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entheogenic tryptamines of shamanic origins ayahuasca psilocybin

Entheogenic Tryptamines of Shamanic Origins :Ayahuasca Psilocybin

Presented By:

Stacey King,

Derek Lee, and Steven Phillips




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



Prayer and fasting


Banisteriopsis caapi - Vine of the soul

Psychotria viridis - Chacruna

Diplopterys cabrerana

Peganum harmala



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

Synthetic Versions:



The Purge:

Natural vs. synthetic


“Elves”, mandala-like designs, life visions


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 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
Beta-Carboline Structures





Hypertensive crisis:

Taking food with Tyramine

increases levels of Epinephrine

resulting in high blood pressure,

treated with nifedipine or clonidine

Toxic Serotomimetic Reaction:

a.k.a. serotonin syndrome

Overstimulation of serotonin

causing rigidity, shivering, and

and confusion, treated with

5-HT2 blockers

Foods to Avoid!!!!!


Alcoholic beverages


Aged Meat

(sausage, bologna, salami)

Soy sauce

Chocolate and Coffee (lg. amts.)

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
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
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


  • Archaeological evidence from 1000 B.C.E.
  • Spanish conquistadors
  • Gordon Wasson
  • Alkaloid determination
  • Timothy Leary, inmates, CIA, and hippies


  • 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
bufotenine does it really work
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
  • DrugPart. Coef.
  • 5-MeO-DMT 3.30
  • Psilocin 3.30
  • Bufotenine 0.06
  • The epinephrine factor (Chen & Kovarikova, 1967.)
  • B. alvarius vs. B. marinus

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”.