Psilocin

Wikipedia, the free encyclopedia - Cite This Source

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.

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).

Sulfur analogs are known with benzothienyl/indolyl and 4-OH/-SH replacement.

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. Psilocin is structurally similar to serotonin (5-HT), and its effects are thought to come from its ability to mimic serotonin 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.

Psilocin half-life ranges from 2 to 3 hours.

See psilocybin for more details.

Behavioral and Non-behavioral Effects

The general characteristics of the hallucinations induced by psilocin are virtually identical to those induced by mescaline, except the duration of its effect are comparatively shorter, lasting approximately four hours.

It elicits a pattern similar to a sympathetic arousal state. Specific behaviors observed after ingestion can include increased heart rate, dilated pupils, restlessness or arousal, increased body temperature, headache, sweating and chills, and nausea.

There is virtually no direct lethality associated with psilocin. There is virtually no withdrawal syndrome when chronic use of this drug is ceased. There is cross tolerance among psilocin, mescaline, and LSD.

See also

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

References

External links

• The Ones That Stain Blue Studies in ethnomycology including the contributions of Maria Sabina, Dr. Albert Hofmann and Dr. Gaston Guzman.
• The Shroomery Detailed information about Psilocybin mushrooms including identification, cultivation and spores, psychedelic images, trip reports, a dosage calculator and an active community.
• 4-HO-DMT entry in TiHKAL

Wikipedia, the free encyclopedia © 2001-2006 Wikipedia contributors (Disclaimer)
This article is licensed under the GNU Free Documentation License.
Last updated on Tuesday March 11, 2008 at 17:00:16 PDT (GMT -0700)
View this article at Wikipedia.org - Edit this article at Wikipedia.org - Donate to the Wikimedia Foundation