From: pwal1@eng3.eng.monash.edu.au (Paul Walsh) Newsgroups: alt.drugs,alt.drugs.chemistry,bionet.plants,bionet.mycology Subject: Tryptamine FAQ (Last update - August 1994) Date: Tue, 30 Aug 1994 07:48:44 GMT Message-ID: TRYPTAMINE CARRIERS Last update August 1994 =================== by Petrus Pennanen (ppennane@cc.helsinki.fi) with help from Michael from Melbourne (Hex@f362.n632.23.fido.zeta.org.au). Thanks to many individuals for help in putting this together! If you know sources of tryptamines that are not mentioned here please mail us. ORALLY AND PARENTERALLY ACTIVE PSYCHOTROPIC TRYPTAMINE DERIVATIVES Based on McKenna & Towers 1984 R4 R1 | / R5 // \ /\ N \// \ ____/ \ / \ | || || | R2 | || || | \\ /\ / R3 \\ / \ / N H Dosage Route Name of Compound R1 R2 R3 R4 R5 (mg) Oral/Par. ----------------------------------------------------------------------------- tryptamine H H H H H 100 *1 par/oral? DMT (dimethyltryptamine) CH3 CH3 H H H 60 par DET C2H5 C2H5 H H H 60 par/oral DPT n-prop n-prop H H H 60 par/oral DAT C3H5 C3H5 H H H 30 par/oral DIPT i-prop i-prop H H H 30 oral 5-MeO-DIPT i-prop i-prop H H OCH3 12 oral 5-MeO-DMT CH3 CH3 H H OCH3 6 par psilocin CH3 CH3 H OH H 12 *2 oral CZ-74 C2H5 C2H5 H OH H 15 *2 oral serotonin H H H H OH 100 *3 oral bufotenine CH3 CH3 H H OH 16 *4 par IT-290 H H CH3 H H 30 oral 4-hydroxy-alfa-methyl- tryptamine H H CH3 OH H 20 *3 oral MP-809 H H CH3 H CH3 60 *5 oral 5-fluoro-alfa-methyl- tryptamine H H CH3 H F 25 *6 oral 5-methoxy-alfa-methyl- tryptamine H H CH3 H OCH3 3 oral 4-hydroxy-diisopropyl- tryptamine i-prop i-prop H OH H 12 *6 oral 4-hydroxy-N-isopropyl, N-methyl-tryptamine i-prop CH3 H OH H 6 *6 oral N-t-butyl-tryptamine H t-butylH H H ? *7 par? 3-(2-(2,5-dimethyl pyrrolyl)ethyl)-indole H H H ? ? 5-alfa-DMT CH3 CH3 CH3 H H ? ? ----------------------------------------------------------------------------- Data compiled from Kantor, et al. 1980; Shulgin 1976,1982; Shulgin&Carter 1980 *1 Autonomic symptoms; little central activity. *2 The phosphate esters are psilocybin and CEY-19, respectively; both are stoichiometrically equivalent to the 4-hydroxy isomers. *3 Cardiovascular and autonomic symptoms; little central activity. *4 A pressor amine rather than a hallucinogen in man. *5 An antidepressant rather than a hallucinogen in man. *6 Based on anonymous reports in the lay press. No clinical studies have been published. *7 No oral activity with doses up to 20 mg, may be parenterally active. Other potentially psychedelic tryptamines include 6-fluoro-alfa-methyltryptamine, 7-methyltryptamine, 5-methyltryptamine, 5-fluorotryptamine, 6-fluorotryptamine and 5- and 6-fluorotryptophans. MAO Inhibitors and Tryptamines Monoamine oxidase (MAO) is the primary inactivation pathway of most tryptamines. Because of this, inhibitors of the MAO enzyme (MAOIs) can be used to potentiate the effects of tryptamines and to make DMT and 5-MeO-DMT orally active. MAO inhibitors fall into two classes: Irreversible and reversible MAOIs. Irreversible MAOIs (e.g. the hydrazides iproniazid and phenelzine) bind permanently to the enzyme and cause MAO inhibition lasting 1-2 weeks after ingestion. They are used clinically to treat depression. Reversible MAOIs, such as moclobemide, which is used as an antidepressant, and the beta- carbolines harmine and harmaline, are effective for much shorter time, maybe up to 24 hours. Recreational drug users around the world are using mainly harmine and harmaline despite the lack of scientific studies on their effects on humans. Natives of Amazon have traditionally combined Banisteriopsis caapi vine, which contains harmine, harmaline and related beta-carbolines, with DMT- containing plants to make an orally active brew called ayahuasca. Other plants containing harmine and/or harmaline can be substituted for B. caapi. The usual 'North-American ayahuasca' consists of Peganum harmala seeds and Desmanthus illinoensis roots, and in Australian 'acaciahuasca' leaves of Acacia complanata are combined with material from DMT-containing acacias (the effectivity of this mixture hasn't been confirmed). MAOIs have also been used to potentiate the effects of mushrooms containing psilocybin. Terence McKenna has mentioned chocolate being a weak MAOI, which could be a reason for the popular habit of ingesting mushrooms with cocoa. Peganum harmala (Syrian rue) seeds are the most concentrated natural source of harmine and harmaline - about 3% of their weight consists of these alkaloids. Banisteriopsis caapi has been found to contain from 0.18% to 1.36% beta-carbolines, with the concentration of harmine being from 0.057% to 0.635% (McKenna et al. 1984). According to anecdotal reports one gram of P. harmala seeds ingested inhibits MAO enough to make DMT orally active. Harmine and harmaline are hallucinogenic on their own with doses starting from around 300 mg (Naranjo 1967). They have little emotional or 'psychedelic' effects, but produce strong visual hallucinations. Because of this the natives of Amazon often add larger amounts (75-100 cm of stem per dose) of B. caapi to ayahuasca brew than is needed for MAO inhibition (Luna 1984). There are significant dangers in using MAO inhibitors. MAOIs potentiate the cardiovascular effects of tyramine and other monoamines found in foods. Ingestion of aged cheese, beer, wine, pickled herring, chicken liver, yeast, large amounts of coffee, citrus fruits, canned figs, broad beans, chocolate or cream while MAO is inhibited can cause a hypertensive crisis including a dangerous rise in blood pressure. Effects of amphetamines, general anaesthetics, sedatives, anti-histamines, alcohol, potent analgesics and anticholinergic and antidepressant agents are prolonged and intensified. Overdosage of MAOIs by themselves is also possible with effects including hyperreflexia and convulsions. Self-Synthesis of DMT Derivatives Tryptamine derivatives and beta-Carbolines have been detected as endogenous metabolites in mammals, including humans. Methyl transferases that catalyze the synthesis of tryptamines, including DMT, 5-MeO-DMT and bufotenine, are found in human lung, brain, cerebrospinal fluid, liver and heart (McKenna & Towers 1984). In the pineal gland MAO is the primary inactivation pathway of serotonin, a neurotransmitter synthesized from the amino acid tryptophan. If MAO is blocked by harmine, harmaline or other MAO inhibitors serotonin can be converted by the methyltransferase enzymes HIOMT and INMT into psychedelic tryptamines (serotonin --(HIOMT)--> 5-MeO-trypt. --(2*INMT)--> 5-MeO-DMT). So, ingesting l-tryptophan to increase serotonin levels, a candy bar to increase the amount of tryptophan getting to your brain and natural plant material containing 25-50 mg harmine/harmaline to block MAO, all at the same time, is supposed to cause your pineal gland to synthesize substantial amounts of 5-MeO-DMT (Most 1986). This is extremely dangerous for persons with existing amine imbalance or schizophrenia. For normal, healthy people possible consequences are bad. A potent inhibitor of INMT, which is a necessary enzyme for the synthesis of DMT and 5-MeO-DMT, is found in particularly high concentrations in the pineal gland. A bypassing or inhibition of the synthesis of this inhibitor might be responsible for trances and other psychedelic states achieved "without drugs" (Strassman 1990). See Strassman's article for more info and speculation about the pineal gland. Psychedelic Toads Bufotenine and related 5-hydroxy-indolethylamines are common constituents of venoms of the genera Hyla, Leptodactylus, Rana and Bufo. Bufotenine is not psychedelic in reasonable doses (with larger doses there are dangerous physiological side effects), but the skin of one species, Bufo alvarius, contains 50-160 mg 5-MeO-DMT/g of skin (Daly & Witkop 1971). It's the only Bufo species known to contain a hallucinogenic tryptamine (McKenna & Towers 1984). Most (1984) gives instructions for collecting and drying the venom: Fresh venom can easily be collected without harm to the toad. Use a flat glass plate or any other smooth, nonporous surface at least 12-inches square. Hold the toad in front of the plate, which is fixed in a vertical position. In this manner, the venom can be collected on the glass plate, free of dirt and liquid released when the toad is handled. When you are ready to begin, hold the toad firmly with one hand and, with the thumb and forefinger of your other hand, squeeze near the base of the gland until the venom squirts out of the pores and onto the glass plate. Use this method to systematically collect the venom from each of the toad's granular glands: those on the forearm, those on the tibia and femur of the hind leg, and, of course, the parotoids on the neck. Each gland can be squeezed a second time for an additional yield of venom if you allow the toad a one-hour rest preiod. After this the glands are empty and require four to to six weeks for regeneration. The venom is viscous and milky-white in color when first squeezed from the glands. It begins to dry within minutes and acquires the color and texture of rubber cement. Scrape the venom from the glass plate, dry it thoroughly, and store it in an airtight container until you are ready to smoke it. Davis and Weil (1992) smoked the venom and described what happened: In comparison to the pure compounds the toad venom appears longer lasting and, because one does not completely lose contact with reality, far more pleasant, even sensual. Shortly after inhalation I experienced warm flushing sensations, a sense of wonder and well-being, strong auditory hallucinations, which included an insect-cicada sound that ran across my mind and seemed to link my body to the earth. Though I was indoors, there was a sense of the feel of the earth, the dry desert soil passing through my fingers, the stars at midday, the scent of cactus and sage, the feel of dry leaves through hands. Strong visual hallucinations in orblike brilliance, diamond patterns that undulated across my visual field. The experience was in every sense pleasant, with no disturbing physical symptoms, no nausea, perhaps a slight sense of increased heart rate. Warm waves coursed up and down my body. The effects lasted only a few minutes but a pleasant afterglow continued for almost an hour. (Wade Davis, personal observation, January 12, 1991) Profound alteration of consciousness within a few seconds of exhaling. I relax into a deep, peaceful interior awareness. There is nothing scary about the effects and no sense of toxicity. I try to describe my feelings but am unable to talk for the first five minutes and then only with some difficulty. This is a powerful psychoactive drug, one that I think would appear to most people who like the effects of hallucinogens. For the next hour I feel slow and velvety, with a slight pressure in my head. No long-lasting effects to report. (Andrew T. Weil, personal observation, January 12, 1991) The Fungi Family: Bolbitiaceae Genus: Agrocybe Species: farinacea Contains psilocybin (Koike et al. 1981). Genus: Conocybe Species: cyanopus kuehneriana siligineoides smithii C. cyanopus (Benedict et al. 1962) and in C. smithii (Benedict et al. 1967) contain psilocybin and psilocin while C. kuehneriana contains psilocin only (Ohenoja et al. 1987). C. siligineoides may also contain these alkaloids (Schultes & Hofmann 1979 p. 40). Family: Coprinaceae Genus: Copelandia Species: anomala bispora cambodginiensis cyanescens tropicalis All species contain psilocin and psilocybin, for C. cyanescens (Schultes & Hofmann 1979 p. 40) and for C. cambodginiensis as well as C. tropicalis (Arora, 1986), and for C. anomala as well as C. bispora (Merlin & Allen, 1993). Genus: Panaeolina Species: foenisecii P. foenisecii contains psilocybin (Robbers et al. 1962). Genus: Panaeolus Species: antillarum ater campanulatus firmicola olivacens papilionaceus retirugis separatus sphinctrinus subbalteatus Several Panaeolus species contain psilocybin. For P. antillarum refer to Allen et al. (1991), for P. ater refer to Bresinsky et al. (1990), for P. papilionaceus (Gurevich et al. 1992), for P. retirugis (Fiussello et al. 1971/72), for P. separatus (Miller Jr. 1972), for P. sphinctrinus (Hein & Wasson, 1958 p. 322) and for P. olivacens (Ohenoja et al. 1987). P. subbalteatus contains both psilocin and psilocybin (Ohenoja et al. 1987) but was known to be hallucinogenic since 1959 (Stein, 1959). P. firmicola is also described as hallucinogenic and probably contains the same alkaloids (Schultes, 1979). Genus: Psathyrella Species: candollenana Contains psilocybin (Koike et al. 1981) and psilocin (Ohenoja et al. 1987). Family: Cortinariaceae Genus: Galerina Species: steglichii Contains psilocybin and psilocin (Besl, 1993). Genus: Gymnopilus Species: aeruginosus liquiritiae luteus purpuratus spectabilis validipes viridans Many Gymnopilus contain psilocybin, for G. aeruginosus, G. luteus, G. spectabilis, G. validipes and G.viridans refer to Hatfield et al. (1978). For G. liquiritiae (Koike, 1981) and for G. purpuratus (Gartz 1991). Genus: Inocybe Species: aeruginascens coelestium corydalna haemacta tricolor These contain psilocin and psilocybin, for P. aeruginascens refer to Haeselbarth et al. (1985) and for the others Stijve et al. (1985). Family: Pluteaceae Genus: Pluteus Species: atricapillus nigroviridis salicinus P. atricapillus contains psilocybin (Ohenoja et al. 1987) while both P. salicinus (Saupe 1981) and P. nigroviridis (Christiansen et al. 1984) contain psilocin and psilocybin. Family: Strophariaceae Genus: Psilocybe Species: 75 Known Hallucinogenic species + aucklandii coprophila crobulus samuiensis There are at least 75 mushroom species in this genera that contain psilocin and psilocybin in Guzman 1983, and there are several more recently discovered species such as P. aucklandii (Guzman et al. 1993) and P. samuiensis (Guzman et al. 1991). Also P. coprophila, while lacking psilocin (making it a non-blueing psilocybe) is known to contain psilocybin (Arora, 1986). P. crobulus is also known to be hallucinogenic (Phillips, 1981). The Plants Family: Acanthaceae Genus: Justicia Species: pectoralis (var. stenophylla) Waikas of Orinoco headwaters in Venezuela add dried and pulverized leaves of this herb to their Virola-snuff. Intensely aromatic smelling leaves probably contain tryptamines (Schultes 1977). Plants are available from ..Of the jungle (PO Box 1801 sebastopol CA 95473) for $35. Family: Aizoaceae Genus: Delosperma Contains DMT and N-methyltryptamine (see Smith 1977 for references). Family: Alariaceae Genus: Ecklonia Species: maxima DMT is found in brown seaweed extract sold as Kelpak (Crouch et al. 1992). Family: Apocynaceae Genus: Prestonia Species: amazonica? Contains DMT (Smith 1977). Family: Cactaceae Genus: Echinocereus Species: salm-dyckianus triglochidiatus These cacti growing in Mexico are known to Tarahumare Indians as peyote or hikuli and used in their festivals. E. triglochidiatus contains a tryptamine derivative, possibly 5-MeO-DMT (Bye 1979). E. salm-dyckianus is also supposed to contain tryptamines according to Horus Botanicals catalog 1992. Genus: Trichocereus Species: terscheckii "Cardon grande" DMT has been isolated from this species growing in North-Western Argentina (Schultes & Hofmann 1979 p. 58). Family: Caesalpininaceae Genus: Petalostylis species: cassiodies Leaves and stem contain 0.4-0.5% tryptamine, DMT and other alkaloids (Johns et al. 1966). Family: Fabaceae Genus: Desmodium Species: gangetium gyrans tiliaefolium triflorum Leaves, root, stem and seeds contain DMT and 0.06% 5-MeO-DMT of wet weight (Banerjee & Ghosal 1969). Genus: Lespedeza Species: bicolor Leaves and root contain DMT and 5-MeO-DMT (Smith 1977). Seeds of this hardy perennial shrub are available from ..Of the jungle for $5. Genus: Mucuna Species: pruriens Leaves, stem and fruit of this jungle vine contains DMT and 5-MeO-DMT (Smith 1977). Seeds are available from ..Of the jungle for $5. Genus: Phyllodium Species: pulchellum Dried plant material produced 0.2% 5-MeO-DMT and small amounts of DMT (Ghosal & Mukherjee 1966). Family: Mimosaceae Genus: Anadenanthera species: colubrina peregrina Black beans from these trees are toasted, pulverized and mixed with ashes or calcined shells to make psychedelic snuff called yopo by Indians in Orinoco basin in Colombia, Venezuela and possibly in southern part of Brasilian Amazon. Yopo is blown into the nostrils through bamboo tubes or snuffed by birdbone tubes. The trees grow in open plain areas, and leaves, bark and seeds contain DMT, 5-MeO-DMT and related compounds (Schultes 1976,1977; Pachter et al. 1959). Genus: Acacia Species: confusa jurema maidenii niopo nubica phlebophylla polycantha subsp. campylacantha senegal simplicifolia Dried A. confusa stems contain 0.04% N-methyltryptamine and 0.02% DMT (Arthur et al. 1967). The dried leaves of A. phlebophylla contain 0.3% DMT (Rovelli & Vaughan 1967). The bark of A. maidenii contains 0.6% of N-methyltryptamine and DMT in the proportions approx. 2:3 (Fitzgerald & Sioumis 1965). A. simplicifolia also contains DMT (Poupat et al. 1976). Seeds of several acacia species are available from ..Of the jungle. Genus: Desmanthus Species: illinoensis "Illinois Bundleflower" Thompson et al. report that the root bark of this North American perennial shrub contains 0.34% DMT and 0.11% N-methyltryptamine. The bark accounts for about a half of the total weight of the roots. The plant should be resistant to cold and draught and easy to grow. ..Of the Jungle sells D. illinoensis seeds and dried roots (seed packet $3, 7 grams $10, oz $25; roots 4 oz $15, pound $50). Seeds are also available from more main-stream mail-order houses. Genus: Mimosa Species: tenuiflora (== hostilis) "tepescohuite" verrucosa The roots of M. hostilis, which is not the common houseplant M. pudica ("sensitive plant"), contain 0.57% DMT and are used by Indians of Pernambuso State in Brazil as part of their Yurema cult (Pachter et al. 1959, Schultes 1977, Meckes-Lozoya et al. 1990). Bark of M. verrucosa also contains DMT (Smith 1977). Family: Malpighiaceae Genus: Banisteriopsis Species: argentea rusbyana Natives of western Amazon add DMT-containing leaves of the vine B. rusbyana to a drink made from B. caapi, which contains beta-carbolines harmine and harmaline, to heighten and lengthen the visions (Schultes 1977, Smith 1977). Family: Myristicaceae Genus: Virola Species: calophylla calophylloidea rufula sebifera theiodora The bark resin of these trees is used to prepare hallucinogenic snuffs in northwestern Brazil by boiling, drying and pulverizing it. Sometimes leaves of a Justicia are added. The snuff acts rapidly and violently, "effects include excitement, numbness of the limbs, twitching of facial muscles, nausea, hallucinations, and finally a deep sleep; macroscopia is frequent and enters into Waika beliefs about the spirits resident in the drug." Snuffs made from V. theiodora bark contain up to 11% 5-MeO-DMT and DMT. Also leaves, roots and flowers contain DMT. Amazonian Colombia natives roll small pellets of boiled resin in a evaporated filtrate of bark ashes of Gustavia Poeppigiana and ingest them to bring on a rapid intoxication (Smith 1977, Schultes 1977). Family: Pandanaceae Genus: Pandanus "Screw pine" DMT has been isolated from Pandanus nuts growing in New Guinea (Barrau 1958, 1962). Family: Poaceae Genus: Arundo Species: donax Leaves, flowers and rhizomes contain DMT, bufotenine and related compounds (Ghosal et al. 1972). Genus: Phalaris Species: aquatica (tuberosa) arundinacea Leaves of P. arundinacea and leaves and seedlings of P. aquatica contain DMT, 5-MeO-DMT and related compounds (Smith 1977). P. arundinacea plants are available from ..Of the jungle for $15. Family: Rubiaceae Genus: Psychotria Species: carthaginensis viridis (psychotriaefolia) Psychotria leaves are added to a hallucinogenic drink prepared from Banisteriopsis caapi and B. rusbyana (which contain beta-carbolines) to strengthen and lengthen the effects in western Amazon. P. carthaginensis and P. viridis both contain DMT (Rivier, 1972). 5 seeds of P. viridis cost $10 from ..Of the jungle. Family: Rutaceae Genus: Dictyoloma Species: incanescens Bark contains 0.04% 5-MeO-DMT (Pachter et al. 1959). Genus: Vepris Species: ampody Contains DMT (Smith 1977). References Arora, D. 1986. Mushrooms Demystified: A Comprehensive Guide to the Fleshy Fungi. Ten Speed Press, Berkley. Arthur, H.R., Loo, S.N. & Lamberton, J.A. 1967. 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Indolealkylamines of Desmanthus illinoensis and Their Growth Inhibition Activity. J Agric. Food Chem. 35, 361-365. -- Petrus.Pennanen@helsinki.fi * Everything is perfect forever Michael from Melbourne * Ditto --- Paul Walsh pwal1@eng3.eng.monash.edu.au