1. Hallucinogens - III: Magic Mushrooms and Other Hallucinogenic Fungi
Psychoactive Plants
Hallucinogens - III: Magic Mushrooms and Other Hallucinogenic Fungi

2. THE FUNGI Kingdom Protista Div Myxomycota Kingdom Eumycota
Div Oomycota
Kingdom Eumycota
Div Chytridiomycota
Div Zygomycota
Div Ascomycota
Div Basidiomycota
Asexual Fungi

3. 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

4. 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

5. Claviceps purpurea
Ergot of rye

6. 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

7. Ergot alkaloids
Vindoline
Vinblastine (Catharanthus)

8. 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
– Hofmann – LSD-25

9. Lysergic acid structure

10. 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

11. 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

12. 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

13. Ibotenic Acid and Muscimol
Amanita muscaria (fly agaric)
Amanita pantherina (panther cap)
Amanita cothurnata
Amanita gemmata
Amanita smithiana
Amanita strobiliformis
Tricholoma muscarius
Panaeolus campanulatus????

14. 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

15. 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 hours after ingestion of the mushrooms

16. Ibotenic Acid and Muscimol
Muscimol lacks the carboxyl group

17. 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

18. 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

19. Psilocybin and Psilocin
Psilocybe
Psilocybe cubensis
Conocybe
Gymnopilus
Panaeolus

20. 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

21. 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

22. 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

23. Psilocin
Serotonin

24. Symptoms Primary symptom: hallucinations Other possible symptoms:
Fear, agitation, confusion, psychoses
Vomiting
Prostration
Temporary paralysis
Poisoning rarely fatal in adults