O-Acetylpsilocin

O-Acetylpsilocin
Clinical data
Other namesPsilacetin; 4-Acetoxy-N,N-dimethyltryptamine; 4-Acetoxy-DMT; 4-AcO-DMT; Synthetic shrooms; 3-(2'-Dimethylaminoethyl)-4-acetoxyindole[1]
Routes of
administration		Oral, intravenous, intranasal, rectal
ATC code
  • None
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class F2 (Prohibited psychotropics)
  • CA: Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: Unscheduled
Identifiers
  • 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl acetate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H18N2O2
Molar mass246.310 g·mol−1
3D model (JSmol)
Melting point172 to 173 °C (342 to 343 °F)
  • CC(=O)Oc2cccc1[nH]cc(CCN(C)C)c12
  • InChI=1S/C14H18N2O2/c1-10(17)18-13-6-4-5-12-14(13)11(9-15-12)7-8-16(2)3/h4-6,9,15H,7-8H2,1-3H3 checkY
  • Key:RTLRUOSYLFOFHV-UHFFFAOYSA-N checkY
  (verify)

Psilacetin, also known as O-acetylpsilocin or as 4-acetoxy-N,N-dimethyltryptamine (4-acetoxy-DMT or 4-AcO-DMT), is a semi-synthetic serotonergic psychedelic drug that 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.[2][3] However, some users report that O-acetylpsilocin's subjective effects differ from those of psilocybin and psilocin.[4][5] Additionally, some users prefer 4-AcO-DMT to natural psilocybin mushrooms due to feeling fewer adverse side effects such as nausea and heavy body load, which are more frequently reported in experiences involving natural mushrooms.[6] 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 2024, it was confirmed that psilacetin is indeed a prodrug of psilocin.[7]

  1. ^ US patent 3075992, Hofmann A, Troxler F, "Esters of indoles", assigned to Sandoz Ltd. 
  2. ^ Nichols D, Fescas S (1999). "Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin" (PDF). Synthesis. 1999 (6): 935–938. CiteSeerX 10.1.1.690.8071. doi:10.1055/s-1999-3490. S2CID 32044725. Archived (PDF) from the original on 17 February 2012. Retrieved 17 January 2012.
  3. ^ Bauer BE (2019-09-18). "The State of the Art of Psilacetin (4-AcO-DMT)". Psychedelic Science Review. Retrieved 2021-02-13.
  4. ^ "4-AcO-DMT (also 4-acetoxy-N,N-dimethyltryptamine) : Erowid Exp: Main Index". www.erowid.org. Archived from the original on 2010-07-28.
  5. ^ Janikian M (2020-05-26). "The Complete Guide: 4-AcO-DMT a.k.a. Synthetic Shrooms". DoubleBlind Mag.
  6. ^ Palamar JJ, Acosta P (January 2020). "A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines". Human Psychopharmacology. 35 (1): e2719. doi:10.1002/hup.2719. PMC 6995261. PMID 31909513.
  7. ^ Jones NT, Wagner L, Hahn MC, Scarlett CO, Wenthur CJ (2023). "In vivo validation of psilacetin as a prodrug yielding modestly lower peripheral psilocin exposure than psilocybin". Front Psychiatry. 14: 1303365. doi:10.3389/fpsyt.2023.1303365. PMC 10804612. PMID 38264637.