Psilocin and its phosphorylated cousin, psilocybin, were first isolated and named in 1958 by Swiss chemist Albert Hofmann. Hofmann obtained the chemicals from laboratory-grown specimens of the entheogenicmushroomPsilocybe mexicana. Hofmann also succeeded in finding the synthetic routes to these chemicals. Psilocin can be obtained by dephosphorylation of natural psilocybin under strongly acidic or under alkaline conditions. Another synthetic route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole. Psilocin is relatively unstable in solution due to its phenolichydroxy 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.
Structural analogs
analogs are known with a benzothienyl replacement as well as 4-SH-DMT. 1-Methylpsilocin is a functionally 5-HT2C receptor preferring agonist. 4-Fluoro-N,N-dimethyltryptamine is known. O-Acetylpsilocin is an acetylated analog of psilocin. Additionally, replacement of a methyl group at the dimethylated nitrogen with an isopropyl or ethyl group yields 4-HO-MIPT and 4-HO-MET, respectively.
Pharmacology
Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or some species of psychedelic mushrooms. Psilocybin is rapidly dephosphorylated in the body to psilocin which acts as a 5-HT2A, 5-HT2C and 5-HT1A agonist or partial agonist. Psilocin exhibits functional selectivity in that it activates phospholipase A2 instead of activating phospholipase C as the endogenous ligandserotonin does. Psilocin is structurally similar to serotonin, differing only by the hydroxyl group being on the 4-position rather than the 5 and the dimethyl groups on the nitrogen. Its effects are thought to come from its partial agonist activity at 5-HT2Aserotonin receptors in the prefrontal cortex. Psilocin has no significant effect on dopamine receptors and only affects the noradrenergic system at very high dosages. Psilocin's half-life ranges from 1 to 3 hours.
Behavioral and non-behavioral effects
Its physiological effects are similar to a sympathetic arousal state. Specific effects observed after ingestion can include but are not limited to tachycardia, dilated pupils, restlessness or arousal, euphoria, open and closed eye visuals, synesthesia , increased body temperature, headache, sweating and chills, and nausea. Psilocin acts as a 5-HT2A, 5-HT2C and 5-HT1A agonist or partial agonist. Receptors are claimed to significantly regulate visuals, decision making, mood, decreased blood pressure and heart rate. 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, LSD, and other 5-HT2A, 5-HT2C, and 5-HT1A agonists due to down-regulation of these receptors.
Psilocin is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard. A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.
Russia
Psilocin and psilocybin are banned in Russia as narcotic drugs with a criminal penalty for possession of at least 50 mg.
