From: ppennane@klaava.Helsinki.FI (Petrus Pennanen)
Newsgroups: alt.drugs
Subject: Psychedelic Tryptamines
Keywords: anonymous
Date: 13 Nov 92 11:14:04 GMT
Organization: University of Helsinki

In article <1992Nov12.064323.7187@u.washington.edu> ap.6396@cupid.sai.com writes:
>The subject of DMT came up, and in a previous post it was mentioned that
>it was available in some plants and could be extracted.  Does anyone have
>a list of the more common of these, and references for extraction?

Here's my paper on psychedelic tryptamines, where I've tried to list all
the known plant sources. If you know something that isn't there please
let me know. Maybe our friend Jeremy could post the excellent extraction
instructions he wrote? You can also find descriptions of extractions from
the articles I've referred to below.

TRYPTAMINE CARRIERS
===================
by Petrus.Pennanen@helsinki.fi             Last update Nov 13 1992

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      ?       ?
-----------------------------------------------------------------------------
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.

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 the beta-carbolines harmine and harmaline, are effective for much
shorter time, maybe up to 24 hours. Reversible MAOIs are not 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 
*data insufficient*, possible consequences are very 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). 

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: Agaricaceae
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/psilocybin. Florida Mycology Research Center
(PO Box 8104 Pensacola Florida 32505) sells spores ($10) and cultures ($112).

Genus:  Psilocybe

These are the psilocin and psilocybin carrying mushrooms, which have
their own section in the Natural Highs FAQ.

Family: Aizoaceae
Genus:  Delosperma

Contains DMT and N-methyltryptamine (see Smith 1977 for refs).

Family: Apocynaceae
Genus:  Prestonia
Species: amazonica?

Contains DMT (Smith 1977).
 
Family: Gramineae
Genus:  Arundo
Species: donax

Leaves, flowers and rhizomes contain DMT, Bufotenine and related compounds
(Ghosal et al. 1972).

Genus: Phalaris
Species: arundinacea
         tuberosa

Leaves of P. arundinacea and leaves and seedlings of P. tuberosa 
contain DMT, 5-MeO-DMT and related compounds (Smith 1977). P.
arundinacea plants are available from ..Of the jungle for $15.

Family: Leguminosae
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) mention other 
species.

Seeds of several acacia species are available from ..Of the jungle.

Genus:  Anadenanthera (Piptadenia)
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:  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:  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:  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).

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: Petalostylis
species: labicheoides

Leaves and stem contain 0.4-0.5% tryptamine, DMT and other alkaloids 
(Johns et al. 1966).

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: 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.
Daly, J.W. & Witkop, B. 1971. Chemistry and pharmacology of frog venoms.
  In: Venomous animals and their venoms. Vol II. New York: Academic Press.
Fitzgerald, J.S. & Sioumis, A.A. 1965. Alkaloids of Australian
  Leguminosae V. Aust. J Chem. 18, 433.
Ghosal, S., Chaudhuri, R.K., Dutta, S.K., Bhattacharya, S.K. 1972. Occurrence 
  of curaromimetic indoles in the flowers of Arundo donax. Planta Med. 21, 22.
Johns, S.R., Lamberton, J.A., Sioumis, A.A. 1966. Alkaloids of the 
  Australian Leguminosae VI. Aust. J Chem. 19, 893.
Kantor, R.E., Dudlettes, S.D. & Shulgin, A.T. 1980. 5-Methoxy-alfa-methyl-
  tryptamine (alfa,O-dimethylserotonin), a hallucinogenic homolog of 
  serotonin. Biological Psychiatry Vol 15:349-352.
Luna, L.E. 1984. The Healing Practices of a Peruvian Shaman. J of
  Ethnopharmacology 11, 123-133. 
McKenna, D.J., Towers, G.H.N., & Abbott, F. (1984). Monoamine oxidase
  inhibitors in South American hallucinogenic plants: Tryptamines and
  Beta-carboline constituents of ayahuasca. J of Ethnopharmacology, 10, 195-223.
Mckenna, Dennis J. & Towers, G.H.N. 1984. Biochemistry and Pharmacology of
  Tryptamines and beta-Carbolines: A Minireview. J Psychoactive Drugs 16(4).
Meckes-Lozoya, M., Lozoya, X., Marles, R.J., Soucy-Breau, C., Sen, A.,
  Arnason, J.T. 1990. N,N-dimethyltryptamine alkaloid in Mimosa tenuiflora
  bark (tepescohuite). Arch. Invest. Med. Mex. 21(2) 175-7.
Most, Albert. Eros and the Pineal: the layman's guide to cerebral 
  solitaire, 1986, Venom Press Box 2863 Denton TX 76202
  (also publishes "Bufo alvarius: The Psychedelic Toad of the Sonoran Desert")
Naranjo, C. 1969. Psychotropic Properties of the Harmala Alkaloids. In: Efron
  (Ed.) The Ethnopharmacologic Search for Psychoactive Drugs.
Pachter, I.J, Zacharias, D.E & Ribeir, O. 1959. Indole Alkaloids of Acer
  saccharinum (the Silever Maple), Dictyoloma incanescens, Piptadenia 
  colubrina, and Mimosa hostilis. J Org Chem 24 1285-7.
Rovelli, B. & Vaughan, G.N. 1967. Alkaloids of Acacia I. Aust. J Chem.
  20, 1299.
Schultes, R.E. 1976. Indole Alkaloids in Plant Hallucinogens. J of
  Psychedelic Drugs Vol 8 No 1 7-25.
Schultes, R.E. 1977. The Botanical and Chemical Distribution of Hallucinogens.
  J of Psychedelic Drugs Vol 9 No 3 247-263.
Schultes, R.E. & Hofmann, A. 1980. The Botany and Chemistry of Hallucinogens. 
  Springfield, Ill: Thomas. pp. 142 & 155.
Shulgin, A.T. 1982. Chemistry of Psychotomimetics. In: Hoffmeister, F. &
  Stille, G. (Eds.) Handbook of Experimental Pharmacology, Vol 55: 
  Alcohol and Psychotomimetics, Psychotropic Effects of Central-Acting 
  Drugs. New York: Springer-Verlag.
Shulgin, A.T. 1976. Psychotomimetic agents. In: Gordon, M. (Ed.)
  Psychopharmacological Agents, Vol IV. New York: Academic Press.
Smith, T.A. 1977. Review: Tryptamine and Related Compounds in Plants.
  Phytochemistry Vol 16 171-175.
Strassman, R.J. 1990. The Pineal Gland: Current Evidence For Its Role In
  Consciousness. In: Lyttle, T. (Ed.) Psychedelic Monographs and Essays
  Vol 5.
Thompson, A.C., Nicollier, G.F. & Pope, D.F 1987. Indolealkylamines of 
  Desmanthus illinoensis and Their Growth Inhibition Activity. J Agric.
  Food Chem. 35 361-365.

Have fun!

Petrus