484 lines
22 KiB
Plaintext
484 lines
22 KiB
Plaintext
Hello Lamont! Can you put this in the archives:
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TRYPTAMINE CARRIERS
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===================
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by Petrus Pennanen (ppennane@cc.helsinki.fi) Last update Apr 7 1993
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Thanks to many individuals for help in putting this together!
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If you know sources of tryptamines that are not mentioned here please mail me.
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ORALLY AND PARENTERALLY ACTIVE PSYCHOTROPIC TRYPTAMINE DERIVATIVES
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Based on McKenna & Towers 1984
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R4 R1
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R5 // \ /\ N
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\// \ ____/ \ / \
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| || || | R2
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\\ /\ / R3
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\\ / \ /
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N
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H Dosage Route
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Name of Compound R1 R2 R3 R4 R5 (mg) Oral/Par.
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-----------------------------------------------------------------------------
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tryptamine H H H H H 100 *1 par/oral?
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DMT (dimethyltryptamine) CH3 CH3 H H H 60 par
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DET C2H5 C2H5 H H H 60 par/oral
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DPT n-prop n-prop H H H 60 par/oral
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DAT C3H5 C3H5 H H H 30 par/oral
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DIPT i-prop i-prop H H H 30 oral
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5-MeO-DIPT i-prop i-prop H H OCH3 12 oral
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5-MeO-DMT CH3 CH3 H H OCH3 6 par
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psilocin CH3 CH3 H OH H 12 *2 oral
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CZ-74 C2H5 C2H5 H OH H 15 *2 oral
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serotonin H H H H OH 100 *3 oral
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bufotenine CH3 CH3 H H OH 16 *4 par
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IT-290 H H CH3 H H 30 oral
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4-hydroxy-alfa-methyl-
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tryptamine H H CH3 OH H 20 *3 oral
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MP-809 H H CH3 H CH3 60 *5 oral
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5-fluoro-alfa-methyl-
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tryptamine H H CH3 H F 25 *6 oral
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5-methoxy-alfa-methyl-
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tryptamine H H CH3 H OCH3 3 oral
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4-hydroxy-diisopropyl-
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tryptamine i-prop i-prop H OH H 12 *6 oral
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4-hydroxy-N-isopropyl,
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N-methyl-tryptamine i-prop CH3 H OH H 6 *6 oral
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N-t-butyl-tryptamine H t-butylH H H ? *7 par?
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3-(2-(2,5-dimethyl
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pyrrolyl)ethyl)-indole H H H ? ?
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5-alfa-DMT CH3 CH3 CH3 H H ? ?
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-----------------------------------------------------------------------------
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Data compiled from Kantor, et al. 1980; Shulgin 1976,1982; Shulgin&Carter 1980
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*1 Autonomic symptoms; little central activity.
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*2 The phosphate esters are psilocybin and CEY-19, respectively; both are
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stoichiometrically equivalent to the 4-hydroxy isomers.
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*3 Cardiovascular and autonomic symptoms; little central activity.
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*4 A pressor amine rather than a hallucinogen in man.
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*5 An antidepressant rather than a hallucinogen in man.
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*6 Based on anonymous reports in the lay press. No clinical studies have been
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published.
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*7 No oral activity with doses up to 20 mg, may be parenterally active.
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Other potentially psychedelic tryptamines include
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6-fluoro-alfa-methyltryptamine, 7-methyltryptamine, 5-methyltryptamine,
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5-fluorotryptamine, 6-fluorotryptamine and 5- and 6-fluorotryptophans.
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MAO Inhibitors and Tryptamines
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Monoamine oxidase (MAO) is the primary inactivation pathway of most
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tryptamines. Because of this, inhibitors of the MAO enzyme (MAOIs) can be
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used to potentiate the effects of tryptamines and to make DMT and 5-MeO-DMT
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orally active.
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MAO inhibitors fall into two classes: Irreversible and reversible MAOIs.
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Irreversible MAOIs (e.g. the hydrazides iproniazid and phenelzine) bind
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permanently to the enzyme and cause MAO inhibition lasting 1-2 weeks after
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ingestion. They are used clinically to treat depression. Reversible MAOIs,
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such as moclobemid and the beta-carbolines harmine and harmaline, are
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effective for much shorter time, maybe up to 24 hours. Reversible MAOIs are
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not widely used clinically, but recreational drug users around the world
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prefer them despite the lack of scientific studies about their effects in
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humans.
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Natives of Amazon have traditionally combined Banisteriopsis caapi vine,
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which contains harmine, harmaline and related beta-carbolines, with DMT-
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containing plants to make an orally active brew called ayahuasca. Other
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plants containing harmine and/or harmaline can be substituted for B.
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caapi. The usual 'North-American ayahuasca' consists of Peganum harmala
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seeds and Desmanthus illinoensis roots, and in Australian 'acaciahuasca'
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leaves of Acacia complanata are combined with material from DMT-containing
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acacias (the effectivity of this mixture hasn't been confirmed). MAOIs
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have also been used to potentiate the effects of mushrooms containing
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psilocybin. Terence McKenna has mentioned chocolate being a weak MAOI, which
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could be a reason for the popular habit of ingesting mushrooms with cocoa.
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Peganum harmala (Syrian rue) seeds are the most concentrated natural source
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of harmine and harmaline - about 3% of their weight consists of these
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alkaloids. Banisteriopsis caapi has been found to contain from 0.18% to
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1.36% beta-carbolines, with the concentration of harmine being from 0.057%
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to 0.635% (McKenna et al. 1984). According to anecdotal reports one gram
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of P. harmala seeds ingested inhibits MAO enough to make DMT orally active.
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Harmine and harmaline are hallucinogenic on their own with doses
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starting from around 300 mg (Naranjo 1967). They have little emotional
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or 'psychedelic' effects, but produce strong visual hallucinations. Because of
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this the natives of Amazon often add larger amounts (75-100 cm of stem per
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dose) of B. caapi to ayahuasca brew than is needed for MAO inhibition
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(Luna 1984).
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There are significant dangers in using MAO inhibitors. MAOIs potentiate
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the cardiovascular effects of tyramine and other monoamines found in
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foods. Ingestion of aged cheese, beer, wine, pickled herring, chicken liver,
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yeast, large amounts of coffee, citrus fruits, canned figs, broad beans,
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chocolate or cream while MAO is inhibited can cause a hypertensive
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crisis including a dangerous rise in blood pressure. Effects of
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amphetamines, general anaesthetics, sedatives, anti-histamines, alcohol,
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potent analgesics and anticholinergic and antidepressant agents are
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prolonged and intensified. Overdosage of MAOIs by themselves is also
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possible with effects including hyperreflexia and convulsions.
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Self-Synthesis of DMT Derivatives
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Tryptamine derivatives and beta-Carbolines have been detected as
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endogenous metabolites in mammals, including humans. Methyl transferases
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that catalyze the synthesis of tryptamines, including DMT, 5-MeO-DMT and
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bufotenine, are found in human lung, brain, cerebrospinal fluid, liver
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and heart (McKenna & Towers 1984). In the pineal gland MAO is the primary
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inactivation pathway of serotonin, a neurotransmitter synthesized from the
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amino acid tryptophan. If MAO is blocked by harmine, harmaline or other MAO
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inhibitors serotonin can be converted by the methyltransferase enzymes
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HIOMT and INMT into psychedelic tryptamines (serotonin --(HIOMT)-->
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5-MeO-trypt. --(2*INMT)--> 5-MeO-DMT).
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So, ingesting l-tryptophan to increase serotonin levels, a candy bar to
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increase the amount of tryptophan getting to your brain and natural
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plant material containing 25-50 mg harmine/harmaline to block MAO, all at the
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same time, is supposed to cause your pineal gland to synthesize substantial
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amounts of 5-MeO-DMT (Most 1986). This is extremely dangerous for persons
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with existing amine imbalance or schizophrenia. For normal, healthy people
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possible consequences are bad.
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A potent inhibitor of INMT, which is a necessary enzyme for the synthesis
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of DMT and 5-MeO-DMT, is found in particularly high concentrations in the
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pineal gland. A bypassing or inhibition of the synthesis of this inhibitor
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might be responsible for trances and other psychedelic states achieved
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"without drugs" (Strassman 1990). See Strassman's article for more info and
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speculation about the pineal gland.
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Psychedelic Toads
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Bufotenine and related 5-hydroxy-indolethylamines are common constituents
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of venoms of the genera Hyla, Leptodactylus, Rana and Bufo. Bufotenine
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is not psychedelic in reasonable doses (with larger doses there are
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dangerous physiological side effects), but the skin of one species, Bufo
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alvarius, contains 50-160 mg 5-MeO-DMT/g of skin (Daly & Witkop 1971).
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It's the only Bufo species known to contain a hallucinogenic tryptamine
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(McKenna & Towers 1984). Most (1984) gives instructions for collecting
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and drying the venom:
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Fresh venom can easily be collected without harm to the toad. Use a flat
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glass plate or any other smooth, nonporous surface at least 12-inches
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square. Hold the toad in front of the plate, which is fixed in a vertical
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position. In this manner, the venom can be collected on the glass plate,
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free of dirt and liquid released when the toad is handled.
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When you are ready to begin, hold the toad firmly with one hand and, with
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the thumb and forefinger of your other hand, squeeze near the base of the
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gland until the venom squirts out of the pores and onto the glass plate. Use
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this method to systematically collect the venom from each of the toad's
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granular glands: those on the forearm, those on the tibia and femur of the
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hind leg, and, of course, the parotoids on the neck. Each gland can be
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squeezed a second time for an additional yield of venom if you allow the toad
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a one-hour rest preiod. After this the glands are empty and require four to
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to six weeks for regeneration.
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The venom is viscous and milky-white in color when first squeezed from the
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glands. It begins to dry within minutes and acquires the color and texture
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of rubber cement. Scrape the venom from the glass plate, dry it thoroughly,
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and store it in an airtight container until you are ready to smoke it.
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Davis and Weil (1992) smoked the venom and described what happened:
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In comparison to the pure compounds the toad venom appears longer lasting
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and, because one does not completely lose contact with reality, far more
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pleasant, even sensual. Shortly after inhalation I experienced warm flushing
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sensations, a sense of wonder and well-being, strong auditory hallucinations,
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which included an insect-cicada sound that ran across my mind and seemed to
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link my body to the earth. Though I was indoors, there was a sense of the
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feel of the earth, the dry desert soil passing through my fingers, the stars
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at midday, the scent of cactus and sage, the feel of dry leaves through hands.
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Strong visual hallucinations in orblike brilliance, diamond patterns that
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undulated across my visual field. The experience was in every sense pleasant,
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with no disturbing physical symptoms, no nausea, perhaps a slight sense of
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increased heart rate. Warm waves coursed up and down my body. The effects
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lasted only a few minutes but a pleasant afterglow continued for almost an
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hour. (Wade Davis, personal observation, January 12, 1991)
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Profound alteration of consciousness within a few seconds of exhaling. I
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relax into a deep, peaceful interior awareness. There is nothing scary about
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the effects and no sense of toxicity. I try to describe my feelings but am
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unable to talk for the first five minutes and then only with some difficulty.
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This is a powerful psychoactive drug, one that I think would appear to most
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people who like the effects of hallucinogens. For the next hour I feel slow
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and velvety, with a slight pressure in my head. No long-lasting effects to
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report. (Andrew T. Weil, personal observation, January 12, 1991)
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The Plants
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Family: Acanthaceae
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Genus: Justicia
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Species: pectoralis (var. stenophylla)
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Waikas of Orinoco headwaters in Venezuela add dried and pulverized
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leaves of this herb to their Virola-snuff. Intensely aromatic smelling
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leaves probably contain tryptamines (Schultes 1977). Plants are available
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from ..Of the jungle (PO Box 1801 sebastopol CA 95473) for $35.
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Family: Agaricaceae
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Genus: Lepiota
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Species: peele "Peele's Lepiota"
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This recently discovered mushroom is supposed to contain a legal tryptamine,
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which produces a trip with less physical symptoms and better ability of
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logical thinking than psilocin/psilocybin. Florida Mycology Research Center
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(PO Box 8104 Pensacola Florida 32505) sells spores ($10) and cultures ($112).
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Genus: Psilocybe
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These are the psilocin and psilocybin carrying mushrooms, which have
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their own section in the Natural Highs FAQ.
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Family: Aizoaceae
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Genus: Delosperma
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Contains DMT and N-methyltryptamine (see Smith 1977 for refs).
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Family: Apocynaceae
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Genus: Prestonia
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Species: amazonica?
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Contains DMT (Smith 1977).
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Family: Cactaceae
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Genus: Echinocereus
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Species: triglochidiatus
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salm-dyckianus
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These cacti growing in Mexico are known to Tarahumare Indians as peyote or
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hikuli and used in their festivals. E. triglochidiatus contains a tryptamine
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derivative, possibly 5-MeO-DMT (Bye 1979). E. salm-dyckianus is also supposed
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to contain tryptamines according to Horus Botanicals catalog 1992.
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Genus: Trichocereus
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Species: terscheckii "Cardon grande"
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DMT has been isolated from this species growing in North-Western
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Argentina (Schultes & Hofmann 1979 p. 58).
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Family: Gramineae
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Genus: Arundo
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Species: donax
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Leaves, flowers and rhizomes contain DMT, Bufotenine and related compounds
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(Ghosal et al. 1972).
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Genus: Phalaris
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Species: arundinacea
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tuberosa
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Leaves of P. arundinacea and leaves and seedlings of P. tuberosa
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contain DMT, 5-MeO-DMT and related compounds (Smith 1977). P.
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arundinacea plants are available from ..Of the jungle for $15.
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Family: Leguminosae
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Genus: Acacia
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Species: confusa
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jurema
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maidenii
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phlebophylla
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polycantha subsp. campylacantha
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niopo
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nubica
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senegal
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others
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Dried A. confusa stems contain 0.04% N-methyltryptamine and 0.02% DMT
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(Arthur et al. 1967). The dried leaves of A. phlebophylla contain 0.3% DMT
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(Rovelli & Vaughan 1967). The bark of A. maidenii contains 0.6% of
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N-methyltryptamine and DMT in the proportions approx. 2:3 (Fitzgerald
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& Sioumis 1965). Smith (1977) and Schultes & Hofmann (1980 pp. 142 and 155)
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mention other species.
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Seeds of several acacia species are available from ..Of the jungle.
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Genus: Anadenanthera (Piptadenia)
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species: peregrina
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colubrina
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Black beans from these trees are toasted, pulverized and mixed with ashes
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or calcined shells to make psychedelic snuff called yopo by Indians in
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Orinoco basin in Colombia, Venezuela and possibly in southern part of
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Brasilian Amazon. Yopo is blown into the nostrils through bamboo tubes
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or snuffed by birdbone tubes. The trees grow in open plain areas, and
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leaves, bark and seeds contain DMT, 5-MeO-DMT and related compounds
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(Schultes 1976,1977; Pachter et al. 1959).
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Genus: Desmanthus
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Species: illinoensis "Illinois Bundleflower"
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Thompson et al. report that the root bark of this North American perennial
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shrub contains 0.34% DMT and 0.11% N-methyltryptamine. The bark accounts
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for about a half of the total weight of the roots. The plant should be
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resistant to cold and draught and easy to grow. ..Of the Jungle sells D.
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illinoensis seeds and dried roots (seed packet $3, 7 grams $10, oz $25;
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roots 4 oz $15, pound $50). Seeds are also available from more main-stream
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mail-order houses.
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Genus: Desmodium
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Species: gangetium
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gyrans
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pulchellum
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tiliaefolium
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triflorum
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Leaves, root, stem and seeds contain DMT and 0.06% 5-MeO-DMT of wet weight
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(Banerjee & Ghosal 1968).
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Genus: Lespedeza
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Species: bicolor
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Leaves and root contain DMT and 5-MeO-DMT (Smith 1977). Seeds of this hardy
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perennial shrub are available from ..Of the jungle for $5.
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Genus: Mimosa
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Species: tenuiflora (== hostilis) "tepescohuite"
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verrucosa
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The roots of M. hostilis, which is not the common houseplant M. pudica
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("sensitive plant"), contain 0.57% DMT and are used by Indians of Pernambuso
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State in Brazil as part of their Yurema cult (Pachter et al. 1959, Schultes
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1977, Meckes-Lozoya et al. 1990). Bark of M. verrucosa also contains DMT
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(Smith 1977).
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Genus: Mucuna
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Species: pruriens
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Leaves, stem and fruit of this jungle vine contains DMT and 5-MeO-DMT
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(Smith 1977). Seeds are available from ..Of the jungle for $5.
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Genus: Petalostylis
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species: labicheoides
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Leaves and stem contain 0.4-0.5% tryptamine, DMT and other alkaloids
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(Johns et al. 1966).
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Family: Malpighiaceae
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Genus: Banisteriopsis
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Species: rusbyana
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argentea
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Natives of western Amazon add DMT-containing leaves of the vine B. rusbyana
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to a drink made from B. caapi, which contains beta-carbolines harmine and
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harmaline, to heighten and lengthen the visions (Schultes 1977, Smith 1977).
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Family: Myristicaceae
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Genus: Virola
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Species: calophylla
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calophylloidea
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rufula
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sebifera
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theiodora
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The bark resin of these trees is used to prepare hallucinogenic snuffs
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in northwestern Brazil by boiling, drying and pulverizing it. Sometimes
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leaves of a Justicia are added. The snuff acts rapidly and violently,
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"effects include excitement, numbness of the limbs, twitching of facial
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muscles, nausea, hallucinations, and finally a deep sleep; macroscopia is
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frequent and enters into Waika beliefs about the spirits resident in the
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drug." Snuffs made from V. theiodora bark contain up to 11% 5-MeO-DMT and
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DMT. Also leaves, roots and flowers contain DMT.
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Amazonian Colombia natives roll small pellets of boiled resin in a
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evaporated filtrate of bark ashes of Gustavia Poeppigiana and ingest
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them to bring on a rapid intoxication (Smith 1977, Schultes 1977).
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Family: Pandanaceae
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Genus: Pandanus "Screw pine"
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DMT has been isolated from Pandanus nuts growing in New Guinea (Barrau 1958,
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1962).
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Family: Rubiaceae
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Genus: Psychotria
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Species: viridis (psychotriaefolia)
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Psychotria leaves are added to a hallucinogenic drink prepared from
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Banisteriopsis caapi and B. rusbyana (which contain beta-carbolines) to
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strengthen and lengthen the effects in western Amazon. P. viridis
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contains DMT (Schultes 1977). 5 seeds $10 from ..Of the jungle.
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Family: Rutaceae
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Genus: Dictyoloma
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Species: incanescens
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Bark contains 0.04% 5-MeO-DMT (Pachter et al. 1959).
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Genus: Vepris
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Species: ampody
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Contains DMT (Smith 1977).
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References
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Arthur, H.R., Loo, S.N. & Lamberton, J.A. 1967. Nb-methylated tryptamines
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and other constituents of Acacia confusa Merr. of Hong Kong. Aust. J
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Chem. 20, 811.
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Banerjee, P.K. & Ghosal, S. 1968. Simple indole bases of Desmodium gangeticum.
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Aust. J Chem. 22, 275.
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Barrau, J. 1958. Nouvelles observations au sujet des plantes hallucinogenes
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d'usage autochtone en Nouvelle-Guinee. J Agric. Trop. Bot. Appl. 5, 377-378.
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Barrau, J. 1962. Observations et travaux recents sur les vegetaux
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hallucinogenes de la Nouvelle-Guinee. J Agric. Trop. Bot. Appl. 9, 245-249.
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Bye, R.A. 1979. Hallucinogenic plants of the Tarahumara. J Ethnopharmacology
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1, 23-48.
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Daly, J.W. & Witkop, B. 1971. Chemistry and pharmacology of frog venoms.
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In: Venomous animals and their venoms. Vol II. New York: Academic Press.
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Davis, W. & Weil, A.T. 1992. Identity of a New World Psychoactive Toad.
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Ancient Mesoamerica 3 (1992) 5, 51-59.
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Fitzgerald, J.S. & Sioumis, A.A. 1965. Alkaloids of Australian
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--
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Petrus.Pennanen@helsinki.fi Everything is perfect forever.
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I love you.
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