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O-Acetylpsilocin (also known as psilacetin, 4-acetoxy-DMT, or 4-AcO-DMT) is a synthetically produced psychoactive drug and has been suggested by David Nichols to be a potentially useful alternative to psilocybin for pharmacological studies, as they are both believed to be prodrugs of psilocin.

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However, some users report that O-acetylpsilocin’s subjective effects differ from that of psilocybin and psilocin. It is the acetylated form of the psilocybin mushroom alkaloid psilocin and is a lower homolog of 4-AcO-MET, 4-AcO-DET, 4-AcO-MiPT and 4-AcO-DiPT.

In the body O-acetylpsilocin is deacetylated to psilocin by deacetylases/acetyltransferases during first pass metabolism[citation needed] and during subsequent passes through the liver (evident as psilacetin is also active via parenteral routes of ingestion). Claims of subjective differences in effect between the acetylated and not acetylated forms of psilocin; some users report that O-acetylpsilocin lasts slightly longer; others report that it lasts for a considerably shorter time. Many users report less body load and nausea compared to psilocin.

Some users find that the visual distortions produced by O-acetylpsilocin more closely resemble those produced by DMT than those produced by psilocin. These differences could be possible if psilacetin is active itself and not merely as a prodrug. Despite this, there have been no controlled clinical studies to distinguish the effects between psilacetin, psilocin, and psilocybin.

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44-ACO-DMT and several other esters of psilocin were originally patented on January 16, 1963 by Sandoz Ltd. via Albert Hofmann & Franz Troxler. Despite this fact, 4-AcO-DMT remains a psychedelic with a limited history of use prior to its release as a grey area compound on the online research chemical market. 4-ACO-DMT ‘s psychedelic effects are believed to come from its efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

In the body, 4-AcO-DMT / psilacetin is thought to be deacetylated into psilocin during first pass metabolism and subsequent passes through the liver (evident as psilacetin is also active when injected). This has not been formally proven, however, and is based on reports that most users cannot tell the difference between these two compounds when ingested to the point that they are often considered as indistinguishable from each other in terms of their subjective effects. Many users report less body load and nausea compared to psilocin.

Some users find that the visual distortions produced by 4-AcO-DMT more closely resemble those produced by DMT than those produced by psilocin. These differences could be possible if 4-AcO-DMT is active itself and not merely as a prodrug.