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Based onMcKenna & Towers 1984

Molecular Schematic
MAO Inhibitors and Tryptamines
Synthesis of DMT Derivatives
Psychedelic Toads
The Fungi
The Plants
References

Data compiled fromKantor, et al. 1980;Shulgin 1976,1982; Shulgin&Carter; 1980
Name of CompoundR1R2R3R4R5Dosage
(mg)		Route
Oral/Par.
tryptamineHHHHH100 *1par/oral?
DMT (dimethyltryptamine)CH3CH3HHH60par
DETC2H5C2H5HHH60par/oral
DPTn-propn-propHHH60par/oral
DATC3H5C3H5HHH30par/oral
DIPTi-propi-propHHH30oral
5-MeO-DIPTi-propi-propHHOCH312oral
5-MeO-DMTCH3CH3HHOCH36par
psilocinCH3CH3HOHH12 *2oral
CZ-74C2H5C2H5HOHH15 *2oral
serotoninHHHHOH100 *3oral
bufotenineCH3CH3HHOH16 *4par
IT-290HHCH3HH30oral
4-hydroxy-alfa-methyl-tryptamineHHCH3OHH20 *3oral
MP-809HHCH3HCH360 *5oral
5-fluoro-alfa-methyl-tryptamineHHCH3HF25 *6oral
5-methoxy-alfa-methyl-tryptamineHHCH3HOCH33oral
4-hydroxy-diisopropyl-tryptaminei-propi-propHOHH12 *6oral
4-hydroxy-N-isopropyl,
N-methyl-tryptamine		i-propCH3HOHH6 *6oral
N-t-butyl-tryptamineHt-butylHHH?*7par?
3-(2-(2,5-dimethylpyrrolyl)
ethyl)-indole		HHH????
5-alfa-DMTCH3CH3CH3HH??
Other potentially psychedelic tryptamines include:
6-fluoro-alfa-methyltryptamine, 7-methyltryptamine, 5-methyltryptamine
5-fluorotryptamine, 6-fluorotryptamine and 5- and 6-fluorotryptophans.

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MAO Inhibitors and Tryptamines

Monoamine oxidase (MAO) is the primary inactivation pathway of mosttryptamines. Because of this, inhibitors of the MAO enzyme (MAOIs) can beused to potentiate the effects of tryptamines and to make DMT and 5-MeO-DMTorally active.

MAO inhibitors fall into two classes: Irreversible and reversible MAOIs.In addition they can inhibit either or both of the two types of the MAOenzyme, MAO-A and MAO-B which are associated with serotonergic anddopaminergic neurons respectively. 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 calledayahuasca. Other plants containing harmine and/or harmaline can be substituted for B. caapi. The usual 'North American ayahuasca' consists ofPeganum harmalaseeds and Desmanthus illinoensis roots, and in Australian 'acaciahuasca' leaves of Acacia complanata are combined with material fromDMT-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 sourceof harmine and harmaline - about 3% of their weight consists of thesealkaloids. 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 dosesstarting from around 300 mg (Naranjo 1967), but often cause physicalside-effects such as nausea and tremors in this dose range. 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. Most MAOIs potentiate the cardiovascular effects of tyramine and other monoamines found infoods. 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 hypertensivecrisis including a dangerous rise in blood pressure. Effects ofamphetamines, general anaesthetics, sedatives, anti-histamines, alcohol,potent analgesics and anticholinergic and antidepressant agents areprolonged and intensified. Overdosage of MAOIs by themselves is alsopossible with effects including hyperreflexia and convulsions.

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Synthesis of DMT Derivatives

Tryptamine derivatives and beta-Carbolines have been detected asendogenous metabolites in mammals, including humans. Methyl transferasesthat catalyze the synthesis of tryptamines, including DMT, 5-MeO-DMT andbufotenine, are found in human lung, brain, cerebrospinal fluid, liverand 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 naturalplant material containing 25-50 mg harmine/harmaline to block MAO, all at thesame time, might cause your pineal gland to synthesize substantial amounts of5-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 synthesisof DMT and 5-MeO-DMT, is found in particularly high concentrations in thepineal gland. A bypassing or inhibition of the synthesis of this inhibitormight 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.

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Psychedelic Toads

bufo toad imageBufotenine and related 5-hydroxy-indolethylamines are common constituentsof venoms of the genera Hyla, Leptodactylus, Rana and Bufo. Bufotenineis not psychedelic in reasonable doses (with larger doses there aredangerous physiological side effects), but the skin of one species, Bufoalvarius, 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, theparotids 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 appeal 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).

Other animals contain DMT such as the gorgonian Paramuricea chamaeleon (Cimino & De Stefano, 1978).

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a poisonous mushroom, don't eat this one!

he Fungi

bemushroomed
Contains psilocybin (Koike et al. 1981).
C. cyanopus (Benedict et al. 1962) and 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).
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).
P. foenisecii contains psilocybin (Robbers et al. 1969).
Several Panaeolus species contain psilocybin. For P. antillarum refer to Allen et al. (1991), for P. ater refer toBresinsky 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).
Contains psilocybin (Koike et al. 1981) and psilocin (Ohenoja et al. 1987).
Contains psilocybin and psilocin (Besl, 1993).
Many Gymnopilus contain psilocybin, for G. aeruginosus, G. luteus, G. spectabilis, G. validipes and G.viridans refer toHatfield et al. (1978). For G. liquiritiae (Koike, 1981) and for G. purpuratus (Gartz 1991).
These contain psilocin and psilocybin, for P. aeruginascens refer toHaeselbarth et al. (1985) and for the othersStijve et al. (1985).
This mushrooms was claimed by Peele of Florida Mycology Research Center (PO Box 8104 Pensacola Florida 32505) to contain a legal tryptamine,which produces a trip with less physical symptoms and better ability oflogical thinking than psilocin or psilocybin. Bioassay results didn't findpsychoactivity (Akers 1992).
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.
These contain psilocybin.
This contains psilocybin.
Psilocybe cubensisThere are at least 75 mushroom species in this genera that contain psilocin and psilocybin inGuzman 1983, and there are several more recently discovered species such as P. aucklandii (Guzman et al. 1993), P. samuiensis (Guzman et al. 1991) and P. antioquensis, P. beliconiae, P. guatapensis and P. subacutipilea (Guzman et al. 1994). 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).

Images of Psilocybe cyanescens, cyanofibrillosa, azurescens, semilanceata, pelliculosa, silvatica can be seen atA Gallery of Psilocybe Mushrooms

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a plant

The Plants

J.pectoralisWaikas of Orinoco headwaters in Venezuela add dried and pulverizedleaves of this herb to their Virola-snuff. Intensely aromatic smelling leaves probably contain tryptamines (Schultes 1977). Plants are available from fromHoti Products or..Of the jungle.
Contains DMT and N-methyltryptamine (Rivier & Pilet, 1971).
Crouch et al. (1992) reported finding DMT in brown seaweed extract sold asKelpak and intended to be used as a plant fertilizer. However, subsequentanalysis byJ. Gartz suggests none is present.
May contain DMT but the specimen used may have been misidentified (Smith 1977).
These cacti growing in Mexico are known to Tarahumare Indians as peyote orhikuli and used in their festivals. E. triglochidiatus contains a tryptaminederivative, possibly 5-MeO-DMT (Bye 1979). E. salm-dyckianus is also supposed to contain tryptamines according to Horus Botanicals catalog 1992.
DMT has been isolated from this species growing in North-WesternArgentina (Schultes & Hofmann 1979 p. 58).
Leaves and stem contain 0.4-0.5% tryptamine, DMT and other alkaloids (Johns et al. 1966).
Leaves, root, stem and seeds contain DMT and 0.06% 5-MeO-DMT of wet weight (Banerjee & Ghosal 1969).
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.
Leaves, stem and fruit of this jungle vine contains DMT and 5-MeO-DMT (Ghosal et al., 1971). Seeds are available from ..Of the jungle for $5.
Dried plant material produced 0.2% 5-MeO-DMT and small amounts of DMT (Ghosal & Mukherjee 1966).
Black beans from these trees are toasted, pulverized and mixed with ashesor 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 tubesor snuffed by birdbone tubes. The trees grow in open plain areas, and leaves, bark and seeds contain DMT, 5-MeO-DMT and related compounds (Schultes1976,1977;Pachter et al. 1959; Phytochem 11, 737).
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. simplex also contains DMT (Poupat et al. 1976).Several Sudanese species have DMT (Wahba & Elkheir, 1975). Seeds of severalacacia species are available from ..Of the jungle.
Thompson et al. report that the root bark of this North American perennialshrub contains 0.34% DMT and 0.11% N-methyltryptamine. The bark accountsfor about a half of the total weight of the roots. The plant should beresistant 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-streammail-order houses.
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). M. scabrella contains DMT and N-methyltryptamine (De Moraes et al., 1990). Bark of M. verrucosa also contains DMT (Smith 1977).
Contains DMT (Leboeuf et al., 1977).
Both contain DMT (Smith 1977).
Natives of western Amazon add DMT- and N-methyltryptamine containing leaves of the vine D. cabrerana to a drink made from Banisteriopsis caapi, which contains beta-carbolines harmine and harmaline, to heighten and lengthen the visions (Schultes 1977,Smith 1977). D. cabrerana is also known as Banisteriopsis rusbyana.
Contains 5-MeO-DMT as well as a beta-carboline (Jossang et al. 1991).
The bark contains 5-MeO-DMT (Holmstedt et al. 1980).
The bark resin of these trees is used to prepare hallucinogenic snuffsin northwestern Brazil by boiling, drying and pulverizing it. Sometimesleaves of a Justicia are added. The snuff acts rapidly and violently,"effects include excitement, numbness of the limbs, twitching of facialmuscles, nausea, hallucinations, and finally a deep sleep; macroscopia isfrequent and enters into Waika beliefs about the spirits resident in thedrug." 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 aevaporated filtrate of bark ashes of Gustavia Poeppigiana and ingestthem to bring on a rapid intoxication (Smith 1977,Schultes 1977).

DMT has been isolated from Pandanus nuts growing in New Guinea (Barrau 1958, 1962).
Leaves, flowers and rhizomes contain DMT, bufotenine and related compounds(Ghosal et al. 1972).
phalarisLeaves 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.
Rhizomes contain DMT (Wassel et al. 1985).
P.viridisPsychotria leaves are added to a hallucinogenic drink prepared fromBanisteriopsis caapi and B. rusbyana (which contain beta-carbolines) tostrengthen and lengthen the effects in western Amazon. P. carthaginensis and P. viridis both contain DMT (Rivier, 1972). 5 seeds of P. viridiscost $10 from ..Of the jungle.
Bark contains 0.04% 5-MeO-DMT (Pachter et al. 1959).
Contains DMT (Abu Zarga, 1986).
Contains 5-MeO-DMT as well as 5-MeO-DMT-Oxide and a beta-carboline (Skaltsounis et al. 1983).
The leaves and branches contains up to 0.2% DMT (Kan-Fan 1970).
Contains DMT (Grina et al., 1982).

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Petrus.Pennanen@helsinki.fi * Everything is perfect forever
Michael from Melbourne * Ditto

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