Life Science Encyclopedia

Psilocin (4-HO-DMT) sometimes also (mis)spelled psilocine, psilocyn, or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances.^[1]

History

The Swiss chemist Albert Hofmann and the laboratory assistant Hans Tscherter from Sandoz isolated psilocin and its phosphate ester psilocybin from Psilocybe mushrooms in 1959 guided by self-administration.

Chemistry

Psilocin can be obtained by dephosphorylation of natural psilocybin under strongly acidic or under alkaline conditions (hydrolysis). Another synthetic route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole.

Psilocin is relatively unstable in solution due to its phenolic OH group. In the presence of oxygen it readily forms bluish and dark black degradation products. Similar products are also formed under acidic conditions in the presence of oxygen and Fe³⁺ ions (Keller's reagent, FeCl₃ / MeOH / HCl).

Pharmacology

Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or psychedelic mushrooms.

Psilocybin is rapidly dephosphorylated in the body to psilocin which acts as a 5HT_2A, 5HT_2C and 5HT_1A agonist. It's effects are thought to come from it's ability to mimic serotonin (5-HT) and thereby activate serotonin receptors in the brain.

Psilocin has no significant effect on dopamine receptors (unlike LSD) and only affects the norephenephrine system at very high dosages.^[2]

Psilocin half-life ranges from 2 to 3 hours.^[3]

See psilocybin for more details.

See also

• Psychedelic mushrooms
• Psilocybin
• Tryptamine
• Indole
• Psychedelic drug
• Psychoactive drug

References

1. ^ "Green list"
2. ^ Psilocybin Investigator’s Brochure
3. ^ Psilocybin Investigator’s Brochure