O-Acetylpsilocin and several other esters of psilocin were patented on January 16, 1963 by Sandoz Ltd via Albert Hofmann & Franz Troxler. Despite this, psilacetin remains a psychedelic compound with a limited history of use. It is theorized to be a prodrug of psilocin, as is psilocybin, which occurs naturally in many species of hallucinogenic mushrooms. This is because the aromatic acetyl moiety on the 4th position of the indole ring system is subject to deacetylation in acidic conditions such as those found in the stomach. Psilacetin is O-acetylated psilocin, whereas psilocybin is O-phosphorylated.
Chemistry
O-Acetylpsilocin can be obtained by acetylation of psilocin under alkaline or strongly acidic conditions. It is, therefore, a semi-synthetic compound. It is believed to be a prodrug of psilocin; however, speculation exists that psilacetin itself also may be psychoactive. O-Acetylpsilocin is more resistant than psilocin to oxidation under basic conditions due to its acetoxy group. While O-acetylpsilocin is not well researched, it is not as difficult as psilocybin to synthesize. Due to their similar proposed mechanisms of action, this factor may provide further support for the proposition that O-acetylpsilocin might serve as an appropriate substitute for psilocybin in research of the application of psychedelic compounds in medicine.
Pharmacology
In the body O-acetylpsilocin is deacetylated to psilocin by deacetylases/acetyltransferases during first pass metabolism and during subsequent passes through the liver. Claims of subjective differences in effects between the acetylated and non-acetylated forms of psilocin vary: some users report that O-acetylpsilocin lasts slightly longer, whilst others report that it lasts for a considerably shorter time. Many users report less body load and nausea compared with psilocin. Some users find that the visual effects produced by O-acetylpsilocin more closely resemble those produced by DMT than those produced by psilocin or psilocybin. These differences could be possible if psilacetin is psychoactive in itself and not merely as a prodrug. Despite this, there have been no controlled clinical studies to distinguish among the phenomenological effects of psilacetin, psilocin, and psilocybin.
Legality
Australia
O-Acetylpsilocin can be considered an analog of psilocin making it 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.
O-Acetylpsilocin is illegal in Italy as it is an ester of a prohibited substance.
Sweden
added 4-AcO-DMT to :sv:Narkotikastrafflagen|Narcotic Drugs Punishments Act under swedish schedule I as of January 25, 2017, published by Medical Products Agency in regulation HSLF-FS 2017:1 listed as 4-acetoxi-N,N-dimetyltryptamin.
