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From: ppennane@klaava.Helsinki.FI (Petrus Pennanen)
Newsgroups: alt.drugs
Subject: Tryptamine FAQ
Date: 24 Mar 1994 16:43:24 +0200
Message-ID: <2ms8uc$4jn@klaava.Helsinki.FI>
TRYPTAMINE CARRIERS Last update Mar 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
me or Michael.
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 moclobemid and the beta-carbolines harmine and harmaline, are
effective for much shorter time, maybe up to 24 hours. Reversible MAOIs are
not widely used clinically, but recreational drug users around the world
prefer them despite the lack of scientific studies about their effects in
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: Conocybe
Species: cyanopus
smithii
C. cyanopus (Benedict et al. 1962) and in C. smithii (Natural Highs FAQ)
contain psilocybin and psilocin.
Family: Coprinaceae
Genus: Copelandia
Species: cyanescens
Contains psilocin and psilocybin (Schultes & Hofmann 1979 p. 40).
Genus: Panaeolus
Species: ater
campanulatus
foenisecii
papilionaceus
retirugis
separatus
sphinctrinus
subbalteatus
Several Panaeolus species contain psilocin and psilocybin. For P. ater refer
to Bresinsky et al. (1990), for P. foenisecii (Robbers et al. 1962), for
P. papilionaceus (Gurevich et al. 1992), for P. retirugis (Fiussello et al.
1971/72), for P. separatus (Miller Jr. 1972), for P. sphinctrinus (Schultes
& Hofmann 1979 p. 52) and for P. subbalteatus (Gurevich 1993).
Family: Cortinariaceae
Genus: Gymnopilus
Species: spectabilis
purpuratus
Contain psilocin and psilocybin, for G. spectablis refer to Hatfield et al.
(1978) 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: Lepiotaceae
Genus: Lepiota
Species: peele "Peele's Lepiota"
This recently discovered mushroom is supposed to contain a legal tryptamine,
which produces a trip with less physical symptoms and better ability of
logical thinking than psilocin or psilocybin. Florida Mycology Research Center
(PO Box 8104 Pensacola Florida 32505) sells spores ($10), cultures ($112)
and information leaflets about L. peele.
Family: Pluteaceae
Genus: Pluteus
Species: salicinus
nigroviridis
Both P. salicinus (Saupe 1981) and P. nigroviridis (Christiansen et al. 1984)
contain psilocin and psilocybin.
Family: Strophariaceae
Genus: Psilocybe
There are at least 75 mushroom species in this genera that contain psilocin
and psilocybin (Guzman 1983).
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: triglochidiatus
salm-dyckianus
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
pulchellum
tiliaefolium
triflorum
Leaves, root, stem and seeds contain DMT and 0.06% 5-MeO-DMT of wet weight
(Banerjee & Ghosal 1968).
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.
Family: Mimosaceae
Genus: Anadenanthera
species: peregrina
colubrina
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
phlebophylla
polycantha subsp. campylacantha
niopo
nubica
senegal
others
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). Smith (1977) and Schultes & Hofmann (1980 pp. 142 and 155)
mention other species.
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: rusbyana
argentea
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: 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. viridis
contains DMT (Schultes 1977). 5 seeds $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
Arthur, H.R., Loo, S.N. & Lamberton, J.A. 1967. Nb-methylated tryptamines
and other constituents of Acacia confusa Merr. of Hong Kong. Aust. J
Chem. 20, 811.
Banerjee, P.K. & Ghosal, S. 1968. Simple indole bases of Desmodium gangeticum.
Aust. J Chem. 22, 275.
Barrau, J. 1958. Nouvelles observations au sujet des plantes hallucinogenes
d'usage autochtone en Nouvelle-Guinee. J Agric. Trop. Bot. Appl. 5, 377-378.
Barrau, J. 1962. Observations et travaux recents sur les vegetaux
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Benedict, R.G., Brady, L.R., Smith, A.H. & Tyler, V.E. 1962. Occurrence of
psilocybin ans psilocin in certain Conocybe and Psilocybe species. Lloydia
25, 156-159.
Bresinsky, A. & Besl, H. 1990. A Colour Atlas of Poisonous Fungi. Wolfe
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Christiansen, A.L., Rasmussen, K.E. & Hoeiland, K. 1984. Detection of
psilocybin and psilocin in Norwegian species of Pluteus and Conocybe.
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Crouch, I.J., Smith M.T., Van Staden J., Lewis, M.J. & Hoad, G.V. 1992.
Identification of auxins in a commercial seaweed concentrate. J Plant
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Robbers, J.E., Tyler, V.E. & Ola'h, G.M. 1969. Additional evidence supporting
the occurrence of psilocybin in Panaeolus foenisecii. Lloydia 32, 399-400.
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20, 1299.
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Psychedelic Drugs Vol 8 No 1 7-25.
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