Entheogenic Tryptamines of Shamanic

Origins :

Ayahuasca Psilocybin

Presented By:
Stacey King,
Derek Lee, and Steven Phillips
01/19/01
 History
Definition:
An Amazonian brew, also called yage, containing powerful
hallucinogenic alkaloids used for spiritual purposes. In native
Quechuan language “ayahuasca” means “vine of the dead.”

Folk Use:
--Pre-Columbian rock drawings
--Early explorer- Richard Spruce
--Medicine of the Amazonian shamans
 Preparation
Gathering:
Prayer and fasting

Ingredients/Botany:
Banisteriopsis caapi - Vine of the soul
Psychotria viridis - Chacruna
Diplopterys cabrerana
Peganum harmala
others

Preparation:
Pulverize B. Caapi and boil with P. viridis and other admixture plants for 12- 15 hours

Synthetic Versions:
Pharmahuasca
Banisteriopsis caapi and Psychotria viridis

Banisteriopsis caapi
 Effects

The Purge:
Natural vs. synthetic

Hallucination:
“Elves”, mandala-like designs, life visions

Physiological:
Statically higher upregulation of serotonin receptors (Callaway et. al., 1994)
EEG shows a higher activity in the visual band (Don et. al., 1998)
 Monoamine Oxidase Inhibitors
Monoamine oxidase:
An enzyme that oxidatively deaminates other biogenic amines such as serotonin,
tryptamine, and tyramine, rendering them inactive.

Inhibitors: Beta- Carbolines

• Ayahuasca = 158 mg/dose Pharmahuasca = 1.5 mg/kg
• Harmaline and harmine (dihydroharmine and tetrahydroharmine) found in B.
caapi and P. harmala are reversible inhibitors of MAO-A found in the CNS
and MAO-B found in the gastrointestinal tract
• Evidence: clinical trial by McKenna, Towers, and Abbott (1984)
• Effects:Beta-carbolines from P. harmala alone elicit a sedative, valium-like
psychoactivity, in constrast to B. caapi which is more of a mood up-lifter.
Minor hallucinogenic properties in high doses
– harmala as an abortificant
Beta-Carboline Structures

Harmaline

Tetrahydroharmine

Harmine
Warning: Dangerous Interactions
Hypertensive crisis: Foods to Avoid!!!!!
Taking food with Tyramine
Cheese
increases levels of Epinephrine
Alcoholic beverages
resulting in high blood pressure,
treated with nifedipine or
Ginseng
clonidine Aged Meat
(sausage, bologna, salami)
Toxic Serotomimetic Reaction: Soy sauce
a.k.a. serotonin syndrome
Chocolate and Coffee (lg. amts.)
Overstimulation of serotonin
causing rigidity, shivering, and
and confusion, treated with
5-HT2 blockers
Hallucinogenic Compounds
 DMT
(dimethyltryptamine)

• Taxa containing DMT: Psychotria viridis, Diplopterys cabrerana,

Mimosa hostilis, Homo sapiens, several others
• Peripheral effects include: increased blood pressure, heart rate,
core body temperature, endorphins, prolactin, and pupil dilation
• Hallucinogenic effects of ayahuasca due to DMT
• Routes of administration: in order of potency (strong effects)
IV injection---- .4 mg/kg
inhalation------ .7 mg/kg
IM injection---- 1 mg/kg
oral-------------- inactive unless in presence of MAO inhibitor
.38 mg/kg threshold to .8 mg/kg for strong

• Duration (results will vary)

DMT + harmine: 45-60 min incubation
build within 30 min of incubation
plateau 45-60 min
1 hour of diminishing effects
inhalation: instant peak effects lasting 5-10 min
residual effects 30-60 min
What? Humans the new source of
DMT!?
• Small amounts of DMT are found in human spinal fluid,
blood, and urine.
• Methyl transferases catalyse synthesis of tryptamines are
found in the human lung, brain, cerbrospinal fluid, liver
and heart.
• Transmethylation Hypothesis:
– Schizophrenics produce a higher concentration of
methylated indolealkyalamines (eg. DMT)
 Proposed Mechanism of Action
• DMT acts on serotonin receptors (5-HT2A, 5-HT2C,
5-HT5B, 5-HT7) which are G- protein coupled and
contain a 7 transmembrane domain structure
• The function of these receptors include:
stimulating phospolipase C, increasing
phosphoinositide hydrolysis, and increasing
cAMP
Serotonin and Psilocin
Proposed Biosynthesis of DMT
CO2H
- CO2
NH2 HH2
N decarboxylation by pyridoxal phosphate N
H H
Tryptophan
SAM

SAM

CH3
N
CH3
N
H

DMT
 Teonanacatl:
The Mushroom Flesh of the Gods
(Psilocybin and Psilocin)

Psilocybe cubensis
 History

– Archaeological evidence from 1000 B.C.E.

– Spanish conquistadors
– Gordon Wasson
– Alkaloid determination
– Timothy Leary, inmates, CIA, and hippies
 Psychopharmacology

– Threshold dose = 5 mg
– Typical dose = 10-20 mg
– 30 times more potent than mescaline
– .01 times as potent as LSD
– Subjective comparison to LSD vs. Leary’s hypothesis:
less abstract, not a stimulant
– Duration: 4-6 hours
– Oral Activity
– Potentiated by MAOI but not required
Have you licked a toad today?

Bufo alvarius
 Bufotenine: Does it really work?
•Structurally similar to known psychoactive tryptamines
•Binds at same serotonin receptors as known psychoactive
tryptamines
•Other “goodies” in the toad
•Can it reach the brain?
Partition Coefficients
Drug Part. Coef.
5-MeO-DMT 3.30
Psilocin 3.30
Bufotenine 0.06
•The epinephrine factor (Chen & Kovarikova, 1967.)
•B. alvarius vs. B. marinus
 References
Baskys, A Remington, G (1996): “Brain Mechanisms and Psychotropic Drugs”.
Callaway, J et. al. (1994): “Platelet Serotonin Uptake Sites Increased in Drinkers
of Ayahuasca”. Psychopharmacology 116: (3) 385-387
Chin and Kovarikova (1967): “Pharmacology and Toxicology of Toad Venom”.
Journal of Pharmaceutical Science 56:1535-41
Don N et. al. (1998): “Effects of Ayahuasca on the Human EEG”.
Phytomedicine 5: (2) 87-96
McBride, M (2000): “Bufotenine: Toward an Understanding of Possible
Psychoactive Mechanisms”. Journal of Psychoactive Drugs 32: (3) 321-331
Ott, J (1999): “Pharmahuasca: Human Pharmacology of Oral DMT Plus
Harmine”. Journal of Psychoactive Drugs 31: (2) 171-177
Perrine, D (1996): “The Chemistry of Mind-Altering Drugs”.