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.[6]
Psilocin can be obtained by
dephosphorylation of natural psilocybin under strongly
acidic or under
alkaline conditions (
hydrolysis). A
synthetic route uses the Speeter–Anthony tryptamine synthesis procedure. First, 4-hydroxyindole is
Friedel-Crafts-
acylated with oxalyl chloride in position 3. The compound is further reacted with
dimethylamine, yielding the indole-3-yl-glyoxamide. Finally, this 4-hydroxyindole-3-N,N-dimethylglyoxamide is reduced by lithium aluminum hydride yielding psilocin.[7]
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.[8] Similar products are also formed in the presence of oxygen and
Fe3+ions.
Structural analogs
Sulfur analogs are known with a
benzothienyl replacement[9] as well as 4-
SH-DMT.[10]1-Methylpsilocin is a functionally
5-HT2C receptor preferring agonist.[11] 4-Fluoro-N,N-dimethyltryptamine is known.[11]O-Acetylpsilocin (4-AcO-DMT) is the ester of acetic acid with 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.
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.[12]
There has been no direct lethality associated with psilocin.[12][14] There has been no reported withdrawal syndrome when chronic use of this drug is ceased.[12][15] There is
cross tolerance among psilocin,
mescaline,
LSD,[12][16] and other 5-HT2A, 5-HT2C, and 5-HT1A agonists due to down-regulation of these receptors.
Legal status
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).[17] 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.[17]
Russia
Psilocin and psilocybin are banned in Russia, due to their status as narcotic drugs, with a criminal penalty for possession of more than 50 mg.[18]
^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.