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 synthetic routes to these chemicals.[5]
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 procedure. 4-hydroxyindole is acylated with oxalyl chloride. The compound is further reacted with an amine, yielding indole-3-yl-glyoxalyamide. Finally, the product amide is reduced using lithium aluminum hydride yielding psilocin.[6]
Psilocin is relatively unstable in solution due to its phenolichydroxy (-OH) group. In the presence of oxygen, it readily forms bluish and dark black degradation products.[7] Similar products are also formed under acidic conditions in the presence of oxygen and Fe3+ions (Keller's reagent).
Structural analogs
Sulfur analogs are known with a benzothienyl replacement[8] as well as 4-SH-DMT.[9]1-Methylpsilocin is a functionally 5-HT2C receptor preferring agonist.[10] 4-Fluoro-N,N-dimethyltryptamine is known.[10]O-Acetylpsilocin (4-AcO-DMT) 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 (4-hydroxy-N-methyl-N-isopropyltryptamine) and 4-HO-MET (4-hydroxy-N-methyl-N-ethyltryptamine), respectively. 4-Acetoxy-MET (4-Acetoxy-N-methyl-N-ethyltryptamine), also known as 4-AcO-MET, is the acetate ester of 4-HO-MET, and a homologue of 4-AcO-DMT.
Dried psilocybin mushrooms. (Notice the characteristic blue bruising by the stems of the mushrooms.)
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 (common at medium to high doses), synesthesia (e.g. hearing colours and seeing sounds), increased body temperature, headache, sweating and chills, and nausea. Psilocin acts as a 5-HT2A, 5-HT2C, and 5-HT1A receptor agonist or partial agonist. Such receptors are claimed to significantly regulate visuals, decision making, mood, decreased blood pressure, and heart rate.[11]
The United Nations Convention on Psychotropic Substances (adopted in 1971) requires its members to prohibit psilocybin, and parties to the treaty are required to restrict the use of the drug to medical and scientific research under strictly controlled conditions.
Australia
Psilocin is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[13] 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.[13]
Russia
Psilocin and psilocybin are banned in Russia as narcotic drugs with a criminal penalty for possession of at least 50 mg.[14]
^Hofmann A, Heim R, Brack A, Kobel H, Frey A, Ott H, Petrzilka T, Troxler F (1959). "Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen" [Psilocybin and psilocin, two psychotropic substances in Mexican magic mushrooms]. Helvetica Chimica Acta (in German). 42 (5): 1557–72. doi:10.1002/hlca.19590420518.
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