). Codeine is also biosynthesized in the roots of Papaver somniferum L. cv. Marianne (Tam et al. 1980). It is possible that trace amounts of codeine can also be found in other Papaver species (Papaver bracteatum, Papaver decaisnei; cf. Papaver spp.) (Theuns et al. 1986). Codeine is also an endogenous neurotransmitter in humans (cf. morphine).
A dosage of 20 to 50 mg produces “general mental stimulation, warmth in the head, and an increase in the pulse rate, as also appear after the consumption of alcohol” (Römpp 1950*). Codeine does not appear to be metabolized in the body and is excreted unchanged.
Because codeine suppresses the urge to cough, its most important pharmaceutical use is in cough syrups. The dosage when codeine is used as a cough suppressant is 50 mg three times a day. A dosage of 100 to 200 mg results in sleep and sedation. Higher dosages elicit effects comparable to those of morphine. The medical literature contains repeated mentions of “codeine addiction.” Codeine “addicts” are said to ingest up to 2 g of codeine daily (Römpp 1950, 115*). Today, codeine is gaining increasing medicinal importance as a substitution therapy for heroin addicts (Gerlach and Schneider 1994). The pharmaceutical industry synthesizes codeine primarily from thebaine, the main active constituent in Papaver bracteatum Lindl. (cf. Papaver spp.) (Morton 1977, 125*; Theuns et al. 1986).
Codeine has acquired a certain significance in the music scene (jazz, rock, psychedelia), primarily as a substitute for heroin or morphine. Buffy Saint-Marie sang about the anguish of her codeine dependence in the song “Cod’ine” (LP It’s My Way! Vanguard Records 1964). Quicksilver Messenger Service later covered the song and made it famous. In the 1990s, the wave band Codeine had several albums out through Sub Pop. Cough syrups498 with a high codeine content were often consumed as inebriants at concerts, festivals, et cetera (usually in combination with alcohol and cannabis) (Bangs 1978, 158).
Commercial Forms and Regulations
Codeine is available as a pure substance and as codeine hydrochloride, codeine phosphate, and codeine phosphate hemihydrate. Codeine is on Schedule III in the United States. Preparations containing codeine (tinctures, cough syrups, et cetera) require a special prescription (i.e., with no refills allowed and/or on special prescription forms). But in other countries, including France, Spain, Nepal, and India, a prescription is still unnecessary and the medicine can be obtained over the counter from any pharmacy.
“And you live off your days on cod’ine And it’s real, real one more time.”
BUFFY SAINT-MARIE “COD’INE”
(LP IT’S MY WAY! 1964)
The album Barely Real, by the American underground band Codeine, provides a clear demonstration of the effects of the opium alkaloid codeine on the artists. The drawn-out melodies, slow rhythms, and restrained monotony make it difficult for the listener to remain awake. (CD cover 1992, Sub Pop)
See also the entries for Papaver somniferum, morphine, and opium alkaloids.
Bangs, Lester. 1978. Ich sah Gott und/oder Tangerine Dream. Rocksession 2:155–58. Reinbek: Rowohlt.
Esser, Barbara. 1998. Vom Regen in die Traufe: Das Verbot des Ersatzstoffs Codein . . . Focus 26 (6): 58–60.
Gerlach, Ralf, and Wolfgang Schneider. 1994. Methadon- und Codeinensubstitution: Erfahrungen, Forschungsergebnisse, Praxiskonsequenzen. Berlin: VWB.
Tam, W. H. John, Friedrich Constabel, and Wolfgang G. W. Kurz. 1980. Codeine from cell suspension cultures of Papaver somniferum. Phytochemistry 19:486–87.
Theuns, Hubert G., H. Leo Theuns, and Robert J. J. Ch. Lousberg. 1986. Search for new natural sources of morphinians. Economic Botany 40 (4): 485–97.
Benzopyrones, coumarines, cumarines, kumarine
Empirical formula: C9H6O2 (= 1,2-benzopyrone)
Substance type: benzopyrone
Coumarin (= chromen-2-on, kumarin, 2H-1-benzopyran-2-on, o-cumar[in]acid lactone), which has a scent like that of vanilla, crystallizes into colorless prisms and is easily soluble in alcohol, ether, and essential oils. Pure coumarin is exuded from what are known as tonka beans, and for this reason it is also called tonka bean camphor. Coumarin is biosynthesized by the hydroxylation of cinnamic acid or coumarin glycoside. Even plants that do not actually contain any coumarin often produce it when they wilt (giving off the smell of hay) or dry (e.g., Anthoxanthum odoratum, Galium odoratum, Sida acuta).
The black seeds (tonka beans) of the South American tonka tree (Dipteryx odorata) exude crystalline, almost pure white coumarin. In Venezuela, the coumarin that is rubbed from the seeds is utilized to aromatize tobacco and snuffs.
Extracts from ripe and wonderfully fragrant vanilla beans are rich in coumarins. Vanilla has a pheromone-like effect on humans, inducing courtship behavior. (Illustration from Hernández, Rerum medicarum Novae Hispaniae, Rome, 1651)
Coumarins in Psychoactive Plants
(from Gray and Waterman 1978; Römpp 1995*; Shoeb et al. 1973; supplemented) Coumarins (e.g., benzofuran) have been found in the following plants with demonstrated or purported psychoactivity:
For plants containing the coumarin derivative scopoletin, see scopoletin.
Umbelliferone, aesculine, and furocoumarin are all coumarin derivatives. More than six hundred natural coumarins are now known. About two hundred coumarins occur in the Family Rutaceae (including the genera Zanthoxylum, Evodia, Ruta, Thamnosma, Dictamnus, Eriostemon, Citrus, and Aegle), where they appear to have great chemotaxonomic importance (Gray and Waterman 1978; Tatum and Berry 1979).
Coumarins occur in some plants that are used for psychoactive purposes (see scopoletin). Coumarin is the substance responsible for the specific taste of woodruff punch, and it is also present in fahan tea (Angraecum fragrans Du Petit-Thouars), which Bibra (1855*) described as psychoactive. Fahan was once used as a substitute for green tea (Camellia sinensis) and was mixed with tobacco (Nicotiana tabacum) and rolled into cigars (Frerichs et al. 1938, 1234*).
High dosages of pure coumarin can cause headaches, dizziness, lethargy, stupor, and even respiratory paralysis (Roth et al. 1994, 796*). Coumarin is said to be toxic to the liver and for this reason was banned as a component or ingredient in food. However, the toxicity is very doubtful, and the alleged carcinogenic effects are also questionable (Marles et al. 1987).
Commercial Forms and Regulations
In the United States, coumarin has been banned as a food additive since 1954. It has been placed in Class 3 of the Swiss Poison List. In Germany, drinking brandies (38% alcohol) are allowed to contain a maximum of 10 mg of coumarin per liter (Roth et al. 1994, 402*).
“Coumarins, which Vogel recently discovered in tonka beans (Diperix [sic] odorata) and Fontana then found in sweet clover (Melilotus officinalis), also occur in woodruff (Asperula odorata). Everyone knows that woodruff is added to wine in many places in Germany and in France because, as it is said, this improves the taste, but in reality this is probably done to make it more stimulating. . . . Nevertheless, it is doubtlessly worthy of notice that both in Africa [the fahan tea] and in Europe, two plants are used as stimulating or exhilarating agents that contain the very same substance that they very likely thank for precisely this stimulating effect.”
ERNST FREIHERR VON BIBRA
DIE NARKOTISCHEN GENUßMITTEL [THE NARCOTIC AGENTS OF PLEASURE]
(1855, 128 f.*)
See also the entries for scopoletin.
Gray, Alexander I., and Peter Waterman. 1978. Coumarins in the Rutaceae. Phytochemistry 17:845–64. (Contains a rich bibliography.)
Marles, R. J., C. M. Compadre, and N. R. Farnsworth. 1987. Coumarin in vanilla extracts: Its detection and significance. Economic Botany 41:41–47.
Mendez, R. D. H., J. Murray, and S. A. Brown. 1982. The natural coumarins. Chichester, U.K.: John Wiley.
Reisch, J., et al. 1968. Über weitere C3-substituierte Cumarin-Derivate aus Ruta graveolens: Daphnoretin und Daphnoretin-methyläther. Planta Medica 15:372–76.
———. 1969. Über die Cumarine der Wurzel von Ruta graveolens. Planta Medica 17:116–19.
Shoeb, Aboo, Rhandhir S. Kapil, and Satya P. Popli. 1973. Coumarins and alkaloids of Aegle marmelos. Phytochemistry 12:2071–72.
Tatum, James H., and Robert E. Berry. 1979. Coumarins and psoralkens in grapefruit peel oil. Phytochemistry 18:500–502.
Baptitoxin, cytiton, laburnin, 1,2,3,4,5,6-hexahydro-8H-1,5-methano-pyrido[1,2α] [1,5]diazocin-8-ol, sophorin, ulexin
Empirical formula: C11H14N2O
Substance type: quinolizidine alkaloid, lupine alkaloid
Cytisine is found in numerous legumes (Leguminosae) (Plugge 1895), such as the rain shower tree (Laburnum anagyroides Medikus [syn. Cytisus laburnum L.]).499
Since cytisine acts to stimulate the central nervous system, states of excitation and confusion (with hallucinations, delirium), muscle spasms, as well as general clonic-tonic spasms in the extremities not infrequently occur. (Roth et al. 1994, 443*)
Cytisine docks to the acetylcholine (ACh) receptors of the central nervous system, the ganglia, and the neuromuscular endplate. The ganglia-blocking effects of cytisine are similar to those of nicotine and can induce strychninelike spasms, especially hallucinations, and even unconsciousness and ultimately death. However, the lethal dosage for humans is unknown (Roth et al. 1994, 801 f.*). The nicotine-like effects also explain the ethnopharmacological use of plants containing cytisine as tobacco substitutes.
Other lupine alkaloids and cytisine derivatives have been found in many plants from the Family Leguminosae, including Lupinus spp. and Echinosophora koreensis Nakai (a close relative of the genus Sophora) (Murakoshi et al. 1977).
Commercial Forms and Regulations
Cytisine is sold in its pure form and is not subject to any regulations (Roth et al. 1994, 802).
The ripe seeds of the golden chain tree (Laburnum anagyroides = Cytisus laburnum) contain up to 3% cytisine. In Germany, the dried leaves of the tree were smoked during the years following World War II as a stimulating substitute for tobacco.
The magnificent flowers of the Philippine jade vine or emerald creeper (Strongylodon macrobotrys A. Gray) contain cytisine and other alkaloids.
“During the World War, the leaves of plants containing cytisine were a popular substitute for tobacco in many countries in which tobacco was not readily available. The toxicity of these plants can be seen in the fact that a cytisus cigarette causes the same nausea to nonsmokers as a real tobacco cigarette does, while those who are used to tobacco do not notice any discomfort.”
MAGISCHE GIFTE [MAGICAL POISONS]
See also the entries for Cytisus spp. and Sophora secundiflora.
Hayman, Alison R., and David O. Gray. 1989. Hydroxynorcytisine, a quinolizidine alkaloid from Laburnum anagyroides. Phytochemistry 28 (2): 673–75.
Murakoshi, Isamu, Kyoko Fukuchi, Joju Haginiwa, Shigeru Ohmiya, and Hirotaka Otomasu. 1977. N-(3-oxobutyl) cytisine: A new lupin alkaloid from Echinosophora koreensis. Phytochemistry 16:1460–61.
Plugge, P. C. 1895. Uber das Vorkommen von Cytisin in verschiedenen Papilionaceae. Archiv für Pharmazie 233:430 ff.
Plugge, P. C., and A. Rauwerda. 1896. Fortgesetzte Untersuchungen Über das Vorkommen von Cytisin in verschiedenen Papilionaceae. Archiv für Pharmazie 234:685 ff.
Seeger, R., and H. G. Neumann. 1992. Cytisin. Deutsche Apotheker Zeitung 132:303–6.
Plants Containing Cytisine
(from Bock 1994, 75 ff.*; Römpp 1995*; Roth et al. 1994*; supplemented)
7-chlor-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-on, sleeping pill, tranquilizer, Valium
Empirical formula: C16H13ClN2O
Substance type: benzodiazepine
Diazepam, better known as Valium, was originally synthesized in the laboratory and introduced as a therapeutic drug (psychopharmaca, tranquilizer) in the 1960s. The substance produces sedative, euphoric, and especially anxiolytic (anxiety-reducing) effects (Henningfield 1988, 17, 35*).
During the investigation of diazepam’s pharmacology, it was discovered that the human nervous system has a special receptor for this molecule, known as the benzodiazepine receptor or the [3H]-diazepam receptor. Luk et al. (1983) found three isoflans in the urine of cattle that may possibly dock (as neurotransmitters) in the benzodiazepine receptor. It is known that the kavapyrones (cf. Piper methysticum) bind to the [3H]-diazepam receptor. Recently, flavonoids in the buds of the South American linden tree (Tilia tomentosa Moench; Tiliaceae; cf. tila) were found to bind to the benzodiazepine receptor. A substance found in Passiflora caerulea L. (cf. Passiflora spp.), 5,7-dihydroxyflavone, also docks to the same location (Viola et al. 1994).
The benzodiazepine receptor has been shown to be present in all vertebrates, suggesting that it appeared at a very early date in the evolution of the nervous system and has been preserved into the present. This indicates that it plays an important function in the nervous system and that there are endogenous substances that bind to it in order to transmit certain messages (Müller 1988).
But what do these substances look like? At first they were thought to be polypeptides, but then traces of diazepam and desmethyldiazepam were discovered in the brains of humans and other animals. Because diazepam and its initial metabolite appear in breast milk and the placenta after the ingestion of Valium (Wessen et al. 1985), it was first believed that the diazepam must have been introduced into the body from outside. But when diazepam was subsequently also found to be present in brains that dated to a time before the discovery of Valium synthesis, it was concluded that diazepam was not a synthetic chemical at all but a naturally occurring neurotransmitter in the nervous system (Müller 1988). Thus it was demonstrated that “Valium, the very symbol of chemical psychopharmaca” (Zehentauer 1992, 121*), is actually a natural substance.
Pharmacologists were surprised when subsequent research demonstrated the presence of diazepam and desmethyldiazepam in potatoes (Solanum tuberosum L.; cf. Solanum spp.) and in such diverse grains as wheat (Triticum aestivum L.; cf. beer), corn/maize (Zea mays), and rice (Oryza sativa L.; cf. sake) (Müller 1988). Valium, in other words, is a natural active constituent in plants. However, the concentration in these plants is so low that a person would likely not notice any Valium effects even after consuming a whole sack of potatoes.
Valium is one of the most widely used sedative drugs in modern society and is normally prescribed for the treatment of anxiety and sleeping disorders.500 Not surprisingly, Valium also finds use as a recreational drug in some circles, particularly in combination with other substances. Its euphoric properties can be greatly affected by alcohol, which can at times counteract the sedative properties, resulting in powerful stimulating effects.
Valium is one of the more commonly used psychopharmaca in the music scene. Several rock bands, including the classic “space rock” band Hawkwind (“Valium 10,” 1978), have dedicated titles to the substance.
Commercial Forms and Regulations
Valium is available by prescription only. In the United States, it is listed as a Schedule IV drug under the Controlled Substances Act.
“The fact that Valium is ultimately 100% natural is not without a certain irony. For many ideologically tinged critics of psychopharmaca, benzodiazepines have become the very symbol of the evils of chemistry for the mind.”
“SIND BENZODIAZIPINE 100% NATUR?” [ARE BENZODIAZEPINES 100% NATURAL?]
The potato (Solanum tuberosum L.), a member of the Nightshade Family, contains highly toxic solanum alkaloids, primarily αsolanine, in all parts of the plant, including the green potatoes and the young sprouts. The tubers have been discovered to contain traces of naturally occurring diazepam. (Woodcut from Tabernaemontanus, Neu Vollkommen Kräuter-Buch, 1731)
Flesch, Peter. 1996. Schlafstörungen bei älteren Patienten: Auf Benzodiazepine kann meist verzichtet werden. Jatros Neurologie 12:6–7 (interview).
Henningsfield, Jack E. 1988. Barbiturates: Sleeping potion or intoxicant. The Encyclopedia of Psychoactive Drugs. London, Toronto, and New York: Burke Publishing Company.
Luk, Kin-Chun, Lorraine Stern, Manfred Weigele, Robert A. O’Brien, and Nena Sprit. 1983. Isolation and identification of “diazepam-like” compounds from bovine urine. Journal of Natural Products 46 (6): 852–61.
Müller, Walter E. 1988. Sind Benzodiazipine 100% Natur? Deutsche Apotheker Zeitung 126 (13): 672–74.
Viola, H., C. Wolfman, M. Levi de Stein, C. Wasowski, C. Pena, J. H. Medina, and A. C. Paladini. 1994. Isolation of pharmacologically active benzodiazepine receptor ligands from Tilia tomentosa (Tiliaceae). Journal of Psychopharmacology 44:47–53.
Wesson, Donald R., Susan Camber, Martha Harkey, and David E. Smith. 1985. Diazepam and desmethyldiazepam in breast milk. Journal of Psychoactive Drugs 17 (1): 55–56.
Diterpene, diterpènes, diterpenoids, diterpenos
Diterpenes are not alkaloids but non-nitrogenous natural substances composed of four isoprene groups. They are related to the monoterpenes and sesquiterpenes and belong to the terpene group. Diterpenes occur in numerous plants and several essential oils.
Some diterpenes regulate plant growth. Termites, sponges (Spongia spongens L.), and coelenterates contain bioactive diterpenes that have inhibiting effects upon certain bacteria (Buchbauer et al. 1990, 28). There are even sweet-tasting diterpenes, such as the natural sweetening agents in Stevia rebaudiana (Bert.) Hemsl., the leaves of which are used to sweeten maté (cf. Ilex paraguariensis).
The first psychoactive diterpene to be discovered was salvinorin A. It is very likely that there are other psychoactive diterpenes that have not yet been isolated, pharmacologically tested, or chemically described. Some psychoactive alkaloids are diterpene derivatives. Aconitine, the primary active constituent in monkshood (cf. Aconitum ferox, Aconitum napellus), is a diterpene alkaloid. Diterpene alkaloids also occur in Delphinium and Spiraea.
See also the entries for Coleus blumei, Salvia divinorum, and salvinorin A.
Buchbauer, Gerhard, Helmut Spreizer, and Gabriele Kiener. 1991. Biologische Wirkungen von Diterpenen. Pharmazie in unserer Zeit 19 (1): 28–37.
Reid, W. W. 1979. The diterpenes of the Nicotiana species and N. tabacum cultivars. In The biology and taxonomy of the Solanaceae, ed. J. G. Hawkes, R. N. Lester, and A. Skelding, 273–78. London: Academic Press.
Diterpenes in Psychoactive Plants
(from Buchbauer et al. 1990; Rein 1979; supplemented)
Aphetonin, efedrina, ephedrin, ephédrine, ephedrinum, ephetonin, erythro-2-methylamino-1-hydroxyl-1-phenylpropane, (1R,2S)-2-methylamino-1-phenyl-1-propanol
Empirical formula: C10H15NO
Substance type: ephedra alkaloid
Ephedrine was first isolated in 1887 by Nagai from Ephedra distachya (cf. Ephedra spp.) and was first introduced into ophthalmology as Mydriaticum (cf. atropine). Since around 1925, the alkaloid also been an important asthma medication (Schneider 1974, 2:54*).
Ephedrine occurs in almost all species of ephedra (cf. Ephedra gerardiana, Ephedra sinensis, Ephedra spp.). Two Malvaceae, Sida acuta Burm. and Sida rhombifolia L. (Sida spp.), which are smoked along the Mexican Gulf Coast as a marijuana substitute (cf. Cannabis indica), also contain ephedrine (Schultes and Hoffmann 1992, 56*). Ephedrine is probably present in other species of Sida as well. Ephedrine has also been found in Aconitum spp., yew (Taxus bacata L.; cf. witches’ ointments), and khat (Catha edulis) (Römpp 1995, 1191*; Roth et al. 1994, 695*).
Ephedrine has sympathomimetic effects and causes an increased excretion of the endogenous neurotransmitter noradrenaline, which is responsible for the stimulant effects (Kalix 1991). Ephedrine hydrochloride has potent stimulant effects; it improves the general mood and may even induce euphoria. These effects can last up to eight hours. It is known that “therapeutic overdoses of ephedrine (Aphetonin) can also cause pronounced states of excitation combined with sexual arousal” (Fühner 1943, 199*). In men, however, ephedrine induces a temporary state of impotence. Ephedrine is a popular doping agent for athletes but is prohibited for this purpose (Körner 1994, 1483*). There have been reports of “ephedrine addiction” (Prokop 1968).
Because ephedrine helps reduce swelling of the mucous membranes, it is a component of many cough syrups (see codeine). Ephedrine suppresses the effects of alcohol and is administered subcutaneously to prevent hypotension during anesthesia (Morton 1977, 35*). Between 55 and 75% of ephedrine is excreted in the urine unchanged (Roth et al. 1994, 812*). The effective oral dosage is 5 to 10 mg.
The closely related ephedra alkaloids have similar effects but vary in their potency (Reti 1953). Pseudoephedrine is significantly weaker, while the related ephedroxanes tend to have depressant effects (Hikino et al. 1985). Pseudoephedrine can be used to produce methcathinone, which in the United States is smoked as “speed” or snuffed like cocaine (it is also used as a substitute for cocaine) (Glennon et al. 1987).
Although Catha edulis does contain d-norisoephedrine, it is not the plant’s primary active constituent, as was previously assumed (Wolfes 1930). However, cathinone, the psychoactive constituent in khat leaves, is metabolized into ephedrinene (Brenneisen et al. 1986; Kalix 1991). Norephedrine, the nor-form (a threo-isomer) of ephedrine, lacks a methyl group on the side chain. Up to 90% of norephedrine is excreted unchanged (Cho and Segal 1994, 58).
Removing the hydroxyl group from the ephedrine molecule by either reduction or β-hydroxylation yields amphetamine (Cho and Segal 1994, 57). Amphetamine is one of the most highly effective stimulants known. Numerous derivatives have been developed from amphetamine (e.g., Ritalin, methamphetamine, MDMA; cf. herbal ecstasy). In addition to their stimulating effects, several of these substances also induce empathogenic and even hallucinogenic effects (Cho and Segal 1994). Amphetamine has not yet been found to occur in nature.
Commercial Forms and Regulations
Ephedrine is available as anhydrous ephedrine (ephedrinum anhydricum), ephedrine hemihydrate, or (most often) ephedrine hydrochloride ([+]-ephedrine-HCL). Ephedrine and ephedrine preparations (medicinal drugs) require a prescription. Because ephedrine is now regarded as a precursor substance for the illegal synthesis of MDMA, it is only rarely prescribed and is strictly controlled. In Germany, only combination preparations (cough medicines) in which a single dosage may not exceed 10 mg of ephedrine can be purchased in a pharmacy without prescription (Roth et al. 1994, 812*). A number of high-profile cases, including one in which a young professional athlete died after ingesting ephedrine before training, resulted in the banning of most ephedrine preparations in the United States in 2004.
Swiss ephedra (Ephedra helvetica) contains ephedrine.
See also the entries for Catha edulis, Ephedra gerardiana, Ephedra sinica, and Ephedra spp.
Brenneisen, R., S. Geisshüsler, and X. Schorno. 1986. Metabolism of cathinone to (–)-norephedrine and (–)-norpseudoephedrine. Journal of Pharmacy and Pharmacology 38:298–300.
Cho, Arthur K., and David S. Segal, eds. 1994. Amphetamine and its analogs: Psychopharmacology, toxicology and abuse. San Diego: Academic Press.
Costa, E., and S. Garattini, eds. 1970. Amphetamine and related compounds. New York: Raven Press.
Glennon, R., M. Yousif, N. Naiman, and P. Kalix. 1987. Methcathinone, a new and potent amphetamine-like agent. Pharmacol. Biochem. Behav. 26:547–51.
Hikino, Hiroshi, Kuniaki Ogata, Yoshimasa Kasahara, and Chohachi Konno. 1984.
Pharmacology of ephedroxanes. Journal of Ethnopharmacology 13:175–91.
Hofmann, H., K. Opitz, and H. J. Schnelle. 1955. Die Wirkung des nor-c-Ephedrins. Arzneimittel-Forshung 5:367–70.
Kalix, P. 1991. The pharmacology of psychoactive alkaloids from Ephedra and Catha. Journal of Ethnopharmacology 32:201–8.
Panse, F., and W. Klages. 1964. Klinischpathologische Beobachtungen bei chronischem Mißbrauch von Ephedrin. Archiv für Psychiatrie und Neurologie 206:69 ff.
Prokop, H. 1968. Halluzinose bei Ephedrinsucht. Der Nervenarzt 1968:71ff.
Reti, L. 1953. Ephedra bases. In The alkaloids: Chemistry and physiology, ed. R. H. F. Manske and H. L. Holmes, 339–62. New York: Academic Press.
Wolfes, O. 1930. Über das Vorkommen von d-Norisoephedrin in Catha edulis. Archiv der Pharmazie 268:81–83.
Ergoline, ergoline alkaloids, ergot alkaloids, ergotalkaloide, mutterkornalkaloide
Ergot alkaloids are derivatives of lysergic acid or clavine derivatives and belong to the group of indole alkaloids. They are found in many climbing plants (Convolvulaceae) and fungi (Claviceps purpurea, Claviceps paspali, Claviceps spp.). The ergot alkaloids can be divided into two groups that exhibit stark pharmacological differences. One group is composed of alkaloids that are highly toxic and cause gangrenous ergotism, while the other group consists of psychoactive alkaloids with hallucinogenic effects. Both types may be present in the same plant (Hofmann 1964).
The following ergot alkaloids have been found in the Convolvulaceae: agroclavine, ergine, ergonovine, isoergine (= isolysergic acid amide), chanoclavine I and II, racemic chanoclavine II, elymoclavine, festuclavine, lysergene, lysergol, isolysergol, molliclavine, penniclavine, cycloclavine, stetoclavine, isostetoclavine, ergometrinine, lysergic acid-α-hydroxyethylamide (= lysergic acid methylcarbinolamide), isolysergic acid-α-hydroxyethyl-amide (= isolysergic acid methylcarbinolamide), ergosine, and ergosinine (cf. Argyreia nervosa, Convolvulus tricolor, Ipomoea violacea, Ipomoea spp., Turbina corymbosa).
One hallucinogenic ergot alkaloid is ergonovine (ergometrine, D-lysergic acid-L-2-propanolamide, ergobasin, ergotocine, ergostetrine, ergotrate, syntometrine, N-[α-(hydroxymethyl)ethyl]-D-lysergic amide). Ergonovine maleate is psychoactive at dosages between 3 and 10 mg (Bigwood et al. 1979). The semi-synthetic methylergonovine has also been reported to induce psychoactive effects (Ott and Neely 1980).
Ergine (= lysergic acid amide, LSA, lysergic amide, 9,10-didehydro-6-methylergoline-8 β-carboxamide) induces psychoactive effects reminiscent of those produced by LSD (lysergic acid diethylamide). LSD is a slight chemical variant of lysergic acid amide that can be produced from ergot (Claviceps purpurea). LSD is a psychopharmaca, a “remedy for the soul” (Albert Hofmann) whose entheogenic effects are very well known (Hofmann 1979*).
The ergot alkaloids dihydroergotaminemesilate, dihydroergotamintartrate, ergometrine hydrogen-maleate, and ergotamine tartrate have a variety of uses in medicine, including as treatments for labor contractions and migraines.
Commercial Forms and Regulations
Ergonovine requires a prescription. In the United States, ergine is a controlled substance (Ott 1993, 437*). LSD is illegal throughout the world.
Lysergic acid amide (LSA)
Lysergic acid diethylamide (LSD)
Saint Anthony is the patron saint of people afflicted with Saint Anthony’s fire, a severe condition caused by the ingestion of ergot alkaloids. (Statue in Cloister Unterlinden, Colmar, Elsass)
See also the entries for Claviceps paspali, Claviceps purpurea, and indole alkaloids.
Bigwood, Jeremy, Jonathan Ott, Catherine Thompson, and Patricia Neely. 1979.
Entheogenic effects of ergonovine. Journal of Psychedelic Drugs 11 (1–2): 147–49.
Hofmann, Albert. 1964. Die Mutterkorn-Alkaloide. Stuttgart: Enke. Ott, Jonathan, and Patricia Neely. 1980. Entheogenic (hallucinogenic) effects of methylergonovine. Journal of Psychedelic Drugs 12 (2): 165–66.
Rivier, L. 1984. Ethnopharmacology of LSD and related compounds. In 50 years of LSD: Current status and perspectives of hallucinogens, ed. A. Pletscher and D. Ladewig, 43–55. New York and London: Parthenon Publishing.
Yui, T., and Y. Takeo. 1958. Neuropharmacological studies on a new series of ergot alkaloids. Japanese Journal of Pharmacology 7:157.
Aroma, ätherische öle, ätherischöl, essence, essenz, etherisches öl, volatile oil
Essential oils are complex mixtures of carbohydrates, alcohols, ketones, acids and esters, ethers, aldehydes, and sulfur compounds that are volatile and evaporate at low temperatures. Essential oils can exhibit tremendous variation in their composition. Each specific mixture produces its own characteristic scent. For the most part, essential oils are distilled from raw drugs or stock plants through a variety of techniques. Essential oils are used medicinally in what has become known as aromatherapy. This healing system was founded by René-Maurice Gattefossé (1881–1950) and is gaining increasing recognition throughout the world (Carle 1993; Henglein 1985; Kraus 1990; Strassmann 1991).
Many psychoactive plants contain essential oils. They are sometimes the only active constituents, while sometimes they occur only in trace amounts. Several components are present in the essential oils of most plants that have unequivocal psychoactive effects.
Eugenol is known to be stimulating, anesthetic, and psychoactive (Sensch et al. 1993; Toda et al. 1994). High concentrations of eugenol occur in the essential oil of clove (Syzygium aromaticum).
Myristicin is regarded as the hallucinogenic component of many essential oils (Wulf et al. 1978, 271). Myristicin is present in dill (Anethum), lovage (Levisticum officinale), parsnips (Pastinaca sp.), and parsley (Petroselinum crispum). The essential oil of the Australian Zieria species (Rutaceae) contains up to 23.4% myristicin. It is thought that myristicin is metabolized into an amphetamine derivative (MDA) (cf. Myristica fragrans).
Safrole is found in cloves (Syzygium aromaticum) and in the sassafras tree (Sassafras albidum). Safrole is one of the most important precursors for the synthesis of MDMA and other similar substances (MMDA, MDE, MDA). The halogen derivatives of safrole, the closely related piperonal and isosafrole, are also suitable for this purpose (Yourspigs 1995). In the body, safrole is thought to be metabolized into amphetamine derivatives.
In nature, thujone exists in two forms: α-thujone and β-thujone. The common tansy (Tanacetum vulgare), whose name is derived from the Greek word athanaton (“immortal”), is very rich in thujone (= tanacetone; cf. Semmler 1900). According to myth, Ganymede became immortal because he had eaten tansy (Albert-Puleo 1978, 65).
The Romans held rosemary (Rosmarinus officinalis) in high esteem as an incense; it contains an essential oil with psychoactive constituents.
Cloves are the flower buds of a tropical tree (Syzygium aromaticum [L.] Merr. et L.M. Perry). They contain a great quantity of an essential oil with anesthetic and stimulating properties; the oil consists primarily of eugenol.
The Western or giant red cedar (Thuja plicata), also known as the giant arborvitae, contains an essential oil that is rich in thujone and can be potently inebriating.
The Moroccan cedar (Cedrus atlantica) has been found to contain thujone.
Clary sage (muscatel sage) (Salvia sclarea L.) has a high thujone content. During the nineteenth century, this plant was used in England instead of hops (Humulus lupulus) to produce a more potent type of beer. Other plants that contain thujone (Artemisia absinthium, Artemisia vulgaris) were used for the same purpose (Albert-Puleo 1978, 69).
Thujone kills the common roundworm Ascaris lumbricoides (Albert-Puleo 1978, 65). The pharmacological effects of thujone are very similar to those of THC (cf. Artemisia absinthium).
It has often been reported that ud oil, the essential oil in lignum aloe or aloe wood (Aquillaria agallocha Roxb. [syn. Aquillaria malaccensis Lam.]; Thymeleaceae), can induce psychoactive effects:
As an incense or aromatic oil, it is used to treat mental and psychological disturbances as well as emotional instability, particularly in cases when this has been produced by negative mental energies. Our experience indicates that aloe wood has unusually relaxing and mood-enhancing properties. It produces a state of trance and introspection and lifts the mind to higher plains of perception. It facilitates the attainment of high levels in meditation. For this reason, it should not necessarily be used prior to a work-filled day in which concentration and quick reactions are required. (Ashisha and Mahahradanatha 1994, 10)
Sufis utilize the precious lignum aloe or distilled ud oil (essence) for advanced stages of Islamic mysticism:
One could say that only those individuals whose minds are more highly developed experience the benefits of ud. In fact, it is only used to treat imbalances during the last three states of mental development. (Moinuddin Chishti 1991, 118*)
Plants Containing Psychoactive Essential Oils
(from Albert-Puleo 1978; Bock 1994*; supplemented)
The Southeast Asian ylang-ylang tree (Cananga odorata) is the source of an essential oil with a sweet, pungent aroma that is used in tantric rituals as an aphrodisiac and has also been shown to have psychoactive effects.
Early European illustration of the American tuberose (Polianthes tuberosa), which produces a valuable essential oil with an enchanting scent. (Woodcut from Gerard, The Herball or General History of Plants, 1633)
The essential oil of sage (Salvia officinalis) contains constituents with inebriating properties.
“Coriander was one of the first spices used by man. Its seeds have been found in Bronze Age ruins on Thera (Santorini) and Therasia as well as in the graves of pharaohs, and we know that it was cultivated in Assyria and Babylon. The Egyptians added it to wine to potentiate its inebriating effects. It used in India during religious and magical ceremonies. The Hebrews called it gad and were very fond of it. In Mycenae, one of the oldest cities in Greece, it was used as a spice to improve bland meals. The Romans believed that the coriander from Egypt was the best and they used it to spice their bread and stews and knew it as an ingredient in their Roman bouquet garni.”
WACHTEL, TRÜFFEL, SCHOKOLADE [GAME HENS, TRUFFLES, CHOCOLATE] (1996, 195 f.*)
“Let my soul inhabit various flowers,
let it become inebriated on their scent,
only too soon will I have to depart crying,
to stand before the face our mother in the kingdom of the dead.”
AZTEC SONG IN ANCIENT NAHUATL POETRY (BRINTON 1887, 79*)
Aromatic lignum aloe (lignum aquillariae resinatum) contains p-methoxycinnamic acid, agarotetrol, and the sesquiterpenoids agarol, agarospirole, α- and β-agarofurane, dihydroagarofurane, 4-hydro-dioxydihydroagarofurane, and oxo-nor-agarofuran, among other constituents.
Essential Oils as Aphrodisiacs
Some essential oils are attributed with aphrodisiac effects. Perfume manufacturers consider the aroma of the Mexican tuberose (Polianthes tuberosa L.; Agavaceae) (cf.Dressler 1953,144*) to be aphrodisiac.
The evergreen ylang-ylang tree (Cananga odorata [Lam.] Hook. f. et Thoms. [f. genuina] [syn. Canangium oderatum Baill.]), which thrives only in tropical regions, is the source of the oil of the same name. In India, ylang-ylang oil is regarded as the favorite oil for tantric rituals because it is believed to have potent aphrodisiac effects and to stimulate and refine erotic sensations. Today, individuals throughout the world use ylang-ylang oil to ritualize their own eroticism (Huron 1994; Kraus 1990; Strassmann 1991). The flowers contain 1.5 to 2.5% of an essential oil composed of linalool, safrole, eugenol, geraniol, pinene, cadinene, and sesquiterpenes. There have been frequent reports of ylang-ylang having mind-altering powers. Pharmacologically, this effect is probably due to the safrole component of the essential oil (Rätsch 1996). Above a certain concentration, safrole appears to produce psychoactive effects that are quite similar to those of MDMA (see herbal ecstasy).
“It has been said that a Sufi attar, a maker of aromatic essences, one day reached the Fardaws region, the highest of the heavens, while performing his mystic exercises. When he arrived there, he smelled a certain scent. After returning to his normal state of mind, he concocted a similar aroma, and this is the origin of the name: ‘gate to the highest heavens’ [jannat al-Fardaws].”
SHAYKH HAKIM MOINUDDIN CHISHTI THE BOOK OF SUFI HEALING
“And on that meadow is a tree
which is of such beauty to behold.
Its roots are galanga and ginger,
its branches are pure white turmeric,
and its flowers are of delicate nutmeg,
the bark is sweet aromatic cinnamon,
the fruits are wonderfully scented cloves.
You also find plenty of cubeb.”
“THE BALLAD OF THE LAND OF PLENTY” (IRELAND, FOURTEENTH CENTURY)
IN SCHLARAFFENLAND [LAND OF MILK AND HONEY]
(RICHTER 1984, 137)
Asarabacca (Asarum europaeum L.; Aristolochiaceae) is rich in the psychoactive asarone. (Woodcut from Fuchs, Läebliche abbildung und contrafaytung aller kreüter, 1545)
See also the entries for Artemisia absinthium, Artemisia spp., Myristica fragrans, herbal ecstasy, and incense.
Albert-Puleo, Michael. 1978. Mythobotany, pharmacology, and chemistry of thujone-containing plants and derivatives. Economic Botany 32:65–74.
Ashisha, Ma Deva, and Mahahradantha. 1994. Duftkräuter und ätherische Öle in der ayurvedischen Heilkunst. Tostedt: Yogini Verlag.
Carle, Reinhold. 1993. Ätherische Öle—Anspruch and Wirklichkeit. Stuttgart: WVG.
Chandler, R. F., S. N. Hooper, and M. J. Harvey. 1982. Ethnobotany and phytochemistry of yarrow, Achillea millefolium, Compositae. Economic Botany 36 (2): 203–23.
Cipolla, Carlo M. 1992. Allegro ma non troppo. Frankfurt/M.: Fischer.
Dandiya, P. C., and M. K. Menon. 1963. Effects of asarone and β-asarone on conditioned responses, fighting behaviour and convulsions. British Journal of Pharmacology 20:436–42.
———. 1964. Actions of asarone on behaviour, stress hyperpyrexia and its interaction with central stimulants. Journal of Pharmacology and Experimental Therapeutics 145:42–46.
Gattefossé, René-Maurice. 1994. Aromatherapie. Aarau: AT Verlag.
Harnishfeger, Götz. 1994. Thuja. In Hagers Handbuch der pharmazeutischcn Praxis, 5th ed., 6:955–66. Berlin: Springer.
Hengelein, Martin. 1985. Die heilende Kraft der Wohlgerüche and Essenzen. Munich: Schönbergers.
Hurton, Andrea. 1994. Erotik des Parfums: Geschichte und Praxis der schönen Düfte. Frankfurt/M.: Fischer.
Kraus, Michael. 1991. Ätherische Öle für Körper, Geist and Seele. Gaimersheim: Simon und Wahl.
Kremer, Bruno P. 1988. Duft und Aromapflanzen. Stuttgart: Franckh-Kosmos.
Laatsch, Hartmut. 1991. Wirkung von Geruch und Geschmack auf die Psyche. In Jahrbuch des Europäischen Collegiums für Bewußtseinsstudien (1991), 119–33. Berlin: VWB.
Miller, Richard Alan, and Iona Miller. 1990. Das magische Parfum. Braunschweig: Aurum.
Morwyn. 1995. Witch’s brew: Secrets of scents. Arglen, Penn.: Whitford Press/Schiffer Publishing. Rätsch, Christian. 1996. Ylang-Ylang, “die Blume der Blumen.” Dao 6:68.
Richter, Dieter. 1984. Schlaraffenland. Cologne: Diederichs.
Rimmel, Eugene. 1985. Das Buch des Parfums. Dreieich: Hesse und Becker. (Orig. pub. 1864.)
Schivelbusch, Wolfgang. 1983. Das Paradies, der Geschmack und die Vernunft. Frankfurt/M.: Ullstein.
Semmler, F. W. 1900. Über Tanaceton und seine Derivate. Berichte der Deutschen Chemischen Gesellschaft 33:275–77
Sensch, O., W. Vierling, W. Brandt, and M. Reiter. 1993. Calcium-channel blocking effect of constituents of clove oil. Planta Medica 59 suppl.: A687.
Strassmann, René A. 1991. Duftheilkunde. Aarau: AT Verlag.
Toda, Shizuo, Motoyo Ohnishi, Michio Kimura, and Tomoko Toda. 1994. Inhibitory effects of eugenol and related compounds on lipid peroxidation induced by reactive oxygen. Planta Medica 60:282.
Wieshammner, Rainer-Maria. 1995. Der 5. Sinn: Düfte als unheimliche Verführer. Rott am Inn: F/O/L/T/Y/S Edition.
Wulf, Larry W., Charles W. Nagel, and Larry Branen. 1978. High-pressure liquid chromatographic separation of the naturally occurring toxicants myristicin, related aromatic ethers and falcarinol. Journal of Chromatography 161:271–78.
Yourspigs, U. P. 1995. The complete book of ecstasy. 2nd ed. N.p.: Synthesis Books.
Dimethyl-5-methoxytryptamine, 5-methoxy-DMT, 5-methoxy-N,N-dimethyl-tryptamine, O-methylbufotenine, 3-[2-(dimethylamino)ethyl]-5-methoxy-indole, toad foam
Empirical formula: C13H18N2O
Substance type: tryptamine (indole alkaloid)
5-MeO-DMT was first discovered in Dictyoloma incanescens DC. and later was isolated from Anadenanthera peregrina as well. It occurs in a very large number of plants, often in association with N,N-DMT (see the table on pages 853–854). Its effects are somewhat more potent than those of N,N-DMT. When the two are administered simultaneously, 5-MeO-DMT more quickly occupies the specific receptors. 5-MeO-DMT is a natural neurotransmitter in the human nervous system. When 5-MeO-DMT (10 to 20 mg) is smoked or vaporized and inhaled, the effects are almost immediately apparent, are incredibly extreme, and last about ten minutes. Many people report having shamanic experiences with this substance as well as experiencing states of enlightenment and the clear light of nirvana (Metzner 1988).
The Colorado River toad (Bufo alvarius) is native to the area around Tucson, Arizona. These toads spend nine months of the year underground, buried in the mud that keeps them protected from the burning desert sun. The toads emerge from their hiding places with the first rains and begin their courtship (Smith 1982, 97–100). They remain visible for only three months. Like all toads, Bufo alvarius develops mucous secretions in two glands that are located on the neck The secretions of the Colorado River toad, however, do not contain bufotoxine, the toxic substance that is found in the secretions of most other toads. Instead, the dried mass contains 15% 5-MeO-DMT (Erspamer et al. 1965, 1967).
The native tribes that lived in the North American Southwest made fetishes of this Bufo alvarius. However, it was only in recent times that the toad’s cultural importance and its psychedelic use were discovered, or more likely rediscovered (cf. Davis and Weil 1992). The toad is “milked” by being held firmly without being crushed. Both glands are then massaged gently until a fat stream of the secretion squirts out. The secretion is caught on a piece of glass, where it is allowed to dry and crystallize. The yellowish crystalline mass then can be scraped off, mixed with different herbs (such as damiana [Turnera diffusa]), and smoked. The toad, which is released unharmed, is quickly able to replenish the loss in its secretions.
When taken orally, Bufo alvarius secretions are apparently toxic, whereas they are not poisonous when smoked (Weil and Davis 1994). Davis and Weil have suggested that the dried secretions of Bufo alvarius were traded to Mexico in pre-Columbian times and that the priests and shamans there smoked or used it in some other manner (Davis and Weil 1992; cf. balche’, bufotenine).
In Arizona, there is now a Church of the Toad of Light, which uses the secretions of Bufo alvarius as a sacrament (Most 1984; Ott 1993, 396*).
Commercial Forms and Regulations
Pure 5-MeO-DMT is available from chemical suppliers. While the substance is not explicitly mentioned in the narcotics laws, the fact that it could be interpreted as a DMT analog may result in problems with the law.
“We sat in a circle with some friends and smoked a joint of toad secretions. I inhaled deeply and passed the joint on. Immediately, a mandala unfolded before me. A dragon was sitting in each corner, and in the circle in the center was a cyclone. No sooner had I recognized the cyclone than I was pulled into it. The cyclone was turning in a clockwise direction—and yet time was going backward. Dragons, amphibians, and dinosaurs appeared in the cyclone, and they too were pulled into eternity. At first, I was surprised that Tibetan dragons and dinosaurs were appearing together in the waves, but then I realized that they represented two metaphors for the same principle. I was drawn further and further along by the deluge of images until I finally arrived at the journey’s end. I sat like a toad or a newt in a Permian bog. The water around me was black, and in the murky fog I saw gigantic ferns and horsetails. Somehow, I communicated with the strange amphibians and realized that I was able to communicate not only with beings of another kind but also across the barriers of time, across millions of years.”
AN EXPERIENCE WITH BUFO ALVARIUS SECRETIONS 
The Colorado River toad (Bufo alvarius) lives only in Arizona. Its secretions contain high concentrations (up to 15% of dry weight) of 5-MeO-DMT.
This drawing depicts the experience of a volunteer subject after smoking 5-MeO-DMT.
See also the entries for bufotenine.
Davis, Wade, and Andrew T. Weil. 1992. Identity of a New World psychoactive toad. Ancient Mesoamerica 3:51–59.
Erspamer, V., T. Vitali, M. Roseghini, and J. M. Cei. 1965. 5-methoxy and 5-hydroxyindolalkylamines in the skin of Bufo alvarius. Experientia 21:504.
———. 1967. 5-methoxy- and 5-hydroxyindoles in the skin of Bufo alvarius. Biochemical Pharmacology 16:1149–64.
Metzner, Ralph. 1988. Hallucinogens in contemporary North American shamanic practice. In Proceedings of the Fourth International Conference on the Study of Shamanism and Alternate Modes of Healing (Independent Scholars of Asia), 170–75.
Most, A. 1984. Bufo alvarius: The psychedelic toad of the Sonoran Desert. Denton, Texas: Venom Press.
Rätsch, Christian. 1993. Die Krötenmutter. In Naturverehrung und Heilkunst, ed. C. Rätsch, 125–28. Südergellersen: Bruno Martin.
Smith, Robert L. 1982. Venomous animals of Arizona. Bulletin 8245. Tucson: The University of Arizona.
Weil, Andrew T., and Wade Davis. 1994. Bufo alvarius: A potent hallucinogen of animal origin. Journal of Ethnopharmacology 41:1–8.
Harmaline and Harmine
Harmaline: 4,9-dihydro-7-methoxy-1-methyl-3H-pyriol [3,4-b] indole, harmalin, harmalolmethylester, harmidin, harmidin, 3,4-dihydroharmin
Harmine: banisterin, banisterine, harmin, 7-methoxy-1-methyl-β-carboline, telepathin, telepathine, yageine
Empirical formula: C13H14N2O (harmaline), C13H12N2O (harmine)
Substance type: β-carbolines, harmala alkaloids (indole alkaloids)
Harmaline and harmine are found in Banisteriopsis caapi and Peganum harmala (Beringer 1928; Beringer 1929; Chen and Chen 1939). Harmine also occurs in numerous other plants (see ayahuasca analogs). Harmaline and harmine not only are strong MAO inhibitors (Pletscher et al. 1959; cf. β-carbolines) but also have antibacterial properties (Ahmad et al. 1992). Harmine was an early treatment for Parkinson’s disease (Halpern 1930b):
Harmine lessens the exaggerated excitability of the parasympathetic system in Parkinson’s patients, increases the low excitability of the sympathetic system, also promotes the excitability of the vestibular apparatus, and puts the patient in a state of euphoria, helping them to better accept their affliction. (Roth et al. 1994, 548*)
In the 1960s, the Chilean psychiatrist Claudio Naranjo (1969*) introduced harmaline and harmine to psychotherapy as “fantasy-increasing drugs” (cf. ibogaine). The extent to which these substances are psychoactive is questionable. To investigate the supposed “psychedelic” effect of harmine,
Maurer (together with Lamparter and Dittrich) tested the hypothesis that harmine is a hallucinogen in 11 self-experiments with a sublingual dosage between 25 and 750 mg. Contrary to expectations, however, harmine did not prove to be a substance that exhibited many similarities to classic hallucinogens such as mescaline or psilocybin. Maurer characterized the state that harmine induced as more of a retreat from one’s surroundings and as a pleasant relaxation with a mildly reduced ability to concentrate. Short-term and elementary optic hallucinatory phenomena were observed only to the degree that they would otherwise also appear naturally during reduced contact with one’s surroundings. With dosages above 300 mg, such undesirable vegetative and neurological symptoms as dizziness, nausea, and ataxia became more apparent, precluding any increase in dosage above 750 mg. (Leuner and Schlichting 1986, 170*)
Crystallized harmaline has a characteristic light yellow color. (Photo: Karl-Christian Lyncker)
Most experimenters have called into question the reports that Naranjo (1979*) published from his psychotherapeutic practice. It may be that he administered ayahuasca, and not any pure substances, to his patients.
Today, harmaline and harmine are primarily used in the production of pharmahuasca (ayahuasca analogs).
Commercial Forms and Regulations
Both substances are available through chemical suppliers. They may be purchased without restriction and are not subject to any legal regulations (Ott 1993, 438*).
See also the entries for Banisteriopsis caapi, Peganum harmala, ayahuasca, ayahuasca analogs, β-carbolines, and indole alkaloids.
Ahmad, Aqeel, Kursheed Ali Khan, Sabiha Sultana, Bina S. Siddiqui, Sabira Begum, Shaheen Faizi, and Salimuzzaman Siddiqui. 1992. Study of in vitro antimicrobial activity of harmine, harmaline and their derivatives. Journal of Ethnopharmacology 35:289–94.
Beringer, Kurt. 1928. Über ein neues, auf das extra-pyramidal-motorische System wirkendes Alkaloid (Banisterin). Der Nervenarzt 1:265–75.
———. 1929. Zur Banisterin und Harminfrage. Der Nervenarzt 2:545–49.
Beringer, Kurt, and K. Willmanns. 1929. Zur Harmin-Banisterin Frage. Deutsche medizinische Wochenschrift 55:2081–86.
Chen, A. L., and K. K. Chen. 1939. Harmine: The alkaloid of caapi. Quarterly Journal of Pharmacy and Pharmacology 12:30–38.
Halpern, L. 1930a. Über die Harminwirkung im Selbstsversuch. Deutsche medizinische Wochenschrift 56:1252–54.
———. 1930b. Der Wirkungsmechanismus des Harmins und die Pathophysiologie der Parkinsonschen Krankheit. Deutsche medizinische Wochenschrift 56:651–55.
Manske, R. H. F., et al. 1927. Harmine and harmaline: Part IX: A synthesis of harmaline. Journal of the Chemical Society (Organic) (1927): 1–15.
Pennes, H. H., and P. H. Hoch. 1957. Psychotomimetics, clinical and theoretical considerations: Harmine, WIN-2299 and nalline. American Journal for Psychiatry 113:887–92.
Pletscher, A., et al. 1959. Über die pharmakologische Beeinflussung des Zentralnervensystems durch kurzwirkende Monoaminooxydasehemmer aus der Gruppe der Harmala-Alkaloide. Helvetica Physiologica et Pharmacologica Acta 17:202–14.
Späth, E., and F. Lederer. 1930. Synthese der Harma Alkaloide: Harmalin, Harmin und Harman. Berichte der deutschen chemischen Gesellschaft 63:120–25.
Endabuse, ibogain, ibogaina, ibogaïne, NIH 10567, 12-methoxy-ibogamin, 12-methoxy-ibogamine
Empirical formula: C20H26N2O
Substance type: indole alkaloid, indole alkylamine, ibogane type
Chemically, ibogaine is closely related to the β-carbolines, and particularly to harmaline and harmine. It belongs to the group of cyclic tryptamine derivatives.
Ibogaine was first isolated from the root cortex of Tabernanthe iboga in France in 1901 (Dybowsky and Landgren 1901). Ibogaine and analogous alkaloids (ibogane type) also occur in Pandaca retusa(Lam.) Mgf. [syn. Tabernaemontana retusa (Lam.) Pichon] (cf. Tabernaemontana spp.), a dogbane species native to Madagscar (Le Men-Olivier et al. 1974). Many genera in the Family Apocynaceae, including Tabernaemontana, Voacanga spp., Stemmadenia, Ervatamia, and Gabunea, contain ibogaine-type indole alkaloids (ibogamine, tabernanthine, voacangine, ibogaline) (Prins 1988, 5).
Between 1940 and 1950, most research into ibogaine was conducted in France. Because it exhibited potent stimulating properties, the initial pharmacological research focused on ibogaine’s neuropharmacological effects. Only later were the hallucinogenic effects more precisely studied (Sanchez-Ramos and Mash 1996, 357).
In the 1960s, the Chilean psychiatrist Claudio Naranjo introduced ibogaine into psychotherapy as a “fantasy-enhancing drug” (Naranjo 1969*). One subject provided the following account of a shamanic experience during a psychotherapeutic session with the “stomach drug” ibogaine:
I am a panther! A black panther! I defend myself, I stand up. I snort powerfully, with the breath of a panther, predator breath! I move like a panther, my eyes are those of a panther, I see my whiskers. I roar, and I bite. I react like a panther, offense is the best defense.
Now I hear drums. I dance. My joints are gears, hinges, hubs. I can be a knee, a bolt, could do something, indeed almost anything. And I can loose [sic] myself again in this chaos of nonexistence and the perception of vague, abstract ideas of changing forms, where there exists a sense of the truth of all things and an order that one should set out to discover. (Naranjo 1979, 188*)
In Europe, the Swiss psychiatrist Peter Baumann provided the main impetus for the use of ibogaine in psychotherapy:
Baumann reported about experiments with completely synthetic ibogaine, which he used on only a few patients with whom a long and positive therapeutic relationship existed. The dosage was usually 5 mg/kg of body weight. At this dosage level, the effects lasted for approximately 5 to 8 hours and diminished only very slowly. In his experiments with ibogaine, the author found that it was not the substance as such that triggered a specific effect but that it induced an unspecific psychological and physical stimulus that was then responded to in the language that patient was accustomed to using with this therapist. (Leuner and Schlichting 1986, 162)
Unfortunately, an accident led to this initially promising research being halted. Marina Prins (1988) subsequently compared Baumann’s results with those reported by Naranjo.
Today, ibogaine is in the spotlight of neuropharmacological research because it has been shown that this alkaloid can be used to reduce and cure the addictive behavior of people dependent on other drugs (heroine, cocaine) (Sanchez-Ramos and Mash 1996; cf. Maps 6 [2; 1996]: 4–6). For example, ibogaine has been found to suppress the motor activity that occurs during opiate withdrawal. It has been proposed that ibogaine, when
ingested by opiate addicts in a single high dosage, dramatically reduces withdrawal symptoms while simultaneously causing a trip that provides the patient with such deep insights into the personal causes of the addiction that a majority of the individuals who receive such therapy can live for months without relapse. However, it should be noted that several additional sessions may be necessary before a persistent stabilization occurs. (Naeher 1996, 12)
Experiments with primates have shown that ibogaine reduces opiate addiction and partially blocks withdrawal symptoms. Although the neuropharmacological mechanism behind these effects has not yet been discovered, Deborah Mash and her team in Miami (Mash 1993; Mash et al. 1995) are researching this question. Ibogaine has been demonstrated to interact with numerous different receptors, and it has been concluded that this breadth of interaction is the reason for ibogaine’s effectiveness in addiction therapy (Sweetman et al. 1995).
In the United States, the use of ibogaine to treat addiction has been patented as the clinical Lotsof procedure (Lotsof 1995). Whether this procedure will receive endorsement from the medical community remains to be seen (Touchette 1995). A novel about this facet of ibogaine (which incorporates such actual people as Howard Lotsof) was published in Slovenia (Knut 1994).
Ibogaine enjoys a reputation for being an exceptionally potent and stimulating aphrodisiac (Naranjo 1969*).502 The research to date has entirely neglected this aspect.
Another substance of pharmacological and therapeutic interest is noribogaine, which is chemically and pharmacologically very similar to Prozac (fluoxetine). In the United States, Prozac is one of the most frequently prescribed psycho-pharmaca for depression, and it is celebrated as the “happy drug” in the popular press (Kramer 1995; Rufer 1995*).
Dosage and Application
Two to four tablets containing up to 8 mg ibogaine per tablet may be given daily as a stimulant for states of exhaustion, debility, et cetera. Nausea, vomiting, and ataxia are possible side effects. When used for psychotherapeutic purposes (Baumann), dosages of 3 to 6 mg of ibogaine hydrochloride per kg of body weight were administered. For psychoactive purposes, dosages of around 200 mg are recommended (Prins 1988, 47).
Commercial Forms and Regulations
Ibogaine was formerly available as a medicine under the trade name Bogadin (Schneider and McArthur 1956). In the United States, ibogaine is considered a Schedule I drug and has been prohibited since 1970. However, ibogaine hydrochloride is marketed under the trade name Endabuse and can be used with the appropriate special permit. In Germany, ibogaine is not considered a narcotic under the guidelines of the narcotic laws and is therefore legal (Körner 1994, 1573*).
“We are assuming that ibogaine triggers a fractal time structure that resembles the architecture of the REM dream phase during sleep by activating certain amygdaloid–cortico-thalamic circuits in the brain stem.”
LECTURE AT THE ENTHEOBOTANY CONFERENCE (SAN FRANCISCO, 1996)
The Slovenian novel Iboga, by Amon Knut Jr., has as its subject the therapeutic effects of ibogaine for alcoholism, cocaine abuse, heroin addiction, and nicotine dependency. (Book cover; Maribor: Skupina Zrcalo Publishers, 1994)
See also the entries for Tabernaemontana spp., Tabernanthe iboga, Voacanga spp., and indole alkaloids.
Baumann, Peter. 1986. “Halluzinogen”-unterstützte Psychotherapie heute. Schweizerische Ärztezeitung 67 (47): 2202–5.
Dybowski, J., and E. Landrin. 1901. Sur l’iboga, sur ses propriétés excitantes, sa composition et sur l’alcaloïde nouveau qu’il renferme. Comptes Rendues 133:748.
Fromberg, Eric. 1996. Ibogaine. Pan 3:2–8. (Includes a very good bibliography.)
Knut, Amon Jr. 1994. Iboga. Maribor: Skupina Zrcalo. (Cf. Curare 18 (1; 1995): 245–46.)
Kramer, Peter D. 1995. Glück auf Rezept: Der unheimliche Erfolg der Glückspille Fluctin. Munich: Kösel.
Le Men-Olivier, L., B. Richards, and Jean Le Men. 1974. Alcaloïdes des graines du Pandaca retusa. Phytochemistry 13:280–81.
Lotsof, Howard S. 1995. Ibogaine in the treatment of chemical dependence disorders: Clinical perspectives. Maps 5 (3): 15–27.
Mash, Deborah C. 1995. Development of ibogaine as an anti-addictive drug: A progress report from the University of Miami School of Medicine. Maps 6 (1): 29–30.
Mash, Deborah C., Julie K. Staley, M. H. Baumann, R. B. Rothman, and W. L. Hearn. 1995. Identification of a primary metabolite of ibogaïne that targets serotonin transporters and elevates serotonin. Life Sciences 57 (3): 45–50.
Naeher, Karl. 1996. Ibogain: Eine Droge gegen Drogenahhängigkeit? Hanfblatt 3 (21): 12–15 (interview).
Prins, Marina. 1988. “Von Iboga zu Ibogain: Über eine vielseitige Droge Westafrikas und ihre Anwendung in der Psychotherapie.” Unpublished licentiate thesis, Zurich. (Very rich bibliography.)
Sanchez-Ramos, Juan R., and Deborah Mash. 1996. Pharmacotherapy of drug-dependence with ibogain. Jahrbuch für Transkulturelle Medizin und Psychotherapie 6 (1995): 353–67.
Schneider, J., and M. McArthur. 1956. Potentiation action of ibogain (BogadinTM) on morphin analgesia. Experimenta 8:323–24.
Sweetman, P. M., J. Lancaster, Adele Snowman, J. L. Collins, S. Perschke, C. Bauer, and J. Ferkany. 1995. Receptor binding profile suggests multiple mechanisms of action are responsible for ibogaine’s putative anti-addiction activity. Psychopharmacology 118:369–76.
Touchette, Nancy. 1995. Anti-addiction drug ibogain on trial. Nature Medicine 1 (4): 288–89.
α-amino (3-hydroxy-5-isoxazolyl)acetic acid, α-amino-2,3-dihydro-3-oxo-5-isoxazole-acetic acid, ibotenic acid, “pilzatropin,” prämuscimol
Empirical formula: C5H6O4N2
Substance type: amino acid
Ibotenic acid was first isolated in 1964 from the Japanese mushroom Amanita strobiliformis (Paul) Quél. The Japanese name for this mushroom is ibotengu-take (“warty tengu mushroom”), and ibotenic acid was named after it (Ott 1993, 341*; Takemoto et al. 1964). Ibotenic acid is also found in Amanita muscaria and Amanita pantherina (Eugster et al. 1965). It may also be present in members of the genus Botelus (porcini mushrooms).
Ibotenic acid is structurally related to the neurotransmitter glutamate and may behave similarly in the nervous system. A psychoactive dose is regarded as 50 to 100 mg. Ibotenic acid is converted intomuscimol when stored (Good et al. 1965).
A traditional mask of tengu, the Japanese fly agaric mushroom spirits. Ibotenic acid was named after these spirits and their mushroom.
Commercial Forms and Regulations
Ibotenic acid is available from chemical suppliers and is a legal substance (Ott 1993, 440*).
See also the entries for Amanita muscaria, Amanita pantherina, and muscimol.
Eugster, C. H., G. F. R. Müller, and R. Good. 1965. Wirkstoffe aus Amanita muscaria: Ibotensäure und Muscazon. Tetrahedron Letters 23:1813–15.
Gagneux, A. R., et al. 1965. Synthesis of ibotenic acid. Tetrahedron Letters 965:2081–84.
Good, R., et al. 1965. Isolierung und Charakterisierung von Prämuscimol und Muscazon aus Amanita muscaria (L. ex Fr.) Hooker. Helvetica Chimica Acta 48 (4): 927–30.
Romagnesi, M. H. 1964. Champignons toxiques au Japon. Bulletin de la Société Mycologique de France 80 (1): iv–v.
Takemoto, T., T. Nakajima, and R. Sakuma. 1964. Structure of ibotenic acid. Yakugaku Zasshi 84:1233.
Indolalkaloide, indolamine alkaloids, indole, indoles
Indole alkaloids are derived from the indole ring system and appear almost exclusively in the families Apocynaceae503 (Alchornea spp., Alstonia scholaris, Aspidosperma quebracho-blanco, Catharanthus roseus, Rauvolfia spp., Tabernaemontana spp., Tabernanthe iboga, Vinca spp., Voacanga spp.), Loganiaceae (Gelsemium sempervirens, Strychnos nux-vomica, Strychnos spp.), and Rubiaceae (Corynanthe spp., Mitragyna speciosa, Pausinystalia yohimba). Indole alkaloids also occur in certain ascomycetes (Balansia cyperii, Claviceps paspali, Claviceps purpurea, Claviceps spp.), other fungi (Tyler 1961), and several climbing vines (Ipomoea violacea, Turbina corymbosa) (Hofmann 1966; cf. ergot alkaloids).
Included among the large group of indole alkaloids (Trojánek and Blaha 1966) are the β-carbo-lines with harmaline and harmine; the tryptamine derivates bufotenine, N,N-DMT, 5-MeO-DMT, psilocybin, and psilocin; the ergot alkaloids; and the alkaloids of the ibogane type (ibogaine, voacangine), yohimbane type (yohimbine), and strychnane type (strychnine). Indoles are also found in the genus Uncaria, several species of which are used as ayahuasca additives (Phillipson and Hemingway 1973).
Many indole alkaloids are psychoactive or occur in plants that are utilized for traditional psychoactive purposes (Lindgren 1995; Rivier and Pilet 1971; Schultes 1976).
See also the entries for β-carbolines, ergot alkaloids, and yohimbine.
Gershon, S., and W. J. Lang. 1962. A psychopharmacological study of some indole alkaloids. Archives Internationales de Pharmacodynamie et de Thérapie 135 (1–2): 31–56.
Hesse, M. 1968. Indolalkaloide in Tabellen. Berlin: Springer.
Hofmann, Albert. 1966. Alcaloïdes indoliques isolés de plantes hallucinogènes et narcotiques du Mexique. In Colloques internationaux du Centre National de la Recherche Scientifique: Phytochimie et plantes médicinales des terres du Pacifique, Noméa (Nouvelle Calédonie) 28.4–5.5.1964, 223–41. Paris: Centre National de la Recherche Scientifique.
Lindgren, Jan-Erik. 1995. Amazonian psychoactive indols: A review. In Ethnobothany: Evolution of a discipline, ed. Richard Evans Schultes and Siri von Reis, 343–48. Portland, Ore.: Dioscorides Press.
Phillipson, John David, and Sarah Rose Hemingway. 1973. Indole and oxindol alkaloids from Uncaria bernaysia. Phytochemistry 12:1481–87.
Rivier, Laurent, and Paul-Emile Pilet. 1971. Composés hallucinogènes indoliques naturels. Année Biol. 3:129–49.
Schultes, Richard Evans. 1976. Indole alkaloids in plant hallucinogens. Journal of Psychedelic Drugs 80 (1): 7–25.
Trojánek, J., and K. Bláha. 1966. A proposal for the nomenclature of indole alkaloids. Lloydia 29 (3): 149–55.
Tyler, Varro E. 1961. Indole derivatives in certain North American mushrooms. Lloydia 24:71–74.
Mescalin, meskalin, mezcalin, mezkalin, 3,4,5-trimethoxy-benzolmethanamine, 3,4,5-trimethoxy-β-phenethylamine, 3,4,5-trimethoxyethyl- phenylamine, TMPFA, 2-(3,4,5-trimethoxy-phenyl)-ethylamine
Empirical formula: C11H17NO3
Substance type: lophophora alkaloid, β-phenethylamine
Mescaline was first isolated in 1886 from “mescal buttons,” the aboveground parts of the peyote cactus (Lophophora williamsii), and was named after them. Mescaline is the most thoroughly studied of all psychoactive plant constituents. In the period between 1886 and 1950, more than one hundred mescaline research studies were published in the German language alone (Passie 1994). This alkaloid was found to be a component of numerous cacti (see the table on page 847). And it is possible that mescaline is produced from dopamine in vitro (Paul et al. 1969; Rosenberg et al. 1969).
Arthur Heffter was the first person to initially test an isolated plant constituent on himself (Heffter 1894). The classic Heffter dosage consisted of 150 mg mescaline hydrochloride (HCL). A psychedelic dosage is now considered to be 178 to 256 mg of mescaline HCL or 200 to 400 mg of mescaline sulfate. The highest measured dosage reported in the literature was 1,500 mg. Taken orally, 5 mg/kg of pure mescaline is regarded as a hallucinogenic dosage. In the toxicological literature, there is no known lethal dosage of mescaline when it is ingested orally (Brown and Malone 1978, 14).
Western psychiatry has been aware of consciousness-altering drugs since the nineteenth century. Mescaline was the first substance to be tested and applied in psychiatry. At the time, researchers regarded the effects of mescaline on a healthy subject as inducing a state that was otherwise known only in psychopathic patients. This led to the idea of pharmacologically induced “model psychoses” (Leuner 1962*). The effects of mescaline (and also of psilocybin) were described as “intoxication, toxic ecstasy, clouding of consciousness, hallucinosis, model psychosis, drug intoxication, emphasis, daydream,” et cetera (Passie 1994). Only in recent years has there been a shift in thinking away from the model psychosis concept and a recognition that psychedelic states and psychoses do not have a common origin (Hermle et al. 1988*, 1992*, 1993*).
The predominant effects of mescaline are a “reveling of the individual senses and primarily visual orgies” (Ellis 1971, 21). The mescaline inebriation was first systematically described by Kurt Beringer in 1927. To date, there have been many encounters with the substance, and the most commonly reported experiences are ecstatic and visionary in nature:
My awareness of subject and object disappeared, and I felt dissolved, rising in an orchestra of sounds. This ecstatic state was accompanied by an indescribable sensation of happiness. (Ammon and Götte 1971, 32)
It has often been suggested that pure mescaline can be taken in place of Lophophora williamsii. “However, most peyote users are of the opinion that synthetic mescaline cannot be compared with the effects of peyote” (Harp 1996, 16).
On the Cultural History of Mescaline
Aldous Huxley (1894–1963) made the psychedelic effects of mescaline famous in his two essays “The Doors of Perception” and “Heaven and Hell.”
Usually the person taking mescaline will discover an inner world that is so obviously something given, so enlighteningly eternal and sacred, as the transformed outer world that I had perceived with my eyes open. (Huxley 1970, 32*)
It is very likely that Hermann Hesse also had contact with mescaline, and that it may have inspired his novel Steppenwolf, one of the cult books of the hippie generation. The psychedelic rock band Steppenwolf took its name from the book, and the novel also became a motion picture starring Max von Sydow (USA 1974).
Nationalgalerie, a German New Wave band, sings on its album Mescaline, “To be transformed by a trickster fairy. My lawyer advised me to take some mescaline” (Sony Records, 1995).
“Peyote is always on mescaline.
Humans are sometimes on mescaline.
But no peyote could stand to always be on human.
We are but a side-effect of god.”
GALAN O. SEID UNPUBLISHED POEM (CA. 1985)
“Mescaline is the final, ultimate cult that does away with every cult.”
GÜNTER WALLRAFF MESKALIN
The cover of a very rare publication by the author Günter Wallraff regarding his experiences with mescaline.
Opuntia cylindrica is found in the Atacama Desert (northern Chile). It is easily identifiable by its very long, reddish thorns. The cactus contains mescaline, and the former inhabitants of oases in the region may have once used it for psychoactive purposes.
Cacti Containing Mescaline
(from Doetsch et al. 1980; La Barre 1979; Mata and McLaughlin 1982*; Shulgin 1995*; Lundström 1971; Pardanini et al. 1978; Ott 1993*; Turner and Heyman 1960)
Some species from the genus Gymnocalycium have been found to contain mescaline.
Although mescaline has been detected in some members of the genus Opuntia, no traditional use of these plants as psychoactive substances is known.
The French novelist and artist Henri Michaux (1899–1984) studied mescaline during the 1960s and ingested it to see what effects it might have upon his creativity. Like many other Frenchmen, however, he summarized his experience as an “accursed miracle” and scribbled his experiences of inner turmoil on paper (Michaux 1986). Today, these “drawings” are still reproduced in publications as an example of the “psychosis-like” effects of mescaline.
Commercial Forms and Regulations
Mescaline is available primarily as a hydrochloride or sulfate. In Germany, it is considered a “narcotic in which trafficking is prohibited.” In the United States, the Controlled Substances Act lists mescaline as a Schedule I substance (Körner 1994, 38*).
Many species of the Mexican prickly pear (Opuntia spp.) contain mescaline and other phenethylamines. To date, we know of no Opuntia that was used traditionally as an entheogen. (Woodcut from Tabernaemontanus, Neu Vollkommen Kräuter-Buch, 1731)
See also the entries for Lophophora williamsii, Trichocereus pachanoi, Trichocereus spp., and βphenethylamines.
Ammon, Günter, and Jürgen Götte. 1971. Ergebnisse früher Meskalin-Forschung. In Bewußtseinserweiternde Drogen aus psychoanalytischer Sicht, special issue, Dynamische Psychiatrie, 23–45.
Beringer, Kurt. 1927. Der Meskalinrausch. Berlin: Springer. Repr. 1969.
Blofeld, John. 1966. A high yogic experience achieved with meskalin. Psychedelic Review 7:27–32.
Doetsch, P. W., J. M. Cassidy, and J. L. McLaughlin. 1980. Cactus alkaloids. XL: Identification of mescaline and other phenethylamines in Pereskia, Pereskiopsis and Islaya by use of fluorescamine conjugates. Journal of Chromotography 189:79.
Ellis, Havelock. 1971. Zum Phänomen der Meskalin-Intoxikation, Bemerkungen zum Problem der Meskalin-Intoxikation. In Bewußtseinserweiternde Drogen aus psychoanalytischer Sicht, special issue, Dynamische Psychiatrie, 17–22.
Frederking, W. 1954. Meskalin in der Psychotherapie. Medizinischer Monatsspiegel, 3:5–7.
Harf, Jürgen C. 1996. Meskalin und Peyote. Grow! 6/96:15–16.
Heffter, Arthur. 1894. Über zwei Kakteenalkaloide. Berichte der deutschen Chemischen Gesellschaft 27:2975.
Klüver, Heinrich. 1926. Mescal vision and eidetic vision. American Journal of Psychology 37:502–15.
———. 1969. Mescal and mechanisms of hallucinations. Chicago: The University of Chicago Press.
La Barre, Weston. 1979. Peyotl and mescaline. Journal of Psychedelic Drugs 11 (1–2): 33–39.
Lundström, Jan. 1971. Biosynthetic studies on mescaline and related cactus alkaloids. Acta Pharm. Suecica 8:275–302.
Michaux, Henri. 1986. Unseliges Wunder: Das Meskalin. Munich and Vienna: Carl Hanser.
Pardanani, J. H., B. N. Meyer, and J. L. McLaughlin. 1978. Cactus alkaloids. XXXVII. Mescaline and related compounds from Opuntia spinosior. Lloydia 41 (3): 286–88.
Passie, Torsten. 1994. Ausrichtungen, Methoden und Ergebnisse früher Meskalinforschungen im deutschsprachigen Raum (bis 1950). In Jahrbuch des Europäischen Collegiums für Bewußtseinsstudien (1993/1994), 103–11. Berlin: VWB.
Paul., A.G., H. Rosenberg, and K. L. Khanna. 1969. The roles of 3,4,5-trihydroxy-β-phenethylamine and 3,4-dimethoxy-β-phenethylamine in their biosynthesis of mescaline. Lloydia 32 (1): 36–39.
Rosenberg, H., K. L. Khanna, M. Takido, and A. G. Paul. 1969. The biosynthesis of mescaline in Lophophora williamsii. Lloydia 32 (3): 334–38.
Turner, W. J., and J. J. Heyman. 1960. The presence of mescaline in Opuntia cylindrica. Journal of Organic Chemistry 25:2250.
Wallraff, Günter. 1968. Meskalin—Ein Selbstversuch. Berlin: Verlag Peter-Paul Zahl.
4,5α-epoxy-17-methyl-7-morphinen-3,6α-diol, morfina, morphin, morphinium, morphium
Empirical formula: C17H19NO3
Substance type: opium alkaloid
Sometime around 1803 and 1804, Friedrich Wilhelm Adam Sertürner (1783–1841), a pharmacist’s assistant, first isolated morphine as the “sleep-inducing principle” in opium (cf. Papaver somniferum, opium alkaloids). This achievement was the most important “quantum leap” in the history of pharmacology and represents the beginning of the true chemical investigation of plants. Today, the Sertürner Medal is still awarded for exceptional work in pharmaceutics.
Morphine may also be present in Papaver decaisnei Hochst., Papaver dubium L. [syn. Papaver modestum Jordan, Papaver obtusifolium Desf.], and Papaver hybridum L. (Slavík and Slavíková 1980). Whether morphine occurs in Argemone mexicana and other Papaver species (Papaver spp.) is doubtful, while the idea that hops (Humulus lupulus) contains morphine is a figment of someone’s imagination. Tiny traces of the substance have been found in hay and lettuce (cf. Lactuca virosa) (Amann and Zenk 1996, 19). Morphine has also been detected in the skin of Bufo marinus toads (cf. bufotenine) (Amann and Zenk 1996, 18).
“Morphine is to opium as alcohol is to wine.”
JEAN-MARIE PELT PFLANZENMEDIZIN [PLANT MEDICINE]
Since the time when morphine was first detected in breast milk, cow’s milk, and human cerebrospinal fluid, it has been known that it is a natural endogenous neurotransmitter in higher vertebrates, including humans (Amann and Zenk 1996; Cardinale et al. 1987; Hazum et al. 1981). Morphine does not bind well to the encephalin receptors (to which the endorphins dock) but docks at the specific morphine (m) receptors (Hazum et al. 1981). It is most likely biosynthesized in the body from dopamine (Brossi 1991). Another closely related substance, codeine, is also endogenous in humans (Cardinale et al. 1987).
Morphine is the best and strongest natural painkiller known. Its efficaciousness is surpassed only by that of the synthetic morphine analogs (heroin, fentanyl). Morphine is particularly well suited for treating chronic pain, such as in cancer therapy (Amann and Zenk 1996; Melzack 1991). Endogenous morphine constitutes the body’s own pain medication:
Studies on rats have shown that among animals who were suffering from arthritis, morphine concentrations in the spinal cord and urine were significantly elevated. Because of this, it is assumed today that the organism produces increased amounts of morphine in certain disease states. Consequently, endogenous morphine may serve to regulate pain in the organism. Morphine exists in animal and human tissue and is excreted in significant amounts in the urine. (Amann and Zenk 1996, 24)
About 30 mg orally represents an effective dosage. Habitual morphine users may use as much as 1 g per day (Hirschfeld and Linsert 1930, 255*):
It is known that opium eaters experience a significant increase in sexual functions during the initial period of opium consumption. During opium inebriation, erotic images appear and may even include extraordinary sexual fantasies. . . . The effects of morphine are similar, where an increase in sexual excitability was observed following several weeks of taking 0.03 to 0.06 g per day. (Max Marcuse, 1923, Handwörterbuch der Sexual-wissenschaft[Handbook of Sexual Sciences])
When used for sedation, in anesthesia, and for calming and antispasmodic purposes, pharmaceutical preparations of morphine hydrochloride and atropine sulfate or morphine hydrochloride and scopolamine hydrobromide are used—the final reminders of the recipes for the former soporific sponges.
During the Golden Twenties, the use of morphine in Berlin society circles was depicted in numerous pictures and illustrations (e.g., by Paul Kamm) that appeared in magazines. These illustrations played a great role in creating the stereotype of the “Morphinist”(cf. Papaver somniferum), who also became the object of literary treatments (Bulgaka 1971; Mac From 1931). Even the life story of the man who first discovered the substance, Friedrich Wilhelm Sertürner, became the subject of a novel (Schumann-Ingolstadt n.d.). Heroin, a derivative of morphine, has also inspired a rich body of literature. One of the first of this was the novel Heroin, by Rudolf Brunngraber (1952*), which dealt with the role of heroin in Egypt during the Golden Twenties.
Morphine was and still is a popular inebriant in the music scene (particularly that of jazz and rock). “Sister Morphine,” a song by the Rolling Stones (Sticky Fingers, Virgin Records, 1971), is arguably the most famous hymn to the drug. Morphine, a crossover band that mixes elements of cool jazz and modern rock, took its name from the alkaloid, and one of its albums is titled Cure for Pain (Rykodisc, 1993).
Commercial Forms and Regulations
Morphine is available from pharmacies in the form of morphine hydrochloride. Although morphine is covered by narcotics laws, it can be obtained with a special prescription. In the United States, morphine is a Schedule II substance.
“Illusionary ecstasies travel down confused nerves,
nervous trembling moves through pale hands,
the lips, red as a poppy, narrow as a knife, foam,
As if sensing blood in cups of gold,
A fragrance of orchids in the room,
pale yellow, heavy azaleas,
An arm bends in crazed desire,
A mouth grimaces quietly,
A gasp presses from the narrow chest: Morphium!”
ED. GOLLAND BRESLAU
IN DER JUNGGESELLE [THE BACHELOR]
In the early twentieth century, morphine (also known as morphium) was used as a cure for alcoholism. (Advertisements from German magazines 1907/1908)
The discovery of morphine or morphium led to some of the most significant innovations in the history of pharmacology and neurophysiology. The discovery has been described many times, even in novels. (Book cover, no date; novelized version of the life of German researcher F. W. Sertürner)
The American jazz-rock fusion trio Morphine has the best “cure for pain”: one of their songs is called “Let’s Take a Trip Together.” (CD cover 1993, Rykodisc)
“Please, Sister Morphine, turn my nightmares into dreams.
Oh, can’t you see I’m fading fast
and that this shot will be my last . . .”
MICK JAGGER AND KEITH RICHARDS “SISTER MORPHINE”
(STICKY FINGERS, VIRGIN RECORDS, 1971)
See also the entries for Papaver somniferum and Papaver spp.
Amann, Tobias, and Meinhart H. Zenk. 1996. Endogenes Morphin: Schmerzmittelsynthese in Mensch und Tier. Deutsche Apotheker Zeitung 136 (7): 17–25. (Contains a very good bibliography.)
Brossi, Arnold. 1991. Mammalian alkaloids: Conversions of tetrahydroisoquinoline-1-carboxylic acid derived from dopamin. Planta Medica 57 suppl. (1): 93 ff.
Bulgaka, M. 1971. Morphium Erzählungen. Zurich: Arche Verlag.
Cardinale, George J., Josef Donnerer, A. Donald Finck, Joel D. Kantrowitz, Kazuhiro Oka, and Sydney Spector. 1987. Morphine and codeine are endogenous compounds of human cerebrospinal fluid. Life Sciences 40:301–6.
Fairbain, J. W., S. S. Handa, E. Gürkan, and J. D. Phillipson. 1978. In vitro conversion of morphine to its N-oxide in Papaver somniferum latex. Phytochemistry 172:261–62.
Ferres, H. 1926. Gefährliche Betäubungsmittel: Morphium und Kokain. In Bibliothek der Unterhaltung und des Wissens, 5:136–44. Stuttgart: Union Deutsche Verlagsgesellschaft.
Hazum, Eli, Julie J. Sabatka, Kwen-Jen Chang, David A. Brent, John W. A. Findlay, and Pedro Cuatrecasas. 1981. Morphine in cow and human milk: Could dietary morphine constitute a ligand for specific morphine (m) receptors? Science 213:1010–12.
Kramer, John C. 1980. The opiates: Two centuries of scientific study. Journal of Psychedelic Drugs 12 (2): 89–103.
Mac From, ed. 1931. Täglich 5 Gramm Morphium— Aufzeichnungen eines Morphinisten. Berlin-Pankow: A. H. Müller.
Melzack, Ronald. 1991. Morphium und schwere chronische Schmerzen. Offprint of Spektrum der Wissenschaft. Heidelberg: Spektrum der Wissenschaft Verlag.
Schmitz, Rudolf. 1983. Friedrich Wilhelm A. Sertürner und die Morphinentdeckung. Pharmazeutische Zeitung 128:1350–59.
Schuhmann-Ingolstadt, Otto. n.d. Morphium: Lebensroman des Entdeckers. Berlin and Frankfurt/M.: Deutscher Apothekerverlag.
Slavík. J., and L. Slavíková. 1976. Occurrence of morphin as a minor alkaloid in Papaver decaisnei Hochst. Collection Czechoslov. Chem. Commun. 45:2706–9.
Agarin, 5-(aminomethyl)-3-[2H]-isoxazolone, pyroibotenic acid, 3-hydroxy-5-aminomethyl-isoxazole
Empirical formula: C4H6O2N
Substance type: amino acid, isoxazole derivative
Muscimol was first described in 1964 as a constituent of Amanita pantherina. Muscimol is the decarboxylated product of ibotenic acid and is considered to be more psychoactive than it. Some 15 to 20 mg is regarded as a psychoactive dosage (Müller and Eugster 1965; Ott 1993, 446*; Scotti et al. 1969).
Muscimol is an analog of the neurotransmitter GABA (gamma amino butyric acid) and docks to its receptor (Johnston 1971). Kavapyrones (cf. Piper methysticum) also bind to the same receptor.
Ibotenic acid as well as muscimol were detected in the urine of people who had eaten fly agaric mushrooms (Amanita muscaria) about an hour earlier. An experiment with mice conducted by the same team of researchers found that the amount of active constituents in the urine passed by one inebriated animal was not sufficient to inebriate another animal (Ott et al. 1975).
Commercial Forms and Regulations
Muscimol can be purchased from chemical suppliers. The substance is legal and is not subject to any specific regulations.
The panther cap (Amanita pantherina) is found throughout Eurasia and North America. Its effects are similar to, but more pronounced than, those of the fly agaric. (Photograph: Paul Stamets)
See also the entries for Amanita muscaria and ibotenic acid.
Johnston, G. A. R. 1971. Muscimol and the uptake of γ-aminobutyric acid by rat brain slices. Psychopharmacologia 22:230.
Müller, G. F. R., and C. H. Eugster. 1965. Muscimol, ein pharmakodynamisch wirksamer Stoff aus Amanita muscaria. Helvetica Chemica Acta 48:910–26.
Ott, Jonathan, Preston S. Wheaton, and William Scott Chilton. 1975. Fate of muscimol in the mouse. Physiol. Chem. and Physics 7:381–84.
Scotti de Carolis, A., et al. 1969. Neuropharmacological investigations on muscimol, a psychotropic drug extracted from Amanita muscaria. Psychopharmacologia 15:186–95.
Nicotin, nikotin, (–)-nikotin , 1-methyl-2(3-pyridyl)-pyrrolidine, 3-(1-methyl-2-pyrrolidinyl)pyridine
Empirical formula: C10H14N2
Substance type: pyrrolidine alkaloid, pyridine alkaloid, tobacco alkaloid
Nicotine was first discovered in tobacco (Nicotiana tabacum) and was named for the genus. It occurs in numerous species of Nicotiana as well as other members of the Nightshade Family. It has also been found in club moss (Lycopodium clavatum).
Nicotine is very easily absorbed through the mucous membranes and even through the skin. Consequently, plants that contain nicotine can be smoked or administered as enemas. Nicotine is broken down through oxidation, and about 10% is excreted unchanged. It has stimulating effects upon the central nervous system and has paralyzing effects at very high dosages (cf. cytisine). In the peripheral nervous system, nicotine behaves in a similar manner as the neurotransmitter acetylcholine. High dosages can result in sudden death due to respiratory paralysis or cardiac arrest within five minutes of ingestion (Roth et al. 1994, 864*). From 40 to 60 mg represents a lethal dosage for humans (Frerichs, Arends, Zörnig, Hagers Handbuch). Diazepam can be effective as an antidote for nicotine poisoning (Roth et al. 1994, 865*). Nicotine is now generally regarded as highly “addictive” (Schiffman 1981). Although it is commonly assumed that nicotine causes cancer, uncertainty has been expressed about this theory (Schievelbein 1972).
Nicotine has been detected in Egyptian mummies (New Kingdom) (Balabanova et al. 1992*). However, this discovery should not be taken as evidence that the Egyptians knew of wild tobacco (Nicotiana rustica), as the Balabanova team in Munich has suggested, for some Old World plants also contain nicotine (see the table at right).
Commercial Forms and Regulations
Nicotine can be obtained in its pure form from chemical suppliers. It is subject to the laws covering the transport of dangerous substances and is classified as a Category 1 substance on the Swiss Poison List. In the United States, pure nicotine is available only with a prescription (Ott 1993, 447*). In Germany, it is subject to the laws regarding dangerous substances but is not regarded as a “narcotic.”
Plants Containing Nicotine
(from Bock 1994, 93*; Römpp 1995, 2995*; Schultes and Raffauf 1991, 37*; supplemented)
A smoking Indian inspects his tobacco plants. Native Americans cultivate tobacco strains with especially high nicotine contents.
See also the entries for Nicotiana rustica, Nicotiana tabacum, and Nicotiana spp.
Lee, Richard S., and Mary Price Lee. 1994. Caffeine and nicotine. New York: The Rosen Publishing Group.
Schievelbein, H. 1972. Biochemischer Wirkungsmechanismus des Nikotins oder seiner Abbauprodukte hinsichtlich eines eventuellen carcinogenen, mutagenen oder teratogenen Effektes. Planta Medica 22:293–305.
Shiffman, Saul. 1981. Tabakkonsum und Nikotinabhängigkeit. In Rausch und Realität, ed. G. Völger, 2:780–83. Cologne: Rautenstrauch-Joest-Museum für Völkerkunde.
Dimethyltryptamin, dimethyltryptamine, DMT, nigerin, nigerina, nigerine (1946), N,N-dimethyltryptamine, 3-[2-(dimethyl-amino)ethyl]-indole
Empirical formula: C12H16N2
Substance type: tryptamine (indole alkaloid)
R. H. F. Manske first created DMT as a synthetic substance in the laboratory in 1931. It was not until 1955 that it was isolated as a natural compound in the seeds of Anadenanthera peregrina. It is found in a great number of plants and also occurs naturally in humans and other mammals (see table, pages 853–854). N,N-DMT is closely related to 5-MeO-DMT and psilocybin/psilocin.
N,N-DMT and 5-MeO-DMT are among the psychedelics whose effects are short in duration. They are not orally effective in an isolated form (as a salt or a base) because the MAO enzyme breaks them down before they can pass through the blood–brain barrier (cf. ayahuasca, β-carbolines). They reveal their awesome effects only when injected by syringe (Strassman et al. 1994), snuffed, or smoked. When N,N-DMT or 5-MeODMT is injected intravenously, the effects last some forty-five minutes; when the substance is smoked or snuffed, the effects last only ten minutes. Subjectively, however, those few minutes may seem to have spanned centuries. People who have had experiences with DMT unanimously agree that it is easily the most powerful psychedelic known (cf. McKenna 1992; Meyer 1992). Some people have described DMT as “crystallized consciousness.” When DMT is smoked, it is said that the “scent of enlightenment” fills the air. Only “a few seconds after taking it, DMT acts like the trumpets of Jericho upon the gates of perception” (Kraemer 1995, 98). DMT experiences can be so extraordinarily alien that most subjects find it extremely difficult or even impossible to describe them in words. Many people speak of contact with strange beings (aliens, fairies, machine elves, et cetera) (Bigwood and Ott 1977; Leary 1966; McKenna 1992; Meyer 1992).
When pure DMT is smoked or vaporized and inhaled, the effective dosage lies around 20 mg (although amounts as high as 100 mg are sometimes smoked). The dosage for ayahuasca and ayahuasca analogs ranges from 50 to 100 mg. When DMT is injected, the typical dose is 1 mg/kg of body weight (Ott 1993, 433*).
DMT is also produced in the human nervous system, where it appears to serve an important function as a neurotransmitter (Barker et al. 1981; Callaway 1996; Siegel 1995b). Neurobiologists are as yet uncertain about the role DMT might play in the nervous system. Hyperventilating causes the concentration of DMT in the lungs to increase (Callaway 1996). One physician has reported that the release of endogenous DMT is highest at the moment of death. It is my opinion that this chemical messenger is responsible for the ultimate shamanistic ecstasy, for enlightenment, and for the merging into the “clear light of death.” An experiment in which DMT was given to practicing Buddhists found that the subjects had experiences and visions that corresponded to the Buddhist teachings (Strassman 1996).
DMT has clearly inspired numerous novels in the fantasy and science-fiction genres. The novel Kalimantan deals with the search for a fictitious hallucinogenic drug called seribu aso. The descriptions of the effects of this drug agree perfectly with the descriptions of DMT trips (Shepard 1993). Several novels, including the Valis trilogy of the science-fiction master Philip K. Dick (1928–1982), also appear to represent a literary attempt to understand the hyperdimensionality of DMT experiences (Dick 1981a, 1981b, 1982).
Commercial Forms and Regulations
DMT occurs as a free base, an HCL, and a fumarate. Although the fumarate crystallizes out easily, it contains only 60% of the pure substance. DMT is classified as a Schedule I drug in the United States and is a “narcotic drug in which trafficking is not allowed” in Germany as well as in Switzerland (Körner 1994, 38*).
“DMT is everywhere!”
DR. ALEXANDER T. SHULGIN
ASK DR. SHULGIN ONLINE DRUG INFORMATION WEB SITE OF THE CENTER FOR COGNITIVE LIBERTY AND ETHICS
“DMT is the Tyrannosaurus rex of psychedelics.”
“DMT trips are some of the most intense drug experiences in the world and only the fact that they last a short time makes them tolerable. . . . Every human brain also normally contains DMT. Why? What is such a strong drug doing there? Why does stress increase the amount of DMT, which is then released into the cerebrospinal fluid—the fluid that surrounds the spinal cord?”
RONALD SIEGEL HALLUZINATIONEN [HALLUCINATIONS] (1995B, 401*)
The seeds of the Leguminosae Desmodium tiliaefolium contain detectable amounts of N,N-DMT and bufotenine.
Plants Containing DMT
(from Block 1994*; Smith 1977; Montgomery, pers. comm.; Ott 1993*; Schultes and Hofman 1980, 155*; supplemented)
DMT has been detected in several species of Desmodium. (From Hernández, 1942/46 [Orig. pub. 1615]*)
“The first puff immediately took me into a completely different reality, a reality immanent to the normal one but surpassing it by leaps and bounds. Dripping and pearling off my companions were blue and violet dabs of color that extended and flowed together through the room. The small drops were overlapping and pushing into each other, arranging themselves into the most magnificent patterns and forming a circle.
“When the room had become a cathedral of dancing patterns, rays of light shot through the room, jumping from one person to the next. A glowing ring of bodiless consciousness and high-caliber energy shot through the circle. The chakras were blooming. I was able to see and feel them clearly. The kundalini energy shot to the top and sprayed from the heads, to join together with the eternity of that which can be experienced. I sensed the power of the ring and was initiated into an ancient cult. The person across from me looked like a priest from an earlier culture.
“The bustling activity of the patterns of magnificent color and thousandfold patterns became wilder and ever more intense. I was able to perceive absolutely the same things whether I kept my eyes open or closed. The flying lights and swinging colors became pure light that condensed into cosmic laughter. A tryptamine initiation.”
A DMT EXPERIENCE
See also the entries for 5-MeO-DMT.
Arnold, O. H., and G. Hofman. 1957. Zur Psychopathologie des Dimethyltryptamine. Wiener Zeitschrift für Nervenheilkunde 13:438–45.
Barker, S., J. Monti, and S. Christian. 1981. N,N-dimethyltryptamine: An endogenous hallucinogen. International Review of Neurobiology 22:83–110.
Bigwood, Jeremy, and Jonathan Ott. 1977. DMT: The fifteen minute trip. Head 11:56 ff.
Callaway, James. 1996. DMTs in the human brain. In Yearbook for Ethnomedicine and the Study of Consciousness (1995), 4:45–54. Berlin: VWB.
Dick, Philip K. 1981a. The divine invasion, New York: Vintage Books.
———. 1981b. Valis. New York: Vintage Books.
———. 1982. The transmigration of Timothy Archer. New York: Vintage Books.
Kraemer, Olaf. 1995. Die Trompeten Jerichos. Wiener 9:97–99.
Lamparter, Daniel, and Adolf Dittrich. 1996. Intraindividuelle Stabilität von ABZ unter sensorischer Deprivation, N,N-Dimethyltryptamin (DMT) und Stickoxydul. In Jahrbuch des Europäischen Collegiums für Bewußtseinsforschung (1995), 33–43. Berlin: VWB.
Leary, Timothy. 1966. Programmed communication during experience with DMT. Psychedelic Review 8:83–95.
Manske, R. H. F. 1931. A synthesis of the methyltryptamines and some derivatives. Canadian Journal of Research 5:592–600.
McKenna, Terence. 1992. Tryptamin hallucinogens and consciousness. In Yearbook for Ethnomedicine and the Study of Consciousness (1992), 1:133–48. Berlin: VWB.
Meyer, Peter. 1992. Apparent communication with discarnate entities induced by dimethyltryptamine DMT. In Yearbook for Ethnomedicine and the Study of Consciousness (1992), 1:149–74. Berlin: VWB.
Shepard, Lucius. 1993. Kalimantan. New York: Tom Doherty Associates.
Shulgin, Alexander T. 1976. Profiles of psychedelic drugs. 1: DMT. Journal of Psychedelic Drugs 8 (2): 167–68.
Smith, Terence A. 1977. Tryptamine and related compounds in plants. Phytochemistry 16:171–75.
Strassman, Rick J. 1996. Sitting for sessions: Dharma and DMT research. Tricycle 6 (1): 81–88.
Strassman, Rick J., Clifford R. Qualls, Eberhard H. Uhlenhuth, and Robert Kellner. 1994. Dose-response study of N,N-dimethyltryptamin in humans. Archive of General Psychiatry 51:85–97, 98–108.
Szára, S. I. 1956. Dimethyltryptamin: Its metabolism in man; the relation of its psychotic effect to the serotonin metabolism. Experientia 15 (6): 441–42.
Opiate, opiates, opium compounds
The study of opium and the isolation of its constituents ranks among the most important achievements in the history of pharmacology (cf. Papaver somniferum). In ancient times, opium was already known as the best of all analgesics (cf. soporific sponge). The isolation of morphine from opium revolutionized pain therapy in Europe. No other component of opium has a comparably powerful effect. The potency of morphine would not be exceeded until heroin (diacetylmorphine) was synthesized (Snyder 1989). Subsequent pharmacological research has led to the creation of numerous morphine analogs (fentanyls), some of which are as much as 7,500 times more potent than morphine (Sahihi 1995, 31ff.*).
The opium alkaloids codeine and morphine have become culturally significant as psychoactive substances. Papaverine is used in medicine as a treatment for impotence.
Some opium alkaloids are also found in other Papaver species (Papaver spp.), although these species usually contain only traces of these substances (Khanna and Sharma 1977; Küppers et al. 1976; Phillipson et al. 1973; Phillipson et al. 1976).
Aporphines, whose structures are analogous to those of the opium alkaloids, occur in Papaver fugax Poir. [syn. Papaver caucasicum M.-B., Papaver floribundum Desf.] and Nymphaea ampla. Other substances related to the opium alkaloids are present in Argemone mexicana, Eschscholzia californica, Nuphar lutea, and Papaver spp.
“The hall of wonder drugs [at the German Museum in Munich] is huge, a curious demonstration of German pharmacology. Morphine, methamphetamine, adolphine (a synthetic heroin named after Hitler), etc. Every drug on display comes with a complete little biography of its own. The little sign next to methamphetamine says that it was given to Stuka pilots in World War II and that soldiers at the eastern front took it in order to stay awake. And that it was Hitler’s favorite drug. We learn about the various nicknames: ‘coffee substitute,’‘lightning powder,’ etc.”
AN AMERICAN ODYSSEY (1996, 15 f.)
The most powerful tool of the American heavy metal band Tool is a strong Opiate (CD cover 1992, BMG Music)
The Constituents of Opium
The composition of the alkaloid mixture can vary greatly, depending upon the strain of poppy, the location of cultivation, and the processing technique (Krikorian and Ledbetter 1975).
See also the entries for Argemone mexicana, Papaver somniferum, Papaver spp., codeine, morphine, and papaverine.
Khanna, P., and G. L. Sharma. 1977. Production of opium alkaloids from in vitro tissue culture of Papaver rhoeas L. Indian Journal of Experimental Biology 15:951–52.
Krikorian, A. D., and M. C. Ledbetter. 1975. Some observations on the cultivation of opium poppy (Papaver somniferum L.) for its latex. Botanical Review 41:30–103.
Küppers, F. J. E. M., C. A. Salmink, M. Bastart, and M. Paris. 1976. Alkaloids of Papaver bracteatum: Presence of codeine, neopine and alpinine. Phytochemistry 15:444–45.
Phillipson, J. D., S. S. Handa, and S. W. El-Dabbas. 1976. N-oxides of morphine, codeine and thebaine and their occurrence in Papaver species. Phytochemistry 15:1297–1301.
Phillipson, J. D., G. Sariyar, and T. Baytop. 1973. Alkaloids from Papaver fugax of Turkish origin. Phytochemistry 12:2431–34.
Scully, Rock, with David Dalton. 1996. An American odyssey: Die legendäre Reise von Jerry Garcia und den Grateful Dead. St.Andrä-Wördern: Hannibal Verlag.
Snyder, Solomon H. 1989. Brainstorming: The science and politics of opiate research. Cambridge and London: Harvard University Press.
1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisochino-line, papaverin, papaverina, papavérine
Empirical formula: C20H21NO4
Substance type: opium alkaloid
Papaverine is a component of opium (0.3 to 0.8%) and was named after the genus Papaver (cf. Papaver somniferum). Papaverine has very weak psychoactive properties but is a powerful vasodilator. Effective dosages start at 200 mg. An extract of Nuphar lutea has similar effects.
In recent years, papaverine has been used to treat impotence, often with good success (Mellinger et al. 1987). When used for this purpose, the substance is injected directly into the corpus cavernosum when the penis is flaccid (so-called SKAT therapy; cf. Ernst et al. 1993). Among the problems that this method may cause are painful priapism (persistent erections for up to thirty-six hours without sexual arousal!) and inflammation of the penis (Sanders 1985).
Commercial Forms and Regulations
The substance, available as papaverine hydrochloride, is sold in suppository form and in solution for injection. Papaverine is available only with a prescription.
Papaverine, an active constituent isolated from opium, is prescribed for impotence and is injected into the penis.
See also the entries for Papaver somniferum and opium alkaloids.
Ernst, Günter, Hans Finck, and Dieter Weinert. 1993. Dem Manne kann geholfen werden. Munich: Ehrenwirth.
Mellinger, Brett C., E. Darracott Vaughan, Stephen L. Thompson, and Marc Goldstein. 1987. Correlation between intracavernous papaverine injection and Doppler analysis in impotent men. Urology 30 (5): 416–19.
Porst, H. 1996. Orale und intracavernöse Pharmakotherapie. TW Urologie Nephrologie 8 (2): 88–94.
Sanders, Kevin. 1985. 30-Stunden Erektion. Penthouse 4/85:65–68, 196, 200.
Schnyder von Wartensee, M., A. Sieber, and U. E. Studer. 1988. Therapie der erektilen Dysfunktion mit Papaverin—21/2 Jahre Erfahrung. Schweizer medizinische Wochenschrift 118 (30): 1099–1103.
Psilocybin: CY-39, indocybin, O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine, 3(2-dimethyl-amino)ethylindol-4-ol dihydrogenphosphatester
Psilocin: 4-hydroxy-N,N-dimethyltryptamine, psilocine, psilocyn (misspelling in the legal literature), 3-[2-(dimethylamino)ethyl]-1H—indole-4-ol
Empirical formula: C12H17N2O4P (psilocybin), C12H16N2O (psilocin)
Substance type: tryptamines, indole amines (indole alkaloids)
Psilocybin was first isolated from Psilocybe mexicana and identified by Albert Hofmann in 1955 (Hofmann et al. 1958, 1959). The phosphorylated indole amine psilocybin is transformed into psilocin by splitting off the phosphoric acid group (Hofmann and Troxler 1959). Because the protection the phosphoric acid would provide is lacking, psilocin easily oxidizes with the phenolic hydroxyl group, resulting in blue quinonoid products. This explains why psilocybin mushrooms turn blue after they have been squeezed and harvested (cf. Panaeolus cyanescens, Psilocybe cyanescens). In the body, psilocybin is immediately metabolized into psilocin, which is the actual psychoactive constituent.
Psilocybin and psilocin are closely related to baeocystin (= O-phosphoryl-4-hydroxy-N-methyltryptamine, norpsilocybin), which probably represents the biogenic precursor of psilocybin (Repke et al. 1977; cf. also Brack et al. 1961 and Chilton et al. 1979). Baeocystin may be a derivative of tryptophan (Brack et al. 1961).
The usual psychedelic dosage of psilocybin is 10 mg. When psilocybin is taken orally, the effects typically become apparent in about twenty minutes506 (Shulgin 1980). Rudolf Gelpke (1928– 1972) took between 6 and 20 mg during his self-experiments; with 10 mg, he made his historic “journey to the outer space of the soul”:
This inebriation was a space flight not into the outer realm, but into the inner person, and for a moment I experienced reality from a position located somewhere beyond the gravity of time. (Gelpke 1962, 395)
With very high dosages, it is common to perceive voices (Beach 1997). This could explain why Indians say that the mushroom talks to them. Toxic dosages are unknown!
Walter Pahnke’s “Good Friday experiment,” in which theology students were administered psilocybin in a church on Good Friday, has become renowned. Pahnke applied the theory of dosage, set, and setting as part of the test to see whether mystical revelations would occur, which was indeed the case (Pahnke 1972; Pahnke and Richards 1970; cf. Doblin 1991).
Timothy Leary and his colleagues at Harvard experimented with psilocybin on prisoners. Their experiments were aimed at determining whether the psychedelic constituent was suitable for use in therapy with inmates. It was hoped that the drug experience would enable the prisoners to attain insights into their behavior that would then enable them to change themselves on their own. Although these experiments showed great promise, they had to be terminated (Clark 1970; Forcier and Doblin 1994; Riedlinger and Leary 1994).
Both psilocybin and two synthetic derivatives (CZ-74, CY-19) have been used with success in psychedelic and psycholytic therapy (Leuner 1963; Leuner and Baer 1965; Passie 1995, 1996). Psilocybin can release, stimulate, and inspire creativity (Fischer et al. 1972), as an increasing number of studies have shown (Baggott 1997; Spitzer et al. 1996), and “archetypal art therapy” is making use of this effect (Allen 1995).
Today, psilocybin is playing a central role in neurochemical research into brain activity, in which it is being studied with the very elaborate and costly positron-emission tomography (PET) method (Vollenweider 1996).
Jochen Gartz has discovered that fungal enzymes synthesize the “synthetic” psilocin analog CZ-74 (diethyl-4-hydroxytryptamine, 4-OH-DET) from diethyltryptamine when it is added to a Psilocybe spp.substrate (J. Gartz, pers. comm.). It is possible that the “synthetic” CY-19 (= diethyl-4-phosphoryloxytryptramine) can be produced in the same fashion.
Commercial Forms and Regulations
Both psilocybin and psilocin are classified as Schedule I drugs in the United States (Shulgin 1980). They are internationally regarded as illegal “narcotics.” The analog substances psilocin-(eth) and psilocybin-(eth) are also illegal (Körner 1994, 40*).
Microscopic views of psilocybin and psilocin, the active constituents in mushrooms, after crystallization from methanol. (Photograph: Albert Hofmann)
The structural formulas of the two active mushroom constituents psilocybin and psilocin, shown here in the handwriting of their discoverer, Albert Hofmann.
“The chemical structures of psilocybin and psilocin were new and important in a number of ways. These two mushroom constituents were the first naturally occurring indole compounds with a hydroxyl function in the 4th position of the indole system. Psilocybin is the only known indole alkaloid [apart from its analog baeocystin] in which there is a substituted phosphoryloxy group. The chemical relationship between psilocin and the neurotransmitter serotonin is of particular importance.”
“PILZLICHE HALLUZINOGENE” [“FUNGAL HALLUCINOGENS”]
(DER CHAMPIGNON, JUNE 1987, P. 24)
See also the entries for Psilocybe mexicana and Psilocybe spp.
Allen, Tamara D. 1994. Research in archetypal art therapy with psilocybin. Maps 5 (1): 39–40.
———. 1995. Archetypal art therapy: Hearing psilocybin in the art & metaphor work of volunteer no. 31. Maps 6 (1): 23–26.
Baggot, Matthew. 1997. Psilocybin’s effects on cognition: Recent research and its implications for enhancing creativity. Maps 7 (1): 10–11.
Beach, Horace. 1997. Listening for the logos: Study of reports of audible voices at high doses of psilocybin. Maps 7 (1): 12–17.
Bocks, S. M. 1968. The metabolism of psilocin and psilocybin by fungal enzymes. Biochemical Journal 106:12–13.
Borner, Stefan, and Rudolf Brenneisen. 1987. Determination of tryptamines in hallucinogenic mushrooms using high-performance liquid chromatography with photodiode array detection. Journal of Chromatography 408:402–8.
Brack, A., Albert Hofmann. F. Kalberer, H. Kobel, and J. Rutschmann. 1961. Tryptophan als biogenetische Vorstufe des Psilocybins. Archiv der Pharmazie 294/66 (4): 230–34.
Chilton, W. Scott, Jeremy Bigwood, and Robert E. Jensen. 1979. Psilocin, bufotenine, and serotonin: Historical and biosynthetic observations. Journal of Psychedelic Drugs 11 (1–2): 61–69.
Clark, Jonathan. 1970. Psilocybin: The use of psilocybin in a prison. In Psychedelics, ed. Bernard Aaronson and Humphry Osmond, 40–44. Garden City, N.Y.: Anchor Books.
Doblin, Rick. 1991. Pahnke’s ‘Good Friday experiment’: A long-term follow-up and methodological critique. The Journal of Transpersonal Psychology 23 (1): 1–28.
Fischer, Roland, Ronald Fox, and Mary Ralstin. 1972. Creative performance and the hallucinogenic drug-induced creative experience. Journal of Psychedelic Drugs 5 (1): 29–36. (On psilocybin and creativity research.)
Forcier, Michael W., and Rick Doblin. 1994. Long-term follow-up to Leary’s Concord Prison psilocybin study. Maps 4 (4): 20–21.
Gelpke, Rudolf. 1962. Von Fahrten in den Weltraum der Seele: Berichte über Selbstversuche mit Delysid (LSD) und Psilocybin (CY). Antaios 3:393–411.
———. . Von Fahrten in den Weltraum der Seele: Berichte über Selbstversuche mit LSD und Psilocybin. Löhrbach: Werner Pieper’s MedienXperimente and Edition Rauschkunde.
Gnirss, Fritz. 1959. Untersuchung mit Psilocybin, einem Phantastikum aus dem mexikanischen Rauschpilz Psilocybe mexicana. Schweizer Archiv für Neurologie, Neurochirurgie und Psychiatrie 84:346–48.
Hofmann, Albert, A. Frey, H. Ott, Th. Petrzilka, and F. Troxler. 1958. Konstitutionsaufklärung und Synthese von Psilocybin. Experientia 14 (11): 397–401.
Hofmann, Albert, Roger Heim, A. Brack, and H. Kobel. 1958. Psilocybin, ein psychotroper Wirkstoff aus dem mexikanischen Rauschpilz Psilocybe mexicana Heim. Experientia 14 (3): 107–12.
Hofmann, Albert, Roger Heim, A. Brack, H. Kobel, A. Frey, H. Ott, T. Petrzilka, and F. Troxler. 1959. Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen. Helvetica Chimica Acta 42 (162): 1557–72.
Hofmann, Albert, and F. Troxler. 1959. Identifizierung von Psilocin. Experientia 15 (3): 101–4.
Jones, Richard. 1963. “Up” on Psilocybin. The Harvard Review 1 (4): 38–43.
Krippner, Stanley. 1970. Psilocybin: An adventure in psilocybin. In Psychedelics, ed. Bernard Aaronson and Humphry Osmond, 35–39, Garden City, N.Y.: Anchor Books.
Laatsch, Hartmut. 1994. Das Fleisch der Götter—Von den Rauschpilzen zur Neurotransmission. In Welten des Bewußtseins, ed. A. Dittrich et al., 3:181–95. Berlin: VWB.
———. 1996. Zur Pharmakologie von Psilocybin und Psilocin. In Maria Sabina—Botin der heiligen Pilze, ed. Roger Liggenstorfer and Christian Rätsch, 193–202. Solothurn: Nachtschatten Verlag.
Leuner, Hanscarl. 1963. Die Psycholytische Therapie: Klinische Psychotherapie mit Hilfe von LSD-25 und verwandten Substanzen. Zeitschrift für Psychotherapie und medizinische Psychologie 13:57 ff.
Leuner, Hanscarl, and G. Baer. 1965. Two short-acting hallucinogens of the psilocybin-group. In Neuro-pharmacology, ed. D. Bente and P. B. Bradley. Amsterdam: Elsevier.
Ott, Jonathan, and Gastón Guzmán. 1976. Detection of psilocybin in species of Psilocybe, Panaeolus and Psathyrella. Lloydia 39:258–60.
Pahnke, Walter N. 1972. Drogen und Mystik. In Josuttis and Leuner, 54–76*.
Pahnke, Walter N., and William A. Richards. 1970. Implications of LSD and experimental mysticism. Journal of Psychedelic Drugs 3 (1): 92–108.
Passie, Torsten. 1995. Psilocybin in der westlichen Psychotherapie. Curare 18 (1): 131–52.
———. 1996. Psilocybin in der westlichen Psychotherapie. In María Sabina—Botin der heiligen Pilze, ed. Roger Liggenstorfer and Christian Rätsch, 211–25. Solothurn: Nachtschatten Verlag.
Repke, David B., Dale Thomas Leslie, and Gastón Guzmán. 1977. Baeocystin in Psilocybe, Conocybe and Panaeolus. Lloydia 40 (6): 566–78.
Riedlinger, Thomas, and Timothy Leary. 1994. Strong medicine for prisoner reform: The Concord Prison experiments. Maps 4 (4): 22–25.
Shulgin, Alexander T. 1980. Psilocybin. Journal of Psychedelic Drugs 12 (1): 79.
Spitzer, M., M. Thimm, L. Hermle, P. Holzmann, K. A. Kovar, H. Heimann, E. Gouzoulis-Mayfrank, U. Kischka, and F. Schneider. 1996. Increased activation of indirect semantic associations under psilocybin. Biological Psychiatry 39:1055–57.
Strassmann, Rick. 1992. DMT and psilocybin research. Maps 3 (4): 8–9.
———. 1995. University of New Mexico DMT and psilocybin studies. Maps 5 (3): 14–15.
Troxler, F., F. Seemann, and Albert Hofmann. 1959. Abwandlungsprodukte von Psilocybin und Psilocin. Helvetica Chimica Acta 42 (226): 2073–103.
Vollenweider, Franz. 1996. Perspektiven der Bewußtseinsforschung mit Halluzinogenen. In Maria Sabina—Botin der heiligen Pilze, ed. Roger Liggenstorfer and Christian Rätsch, 203–10. Solothurn: Nachtschatten Verlag.
Empirical formula: C23H28C8
Substance type: diterpene (clerodane)
Salvinorin A is the active constituent in Salvia divinorum. Apart from THC and the constituents in essential oils, it is the only known nonnitrogenous psychoactive plant constituent. Salvinorin is not an alkaloid.
The substance was first described by Ortega et al., who named it salvinorin (1982). The same substance was subsequently described under the name divinorin A (Valdes et al. 1984). Salvinorin A is extracted from fresh plant material. The effective dosage is between 200 and 500 μ.
Salvinorin A can be smoked in a glass pipe; a better technique involves vaporizing the plant and then inhaling the fumes. It can also be taken in solution under the tongue. When the substance is smoked or inhaled, the effects are immediately apparent, and the primary effects last from five to ten minutes. When it is administered sublingually, the effects become manifest after about ninety seconds and reach their peak some ten to fifteen minutes later, after which they gradually diminish (Turner 1996).
The potent and strange psychoactive effects of salvinorin A were probably discovered by Daniel Siebert:
Salvinorin A is an extremely powerful compound for altering consciousness. In fact, it is the most potent naturally occurring hallucinogen that has been isolated to date. But before potential experimenters become too interested, it must be clearly stated that the effects are often extremely unnerving and that there is a very real risk that persons may physically harm themselves when using it. . . .
I have seen people get up and jump across the room, thereby falling over the furniture, babbling incomprehensible nonsense, and hitting their heads against the wall. Several people tried to leave the house. When the experience was over, they did not remember what had happened. In fact, they actually believed that they remembered entirely different events. To an outside observer, it appears as though these people have an empty expression in their eyes, as though they are not present (and perhaps they really are not). (Siebert 1995, 4)
This description is strongly reminiscent of phenomena that occur with high dosages (overdoses) of nightshades (Atropa belladonna, Brugmansia spp., Hyoscyamus niger, Datura spp.) and the tropane alkaloids atropine and scopolamine. Most subjects have no desire at all to repeat an experiment with salvinorin.
The neurochemistry of salvinorin A is still unresolved. In spite of extensive receptor testing (NovaScreen method), salvinorin A has not been found to bind to any known neurotransmitter receptors, including the receptor that ketamine occupies (David Nichols, pers. comm.). The daring and extreme experiments of D. M. Turner suggest that salvinorin A does not have any negative cross-tolerance with other psychoactive substances (such as LSD, N,N-DMT, ketamine) (Turner 1996).
Commercial Forms and Regulations
“Salvinorin A is the end of everything!”
ANDREW WEIL (1/1995)
Salvinorin, the active constituent of the sage known as ska maría pastora (Salvia divinorum), has the reputation of being the most extreme of all psychedelics. (Book cover, 1996)
See also the entries for Coleus blumei, Salvia divinorum, and diterpenes.
Ortega, A., J. F. Blount, and P. S. Marchand. 1982. Salvinorin, a new trans-neoclerodane diterpene from Salvia divinorum (Labiatae). Journal of the Chemical Society, Perkin Transactions I:2505–8.
Siebert, Daniel J. 1995. Salvinorin A: Vorsicht geboten. Entheogene 3:4–5.
Turner, D. M. 1996. Salvinorin: The psychedelic essence of Salvia divinorum. San Francisco: Panther Press.
Valdes, Leander, William M. Butler, George M. Hatfield, Ara G. Paul, and Masato Koreeda. 1984. Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint Salvia divinorum. Journal of Organic Chemistry 49 (24): 4716–20.
Hyoscin, (–)-hyoscin, hyoscine, hyoszin, L6(–),7-epoxytropin-tropate, l-hyoscine, scopolamin, [7(S)-(1α,2β,4β,5α,7β)]-α-(hydroxymethyl) benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo-[3.3.1.02,4] non-7-ylester, skopolamin, tropane acid ester of skopolin
Empirical formula: C17H21ON4
Substance type: tropane alkaloid
Scopolamine was first isolated in 1888 by E. Schmidt from the roots of “Scopolia atropoides” (= Scopolia carniolica). It is very closely related to atropine and is a characteristic component of plants from the Nightshade Family (Solanaceae), especially the psychoactive species. For the pharmaceutical industry, the most important sources of scopolamine are the Australian duboisias (Duboisia spp.), the dried leaves of which can contain up to 7% alkaloids. Scopolamine is also produced by the recrystallization of hyoscyamine.
For medicinal purposes, scopolamine is administered at dosages of 0.5 to 1 mg, with a total daily maximum dosage of 3 mg. The lowest lethal dosage for humans is about 14 mg (Roth et al. 1994:921*).
Scopolamine is a very potent hallucinogen that
Leuner (1981*) classified as a “Class II” hallucinogen because of its simultaneously hallucinogenic and narcotic/consciousness-clouding effects (cf. also Dittrich 1996*).
According to Hunnius, scopolamine is utilized in medicine as a hypnotic agent, especially for cases of “agitated states in the mentally ill, for Parkinson’s and paralysis agitans, and for treating withdrawal of morphine users” (Hunnius 1975, 609*).
In contrast to atropine, which initially stimulates the central nervous system, scopolamine induces predominantly a narcotic paralysis from the beginning, which is why it serves as a “chemical straitjacket” for agitated mental patients. Delirium and hallucinations are not infrequently seen . . . with therapeutic application. . . . Chronic scopolamine poisoning with gradually increasing dosages leads to psychoses with hallucinations. (Fühner 1943, 202 f.*)
In the former East Germany, scopolamine was still being used as a “chemical straightjacket” in the 1980s (Ludwig 1982, 148*; Schwarz 1984). Scopolamine may be combined with morphine for the same purpose (Römpp 1950, 264*). A combination of scopolamine hydrobromide and morphine hydrochloride is used as a preoperative anesthesia (cf. soporific sponge). Recent tests with mice found that scopolamine hydrobromide causes a marked increase in anxiety as compared to scopolamine methylbromide (Rodgers and Cole 1995).
To treat motion sickness—a use to which scopolamine has long been put (Römpp 1950, 265*)—an adhesive patch was developed that contains 1.5 mg scopolamine and can be adhered behind the ear as needed. The active component is absorbed through the skin into the blood vessels of the ear region and affects the organs of balance in the ear. This property of scopolamine supports the idea that the constituents found in witches’ ointments could be absorbed when the mixtures were rubbed onto the skin.
Scopolamine was a popular inebriant in the Munich jazz scene of the 1950s. Because the dosages used were often so high, many of the concerts had to end early.
Commercial Forms and Regulations
The alkaloid is available as scopolamine hydrobromide and scopolamine hydrochloride. Pharmacies usually carry these substances in the form of small flasks for use in injections. Scopolamine requires a prescription.
Plants Containing Scopolamine
(from Festi 1995*; Hagemann et al. 1992; Ripperger 1995; supplemented)
See also the entries for Atropa belladonna, cocaine, and tropane alkaloids.
Flicker, C., M. Serby, and S. H. Ferris. 1990. Scopolamine effects on memory, language, visuospatial praxis and psychomotor speed. Psychopharmacology 100:243–50.
Hagemann, K., K. Piek, J. Stöckigt, and E. W. Weiler. 1992. Monoclonal antibody-based enzyme immunoessay for the quantitative determination of the tropane alkaloid, scopolamine. Planta Medica 58:68–72.
Heimann, Hans. 1952. Die Skopolaminwirkung. Basel and New York: S. Karger.
Keeler, M. H., and F. J. Kane. 1968. The use of hyoscyamine as a hallucinogen and intoxicant. American Journal of Psychiatry 124:852–54.
Ripperger, Helmut. 1995. (S)-scopolamine and (S)-norscopolamine from Atropanthe sinensis. Planta Medica 61:292–93.
Rodgers, R. J., and J. C. Cole. 1995. Effects of scopolamine and its quaternary analogue in the murine elevated plus-maze test of anxiety. Behavioral Pharmacology 6:283–89.
Schwarz, H.-D. 1984. Hyoscin (= Scolpolamin) statt Zwangsjacke. Zeitschrift für Phytotherapie 5 (3): 840–41.
Chrysatropasäure, gelseminsäure, scopoletina, scopolétine, 7-hydroxy-6-methoxycumarine, 6-methoxyumbelliferon, skopoletin, 3-methylesculetin
Empirical formula: C10H18O4
Substance type: coumarin
The coumarin-derivative scopoletin was first isolated from the genus Scopolia and is named for the genus (Chaubal and Iyer 1977). Scopoletin is found in numerous plants that are utilized for medicinal or psychoactive purposes. It is the characteristic constituent in Brunfelsia spp. (Mors and Ribeiro 1957).
Scopoletin is known to inhibit plant growth. It may possibly have a certain psychoactive effect on humans, although there is no data at present to support this assertion. Scopoletin is a substance that clearly merits additional research.
Commercial Forms and Regulations
See also the entries for Fabiana imbricata and coumarins.
Chaubal, M., and R. P. Iyer. 1977. Carbon-13 NMR spectrum of scopoletin. Lloydia 40:618.
Mors, W. B., and O. Ribeiro. 1957. Occurrence of scopoletin in the genus Brunfelsia. Journal of Organic Chemistry 22:978–79.
Schilcher, H., and R. St. Effenberger. 1986. Scopoletin und β-Sitosterol—zwei geeignete Leitsubstanzen fur Urtica radix. Deutsche Apotheker-Zeitung 126:79–81.
Plants Containing Scopoletin
Estricnina, stricnina, strychnidin-10-on, strychnin, 2,4a,5,5a,8,15a,15b,15c-decahydro-4,6-methano-14H,16H-indolo[3,2,1,ij]oxepino-[2,3,4-de]-pyrrolo[2,3-h]chinolin-14-on
Empirical formula: C21H22N2O2
Substance type: indole alkaloid, strychnos alkaloid
Strychnine was first isolated in 1818 by Caventou and Pelletier from the Philippine Ignatius bean (Strychnos ignatii Berg.; cf. Strychnos spp.). Strychnine occurs in many Strychnos species (Loganiaceae); the primary sources are Strychnos nux-vomica and Strychnos ignatii. Contrary to widespread belief, the hairs of Lophophora williamsii do not contain any strychnine!
Strychnine is an analeptic, a substance that at low dosages activates certain parts of the central nervous system and in higher dosages acts as a convulsive poison:
Milligram dosages of strychnine nitrate administered internally or subcutaneously cause an increased sensitivity of the senses (the feeling that vision, hearing, taste, smell are more acute) and faster reflex response. (Fühner 1943, 221*)
Strychnine docks to the glycine receptor. At lower dosages it is clearly psychoactive, in a manner very similar to yohimbine. The therapeutic dosage for tonic purposes is listed as 1 to 3 mg; a dosage of 5 mg produces aphrodisiac and psychoactive effects. However, 10 mg can cause convulsions, and dosages above 30 mg can lead to difficulty in breathing and severe anxiety (Neuwinger 1994, 527*). From 100 to 300 mg is normally regarded as a lethal dosage for adults, while dosages as low as 1 to 5 mg can prove fatal to small children (Roth et al. 1994, 935*). Strychnine is an extremely stable molecule and could still be detected in corpses that were exhumed as much as four years after burial (Roth et al. 1994, 935*). Diazepam is recommended as an antidote in cases of strychnine poisoning or overdose (Moeschlin 1980). Kavapyrones and kava-kava can also be used as antidotes for strychnine poisoning (cf. Piper methysticum).
Strychnine is also an effective aphrodisiac, but the dosage must be very precise:
The literature contains numerous references to the stimulating effects of strychnine on the sexual apparatus. Many experienced immediate erections. But the extraordinary toxicity of the substance makes it an especially dangerous aphrodisiac. Strychnine has for this reason always played a dangerous role in criminality in this regard as well. (Hirschfeld and Linsert 1930, 210*)
A very effective recipe for a “firm erection” can be prepared with strychnine and other substances (from Gotttlieb 1974, 81*):
5 mg yohimbine hydrochloride
5 mg methyltestosterone
25 mg pemoline
2 mg strychnine sulfate
Strychnine is said to have been the favorite drug of Adolf Hitler, who also appears to have used cocaine (Schmidbauer and vom Scheidt 1984, 260*):
Moreover, we will never know if and how Hitler’s strategy and war leadership might have changed if he had not been making his decisions while in a euphoric trance state induced by high dosages of strychnine. . . . (Irving 1980, 135)
Strychnine has also had an impact on sports because of its prominent role as a doping agent (Schmidbauer and vom Scheidt 1984, 289*).
Strychnine is a popular rat poison and is still used for this purpose today. In the United States, the members of some rather extreme Christian sects drink such rat poisons as an ordeal and an inebriant during their worship services. It is said that the Holy Spirit will protect the true believers from dying from the poison. Surprisingly, these cults have not yet become extinct.
Commercial Forms and Regulations
The substance is available in the form of a base and as strychnine hydrochloride, strychnine nitrate, strychnine phosphate, and strychnine sulfate. All forms of the substance are subject to the regulations concerning dangerous substances. Strychnine is listed in Class 1 of the Swiss Poison List. In principle, however, strychnine is legal.
Poison nuts or crow’s eyes (the seeds of Strychnos nux-vomica) contain high concentrations of strychnine. (Engraving from Pereira, De Beginselen der Materia Medica en der Therapie, 1849)
“The symptoms of strychnine are marked by spontaneous convulsions and states of nervousness in animals.”
HANS HAAS AND HANS FRIEDRICH ZIPF
“ÜBER DIE ERREGENDE WIRKUNG VON BARBITURSÄUREABKÖMMLINGEN UND IHRE BEEINFLUSSUNG DURCH STRYCHNIN, PERVITIN UND CARDIAZOL” [ON THE STIMULATING EFFECT OF BARBITURIC ACID DERIVATIVES AND THE INFLUENCE OFSTRYCHNINE, PERVITIN, AND CARDIAZOL UPON THEM]
See also the entries for Strychnos nux-vomica and Strychnos spp.
Haas, Hans, and Hans Friedrich Zipf. 1949. Über die erregende Wirkung von Barbitursäureabkömmlingen und ihre Beeinflussung durch Strychnin, Pervitin und Cardiazol. Archiv für experimentelle Pathologie und Pharmakologie 206 (5/6): 683–97.
Irving, David. 1980. Wie krank war Hitler wirklich? Munich: Wilhelm Heyne Verlag.
Moeschlin, S. 1980. Klinik und Therapie der Vergiftung. 6th ed. Stuttgart: Thieme.
Seeger, R., and H. G. Neumann. 1986. Strychnin/Brucin. Deutsche Apotheker Zeitung 126 (26): 1386–88.
Δ9-tetrahydrocannabinol, Δ9-THC, delta-9-THC, Δ1-3,4-trans-tetrahydrocannabinol, tetrahydro-6,6,9 -trimethyl-3-pentyl-6H-di-benzo[b,d]pyran-1-ol, trans-THC
Empirical formula: C21H30O2
Substance type: cannabinoid, pyrane derivative, pyranol derivative
THC is the main active constituent of the three hemp species Cannabis indica, Cannabis ruderalis, and Cannabis sativa. THC has not yet been found in any other plants. The information suggesting that THC is pyrochemically synthesized when olibanum (the resin of Boswellia sacra) is burned is contradictory. Similarly, no trace of THC or its analogs has yet been found in hops (Humulus lupulus). THC and its metabolites have been found in Egyptian mummies (Balabanova et al. 1992*).
While trans-THC is psychoactive, the isomer cis-THC is not (Kempfert 1977):
The effective dosage of THC when smoked is between 2 and 22 mg and when taken orally is between 20 and 90 mg. When smoked under normal conditions, 16 to 19% of the THC is consumed and the rest is pyrolized. No lethal dosage is known. However, experiments with animals indicate that the ratio between an effective and a lethal dosage can be estimated to be 4,000 to 40,000. In comparison, this ratio for alcohol is 4 to 10. (Fromberg 1996, 37)
In the blood, THC is transformed into the active metabolite 11-hydroxy-Δ9-THC. This substance is absorbed by fatty tissues after about thirty minutes and is then released back into the blood, metabolized, and excreted. After only a few days, all of the substance has been excreted by the body.With chronic use, 11-hydroxy-THC accumulates in the fatty tissues and in the liver and can be detected for a longer period of time (urine tests!; cf. Rippchen 1996).
THC receptors have been discovered both in the central nervous system and in the peripheral pathways (Compton 1993; Devane et al. 1989; Matsuda et al. 1990). The THC or cannabinoid receptor in the nervous system has now been studied extensively and is very well understood (Pertwee 1995). Normally, endogenous neuro-transmitters known as anandamides bind to these receptors (Devane et al. 1992; Devane and Axelrod 1994; Kruszka and Gross 1994). Nerve diseases (such as multiple sclerosis) can result if the body does not produce sufficient amounts of anandamides. If anandamide deficiencies are responsible for these diseases, it is possible that they could be successfully treated with THC (Mechoulam et al. 1994).
Anandamide (= arachidonylethanolamide)—the name is derived from the Sanskrit word ananda, “bliss”—binds to THC receptors in the brain and is the endogenous THC analog, even though the inner structures of the two are quite different. Recently, anandamide has been discovered in chocolate and cocoa beans (Theobroma cacao) as well as in red wine (cf. Vitis vinifera) (Grotenhermen 1996).
Since 1971, cannabis products have been tested experimentally as medicines for treating alcoholism, heroin and amphetamine addiction, emotional disturbances, muscle spasms, and glaucoma. In 1990, the microbiologist Gerald Lancs of the University of South Florida discovered that marijuana kills the herpes virus (AFP announcement on May 16, 1990), providing scientific validation of an old Roman remedy for herpes. The traditional use of hemp products for asthma has also received scientific support: “THC dilates the bronchial passages. Like other medicines, it can be inhaled as an aerosol to treat bronchial asthma and produces equally positive effects” (Maurer 1989, 48).
The medicinal use of THC and its analogs for the treatment of glaucoma has become an established practice. No other substance has been demonstrated to be better tolerated or more effective than THC (Maurer 1989). A Swiss group of researchers was able to show that THC relaxes the muscular cramping associated with central nervous system spasticity (e.g., due to multiple sclerosis or spinal cord injury) (Maurer et al. 1990). The researchers found that THC (at a dosage of 5 mg) produces effects that are similar to those of codeine but more effective and that THC is also more easily tolerated. There have also been encouraging attempts to utilize THC in the clinical treatment of spasticity and the associated pain (Hagenbach 1996).
“While cannabis and chocolate do not contain the same substances, they do produce similar effects. Moreover, the body itself also produces the substance in chocolate. These substances were named anandamides, after the Sanskrit word for bliss.”
FRANJO GROTENHERMEN “SCHOKOLADE, HASCHISCH UND ANANDAMIDE” [CHOCOLATE, HASHISH, AND ANANDAMIDE] (1996, 14)
THC is the main active constituent in the resin produced by the hemp plant. (Engraving from Pereira, De Beginselen der Materia Medica en der Therapie, 1849)
The potential applications [of synthetic THC] range from the treatment of epilepsy, chronic pain, multiple sclerosis, and lack of appetite to a reduction in the “addictive pressure” associated with opiate addiction. (Schmidt 1996, 30)
Synthetic THC is better known by the trade name Marinol. A dosage of 20 to 45 mg of Marinol induces a “high” that lasts for only sixty to ninety minutes. Many patients in the United States who take Marinol complain that the expensive medicine is ineffective compared to marijuana when either smoked or eaten (Jack Herer, pers. comm.).
Pharmacological research is now under way to develop synthetic THC analogs that could be marketed as medicines. The goal is to isolate the medically useful properties of THC while removing the psychoactive ones (Evans 1991). One of the products that has been synthesized as a result of this research is the cannabinoid analog HU-210, chemically known as (–)1l-OH-Δ8-THC-dimethylheptyl. This substance not only is psychoactive but is some one hundred to eight hundred times more potent than natural THC (Ovadia et al. 1995). However, government health departments and pharmaceutical companies are more interested in THC analogs that are devoid of psychoactive effects. Some critics of this research take a different position, arguing that the therapeutic effects of THC are directly related to its psychoactivity.
Commercial Forms and Regulations
In principle, THC is an illegal substance throughout the world (cf. Cannabis indica). However, for the past several years certain prescription drugs containing THC have been available in the United States under the trade names Canasol and Marinol. Physicians may prescribe these for glaucoma and cancer patients. In Europe, these drugs can be obtained only from pharmacies that sell foreign medicines, and they are extremely expensive. Recently, there have been efforts in several states in the United States as well as in several European nations to make THC and/or Cannabis products more readily available to patients suffering from a variety of conditions. There is, however, considerable resistance to such liberalization efforts. In spite of the very long history of use of THC and Cannabis in numerous cultures and for a wide variety of purposes (see Rätsch 2001*), it remains to be seen whether these substances will ever become widely accepted and legitimately used.
“While a person who smokes cannabis can at most smoke [himself or herself] to sleep and an overdose is not possible, a handful of THC capsules is sufficient to induce unconsciousness in a person for a long time. In addition to this flaw, the occasional indications of psychosis as well as such side effects as sleep disorders that last for weeks, irritability, and diarrhea speak against the use of the synthetic substance. It appears as though the gentle drug has been turned into a bitter pill in the laboratory.”
“DIE THC-PILLE AUF REZEPT” [THE THC PILL ON PRESCRIPTION] (1996, 31)
The cocoa tree produces anandamide (or a precursor) in its fruits. Anandamide is the substance that binds to the THC or cannabinoid receptors in the human brain. (Engraving from Peireira, De Beginselen der Materia Medica en der Therapie, 1849)
See also the entries for Cannabis indica and Cannabis sativa.
Compton, David R., Kenner C. Rice, Brian R. de Costa, Raj K. Razdan, Lawrence S. Melvin, M. Ross Johnson, and Billy R. Martin. 1993. Cannabinoid structure-activity relationships: Correlation of receptor binding and in vivo activities. The Journal of Pharmacology and Experimental Therapeutics265:218–26.
Devane, William A., and Julius Axelrod. 1994. Enzymatic synthesis of anandamide, an endogenous ligand for the cannabinoid receptor, by brain membranes. Proceedings of the National Academy of Science, USA 91:6698–701.
Devane, William A., Francis A. Dysarz III, M. Ross Johnson, Lawrence S. Melvin, and Alynn C. Howlett. 1988. Determination and characterization of a cannabinoid receptor in rat brain. Molecular Pharmacology 34:605–13.
Devane, William A., Lumir Hanus, Aviva Breuer, Roger G. Pertwee, Lesley A. Stevenson, Graeme Griffin, Dan Gibson, Asher Mandelbaum, Alexander Etinger, and Raphael Mechoulam. 1992. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258:1946–49.
Evans, Fred J. 1991. Cannabinoids: The separation of central from peripheral effects on a structural basis. Planta Medica 57 suppl. (1): 60–67.
Fromberg, Erik. 1996. Die Pharmakologie von Cannabis. In Cannabis, ed. Jürgen Neumeyer, 36–42. [Munich]: Packeispresse Verlag Hans Schickert.
Grotenhermen, Franjo. 1996. Schokolade, Haschisch und Anandamide. Hanf! 12/96:14–15.
Hagenbach, Ulrike. 1996. Spinale Spastik und Spasmolyse: Ist die Therapie mit THC eine unerwartete Bereicherung? In Jahrbuch des Europäischen Collegiums für Bewußtseinsstudien (1995), 199–207. Berlin: VWB.
Iversen, Leslie L. 1993. Medical uses of marijuana? Nature 365:12–13.
Kettenes-van den Bosch, J. J., and C. A. Salemink. 1980. Biological activity of the tetrahydrocannabinols. Journal of Ethnopharmacology 2:197–231. (Very good bibliography.)
Kruszka, Kelly K., and Richard W. Gross. 1994. The ATP- and coA-independent synthesis of arachidonoylethanolamide: A novel mechanism underlying the synthesis of the endogenous ligand of the cannabinoid receptor. The Journal of Biological Chemistry 269 (20): 14345–48.
Matsuda, Lisa A., Stephen J. Lolait, Michael J. Brownstein, Alice C. Young, and Tom I. Bonner. 1991. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346:561–64.
Maurer, Maja. 1989. Therapeutische Aspekte von Cannabis in der westlichen Medizin. In 3. Symposion über psychoaktive Substanzen und veränderte Bewußtseinszustände in Forschung und Therapie, ed. M. Schlichting and H. Leuner, 46–49. Göttingen: ECBS.
Maurer, M., V. Henn, A. Dittrich, and A. Hofmann. 1990. Delta-9-tetrahydrocannabinol shows antispastic and analgesic effects in a single case double-blind trial. European Archives of Psychiatry and Clinical Neuroscience 240:1–4.
Mechoulam, Raphael, Zvi Vogel, and Jacob Barg. 1994. CNS cannabinoid receptors: Role and therapeutic implications for CNS disorders. CNS Drugs 2 (4): 255–60.
Mestel, Rosie. 1993. Cannabis: The brain’s other supplier. New Scientist 7/93:21–23.
Ovadia, H., A. Wohlman, R. Mechoulam, and J. Weidenfeld. 1995. Characterization of the hypothermic effect of the synthetic cannabinoid HU-210 in the rat: Relation to the adrenergic system and endogenous pyrogens. Neuropharmacology 34 (2): 175–80.
Pertwee, Roger, ed. 1995. Cannabinoid receptors. New York: Harcourt Brace Jovanovich.
Rippchen, Ronald, ed. . Mein Urin gehört mir. Lörbach: Edition Rauschkunde.
Schmidt, Sebastian. 1996. Die THC-Pille auf Rezept. Hanfblatt 3 (20): 30–31.
Smith, R. Martin, and Kenneth D. Kempfert. 1977. Δ1-3,4-cis-tetrahydrocannabinol in Cannabis sativa. Phytochemistry 16:1088–89.
Zeeuw, Rokus A. de, and Jaap Wijsbeek. 1972. Cannabinoids with a propyl side chain in cannabis: Occurrence and chromatographic behavior. Science 175:778–79
Tropanalkaloide, tropanes, tropeine
Tropane alkaloids are esters of tropanal combined with various acids. They occur primarily in nightshades (Solanaceae), especially the psycho-active ones. The most important psychoactive tropane alkaloids are atropine, scopolamine, and hyoscyamine. These substances are “quickly absorbed through the mucous membranes but also through the intact skin” (Roth et al. 1994, 944*). For this reason, plant preparations in the form of ointments with these tropane alkaloids can induce psychoactive effects (cf. Datura innoxia, witches’ ointments). Atropine, scopola-mine, and hyoscyamine are found in the genera Atropa, Brugmansia, Datura, Hyoscyamus, Iochroma, Juanulloa, Mandragora, Solandra, and Scopolia.
The psychoactive tropane alkaloid hyoscyamine (cf. Hyoscyamus niger) occurs in the following nightshades in concentrations that appear to make them useful for psychoactive purposes (Festi 1995, 132 f.*): Anthoceris littoreaLabill. (herbage), Crenedium spinescens Haegi (leaves), Cyphanthera anthocercidea (F.v. Muell.) Haegi (leaves), Mandragora caulescens C.B. Clarke (entire plant; cf. Mandragoraspp.), Physochlaina praealta (Decne.) Miers (entire plant), and Scopolia lurida Dunal (roots; cf. Scopolia carniolica). As a plant dries, the hyoscyamine it contains is usually transformed into its analog scopolamine. The profile of effects of hyoscyamine is essentially the same as that of scopolamine.
Tropanes and cocaine are chemically related and can under certain conditions elicit similar pharmacological effects (Sauerwein et al. 1993). The tropane alkaloid 2-tropanone is a metabolic product of cocaine. Tropane alkaloids occur in most if not all Erythroxylum species (Al-Said et al. 1989). The bark of Erythroxylum zambesiacum N. Robson has been found to contain various tropanes (Christen et al. 1993). The root bark of Erythroxylum hypericifoliumLam., a species indigenous to Mauritius that is used in folk medicine to treat kidney problems, contains large amounts of hygrine as well as other tropanes (e.g., cuscohygrine) (Al-Said et al. 1989). Both hygrine and cuscohygrine are also found in the leaves and bark of the two coca species Erythroxylum coca and Erythroxylum novogranatense (Al-Said et al. 1989, 672). The leaves of the Southeast Asian species Erythroxylum cuneatum (Wall.) Kurz, which is used in Malaysia as a tonic, were found to contain as their primary alkaloid (±)-3α,6β-dibenzoyloxytropane; another major constituent in the leaves is nicotine. The main alkaloid in the leaves of another ethnomedicinally useful Southeast Asian species, Erythroxylum ecarinatum Burck., is tropacacaine. The root bark of the Australian species Erythroxylum australe F.v. Muell. also contain numerous tropanes (meteloidine) (El-Imam et al. 1988).
The tropane alkaloids are typical constituents of almost all members of the Nightshade Family (Solanaceae). (A Lycianthes species from South America)
“But how does it happen that people ill with fevers or who are destroying their nervous system with narcotics—in other words, making it more sensitive—‘imagine’ that they see gruesome faces when their consciousness is dulled? Why do mice, after having been injected with hyoscyamine, raise themselves up on their hind legs—something they would normally never do when they see an enemy—and with gestures of utmost terror betray to us that they are perceiving something that is hidden from our senses?”
GUSTAV MEYRINK SÜDSEE-MASKEN/DAS HAUS DER LETZTEN LATERN 1 [SOUTH SEA MASKS/THE HOUSE OF THE LAST LANTERN 1] (REISSUE 1973)
Tropane alkaloids also appear to be present in the Proteaceae Family, e.g., in the species Knightia strobolina (El-Imam et al. 1988:2182). In Australia, several members of the genera Hakea and Banksia are used to produce wine.
The recent discovery of tropane alkaloids (tropine, tropinone, cuscohygrine, hygrine) in field bindweed (Convolvulus arvensis L.; cf. Convolvulus tricolor) is very interesting; the species also contains ergot alkaloids (Todd et al. 1995). Tropane alkaloids have also been found in the hedge bindweed Calystegia sepium (L.) R. Br. [syn. Convolvulus sepium] (Goldmann et al. 1990).
See also the entries for atropine and scopolamine.
Bauer, Eduard. 1919. Studium über die Bedeutung der Alkaloide in pharmakognostisch wichtigen Solanaceen, besonders in Atropa Belladonna und Datura Stramonium. Bern: Hallwag.
Christen, P., M. F. Roberts, J. D. Phillipson, and W. C. Evans. 1993. Recent aspects of tropane alkaloid biosynthesis in Erythroxylum zambesiacum stem bark. Planta Medica 59 suppl.: A583–84.
Goldmann, Arlette, Marie-Louise Milat, Paul-Henri Ducrot, Jean-Yves Lallemand, Monique Maille, Andree Lepingle, Isabelle Charpin, and David Tepfer. 1990. Tropane derivates from Calistegia sepium. Phytochemistry 29 (7): 2125–27.
Imam, Yahia M. A. el-, William C. Evans, and Raymond J. Grout. 1988. Alkaloids of Erythroxylum cuneatum, E. ecarinatum and E. australe. Phytochemistry 27 (7): 2181–84.
Said, Mansour S. al-, William C. Evans, and Raymond J. Grout. 1989. Alkaloids of Erythroxylum hypericifolium stem bark. Phytochemistry 28 (2): 671–73.
Sauerwein, M., F. Sporer, and M. Wink. 1993. Allelochemical properties of derivatives from tropane and ecgonine. Planta Medica 59 suppl.: A662
Todd, G. Fred, F. R. Stermitz, P. Schultheiss, A. P. Traub-Dargatz, and J. Traub-Dargatz. 1995. Tropane alkaloids and toxicity of Convolvulus arvensis. Phytochemistry 39:301–3.
Xiao, P., and L. Y. He. 1983. Ethnopharmacologic investigation on tropane-containing drugs in Chinese Solanaceous plants. Journal of Ethnopharmacology 8:1–18.
Withanolides are not alkaloids but C28 steroidal lactones. More than one hundred withanolides have been isolated and described to date (Christen 1989). They occur only (or primarily) in members of the Nightshade Family (Solanaceae) (Christen 1989; Evans et al. 1984; Lavie 1986).
The withanolides withaferine A and withanolide E have very interesting biological and pharmacological effects: they are antinflammatory, stimulate the immune system, and inhibit the formation of tumors (Christen 1989). Despite the fact that many plants with psychoactive properties contain only or primarily withanolides, not a single psychoactive constituent from this group has been isolated or described to date.
The shoo-fly or apple-of-Peru (Nicandra physalodes; Solananceae), a plant from Peru, contains primarily withanolides and produces an effect similar to that of hyoscyamine. This may be the reason behind the French name for the plant: belladonne de pays, “belladonna of the countryside.”
The central European hedge bindweed (Calystegia sepium) contains psychoactive tropane alkaloids. (Photographed in Schönbrühl, near Bern, Switzerland)
See also the entries for Withania somnifera.
Buddhiraja, R. D., and S. Sudhir. 1987. Review of biological activity of withanolides. Journal of Scientific and Industrial Research 46:488–91.
Christen, P. 1989. Withanolide: Naturstoffe mit vielversprechendem Wirkungsspektrum. Pharmazie in unserer Zeit 18 (5): 129–39.
Evans, William C., Raymond J. Grout, and Merlin L. K. Mensah. 1984. Withanolides of Datura spp. and hybrids. Phytochemistry 23 (8): 1717–20.
Lavie, David. 1986. The withanolides as a model in plant genetics: Chemistry, biosynthesis, and distribution. In Solanaceae: Biology and systematics, ed. William G. D’Arcy, 187–200. New York: Columbia University Press
Plants Containing Withanolides
Aphrodin, corymbin, corynin, hydroergotocin, johimbin, quebrachin, quebrachina, yohimbenin, yohimbin, yohimbina, yohimbinum, yohimvetol
Empirical formula: C21H26N2O3
Substance type: aspidosperma alkaloid, indole alkaloid
Yohimbine was first extracted from the bark of Pausinystalia yohimba and described in the nineteenth century. It is a typical alkaloid in plants from the Apocynaceae Family and is related to the Rauvolfia alkaloids, and it constitutes the primary alkaloid (1%) in Alstonia angustifolia. It is also present in some species of Rauvolfia, especially the African species Rauvolfia macrophylla Stapf (Timmins and Court 1974).
Yohimbine was once regarded as an MAO inhibitor, a view that is no longer considered accurate. Rather, it is simply an α-adrenergic blocker that consequently stimulates the release of nor-adrenaline at the nerve endings. This makes noradrenaline available in the corpus cavernosum and results in an erection (Roth et al. 1994, 955*; Wren 1988, 292*).
As a sympathicolytic agent, [yohimbine] dilates the peripheral blood vessels and reduces blood pressure. The aphrodisiac effect is explained through a vasodilatation of the genital organs and an increased excitability of the reflexes in the sacral medulla. (Roth et al. 1994, 545*)
Yohimbine’s aphrodisiac and virility-enhancing effects, and its therapeutic efficaciousness in treating impotence, have been demonstrated in a number of clinical double-blind studies (Buffum 1982; Miller 1968; Sobotka 1969).507Consequently, yohimbine hydrochloride has been approved as a specific medicine for the treatment of impotence (sexual neurasthenia). The recommended dosage is 5 to 10 mg taken three times daily as a short-term treatment over three to four weeks. Higher individual dosages (15 to 25 mg) result in psychoactive effects that are somewhat reminiscent of those of LSD, but with much less emotional content and an emphasis on physical phenomena (sexual desire, erotic enjoyment, and increased sensations of pleasure). Overdoses can be unpleasant but do not appear to be particularly dangerous (cf. Lewin 1992, 750*):
A chemist had taken an almost 1000-fold dosage (1.8 g). He became unconscious for a few hours (during which time a pronounced priapism was observed) but was able to be discharged from the hospital within a day. (Roth et al. 1994, 956*)
Plants Containing Yohimbine
(from Geschwinde 1996, 145 f.*; Hofmann 1954; Lewin 1992*; Römpp 1995, 5093*; Roth et al. 1994*; supplemented)
Yohimbine is a characteristic constituent in the bark of many Alstonia species, some of which have been traditionally utilized as aphrodisiacs. (Alstonia macrophylla, photographed in Hawaii)
Commercial Forms and Regulations
The alkaloid is available as yohimbine hydro-chloride. Yohimbine is a prescription medication.
“Yohimbe acts both as a central nervous-system stimulant and as a mild hallucinogen. . . . The first effects are a lethargic weakness of the limbs and a vague restlessness, similar to the initial effects of LSD. Chills and warm spinal shivers may also be felt, along with slight dizziness and nausea. . . . Then the effects produce a relaxed, somewhat inebriated mental and physical feeling accompanied by slight auditory/visual hallucinations. Spinal ganglia are then affected, causing erection of the sex organs. These effects last from two to four hours.”
RICHARD ALAN MILLER
THE MAGICAL AND RITUAL USE OF APHRODISIACS
See also the entries for Alstonia scholaris, Corynanthe spp., and Pausinystalia yohimba.
Buffum, John. 1982. Pharmacosexology: The effects of drugs on sexual function—a review. Journal of Psychoactive Drugs 14 (1–2): 5–44.
Finch, N., and W. I. Taylor. 1962. Oxidative transformation of indole alkaloids. 1: Preparation of oxindoles from yohimbine. Journal of the American Chemical Society 84:3871–77.
Hofmann, Albert. 1954. Die Isolierung weiterer Alkaloide aus Rauwolfia serpentina Benth. Helvetica Chimica Acta 37:849–65.
Lambert, G. A., W. J. Lang, E. Friedman, E. Meller, and S. Gershon. 1978. Pharmacological and biological properties of isomeric yohimbine alkaloids. European Journal of Pharmacology 49:39–48.
Leary, Timothy. 1985. Auf der Suche nach dem wahren Aphrodisiakum und elektronischer Sex. Sphinx Magazin 35.
Miller, W. W. 1968. Afrodex in the treatment of male impotence: A double-blind cross-over study. Current Therapeutic Research 10:354–59.
Poisson, J. 1964. Recherches récentes sur les alcaloïdes du pseudocinchona et du yohimbine. Ann. Chim. 9:99–121.
Porst, H. 1996. Orale und intracavernöse Pharmakotherapie. TW Urologie Nephrologie 8 (2): 88–94.
Sobotka, J. J. 1969. An evaluation of Afrodex in the management of male impotency: A double-blind cross-over study. Current Therapeutic Research 11:87–94.
Timmins, Peter, and William E. Court. 1974. Alkaloids of Rauwolfia macrophylla. Phytochemistry 13:281–82.
Weyers, Wolfgang. 1982. Die Empfehlung in der Selbstmedikation. Heusenstamm: Keppler Verlag.