Hallucinogens - III: Magic Mushrooms and Other Hallucinogenic Fungi
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Transcript of Hallucinogens - III: Magic Mushrooms and Other Hallucinogenic Fungi
Psychoactive PlantsHallucinogens - III: Magic Mushrooms and Other Hallucinogenic Fungi
THE FUNGIKingdom Protista
Div Myxomycota
Div OomycotaKingdom Eumycota
Div Chytridiomycota
Div Zygomycota
Div Ascomycota
Div BasidiomycotaAsexual Fungi
Kingdom Fungi Division Ascomycota (ascomycetes) - yeasts,
mycelial fungi, morels, cup fungi, truffles Division Basidiomycota (basidiomycetes) -
mushrooms, bracket fungi, puffballs, Asexual Fungi (imperfect fungi) - artificial
group of mycelial fungi with no sexual stage - molds
Hallucinogenic Fungi Hallucinogenic compounds found in many
fungi Ascomycota - Claviceps purpurea - ergot
compounds - Lysergic acid alkaloids - LSD Basidiomycota - several mushrooms
Amanita muscaria, A. pantherina, and others Psilocybe and related fungi
Claviceps purpurea
Ergot of rye
Ergotism Ergot contains a number of toxic alkaloids, if
harvested with the grain and milled into the flower - it causes a disease called ergotism
During Middle Ages called “Dancing Mania” and “St. Anthony’s Fire”
Many alkaloids found in the ergot Some constrict blood vessels Some act on CNS
Ergotism rare today but historically important
Ergot alkaloids
Vindoline
Vinblastine (Catharanthus)
The Road to LSD Late 19th and early 20th centuries chemists began to
isolate active principles of ergot In 1918 Stoll, Swiss chemist, isolated an alkaloid
which he named ergotamine Early 1930's Jacobs and Craig basic structure of all
ergot alkaloids - lysergic acid 1935 – Albert Hofmann – ergobasine 1938-1943 – Hofmann – LSD-25
Lysergic acid structure
A new hallucinogen Hofmann decided to
experiment with LSD-25 on himself
On April 19, 1943, he took 0.25 mg of LSD-25 - birth of a hallucinogen
Effects of LSD
Mode of Action Effects mid-brain activity by interfering with
action of serotonin and serotonin receptors In small amounts mimics serotonin but in
larger amounts it is antagonistic to serotonin Hallucinations due to disruptions in the
normal pathways of sensory stimulation
Hallucinogenic Mushrooms Two different toxin groups exhibit
hallucinogenic properties Ibotenic acid and Muscimol in the family
Amanitaceae (and possibly others) Psilocybin (psilocin) in several mushroom families
Strophariaceae Bolbitiaceae Cortinariaceae Coprinaceae
Ibotenic Acid and MuscimolAmanita muscaria (fly agaric)Amanita pantherina (panther cap)Amanita cothurnata Amanita gemmata Amanita smithiana Amanita strobiliformis Tricholoma muscarius Panaeolus campanulatus????
Amanita muscaria Long history of use as an intoxicant Used by native peoples in many parts of the world Possibly used in India for 4000 years - Soma hymns
of Rig Veda have been interpreted as description of A. muscaria
Used for centuries by tribes in Siberia Excreted unaltered - so urine collected and drunk for a
second dose among the poor
Ibotenic Acid and Muscimol Both substances produce the same effects, but
muscimol is approximately 5 to 10 times more potent than ibotenic acid
Ibotenic acid converted to muscimol on drying and cmpds last 5-10 yrs in dried mushrooms
Ibotenic acid may be converted into muscimol in the body
Symptoms of poisoning generally occur within 1 - 2 hours after ingestion of the mushrooms
Ibotenic Acid and Muscimol
Muscimol lacks the carboxyl group
Muscimol Muscimol's primary action is at GABA receptor sites
as a potent GABA-A agonist GABA - inhibitory neurotransmitter - inhibitor of
presynaptic transmission in the CNS and also in the retina
Muscimol has been shown to be active in several parts of the brain including the cerebral cortex, hippocampus, and cerebellum
Symptoms Manic behavior, delirium, inebriation, spasms Deep sleep full of fantastic images and vivid hallucinations May progress into more serious symptoms including
seizures and possibly coma Many cases of poisoning in this group of mushrooms are
known, but only a few deaths 10 mushrooms a fatal dose - much more serious in kids -
lower doses fatal No antidotes - stomach pumped
Psilocybin and Psilocin Psilocybe
Psilocybe cubensis Conocybe Gymnopilus Panaeolus
Psilocybin and Psilocin Containing Mushrooms
Used for psychoactive effects in religious ceremonies of certain Native American tribes for hundreds of years especially in Mexico and Central America
Aztecs described their sacred mushrooms as Teonanacatl - the flesh of the Gods
Used in religious and healing rites for thousands of years
Suppressed by Spanish but not abandoned Rediscovered in 20th century
Magic Mushrooms Psilocybe cubensis -magic mushrooms of street use Active compounds psilocybin/psilocin Compounds partially similar in structure to LSD -
contain an indole backbone Again act as mimic to serotonin - so effects may be
through serotonin receptors
Psilocybin In the body psilocybin
is hydrolyzed to psilocin - the phosphate group lost
Psilocin is just as potent as psilocybin and is even closer to the structure of serotonin
Serotonin
Psilocin
Symptoms Primary symptom: hallucinations Other possible symptoms:
Fear, agitation, confusion, psychoses Vomiting Prostration Temporary paralysis
Poisoning rarely fatal in adults