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O-acetylpsilocin
Sign in to saveAlso known as psilacetin, acetylpsilocin, 4-AcO-DMT
'4-Acetoxy-N,N-dimethyltryptamine (4-AcO-DMT or 4-acetoxy-DMT), also known as O-acetylpsilocin or psilacetin', is a psychedelic drug of the tryptamine family related to psilocybin and psilocin. It is a synthetic derivative of psilocin (4-HO-DMT) in which the hydroxyl group has been acetylated, and is the analogue of psilocybin (4-PO-DMT) in which the phosphate ester has been replaced with an acetate ester. The drug is a prodrug of psilocin and is used orally similarly to psilocybin.
Chemical data
- Formula
- C14H18N2O2
- Molecular weight
- 246.3 g/mol
- IUPAC name
- [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] acetate
- SMILES
- CC(=O)OC1=CC=CC2=C1C(=CN2)CCN(C)C
- InChIKey
- RTLRUOSYLFOFHV-UHFFFAOYSA-N
- XLogP
- 2.1
- Polar surface area
- 45.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- tryptamines
- Mass
- 246.137
Show 3 more facts
- chemical formula
- C₁₄H₁₈N₂O₂
- canonical SMILES
- CC(=O)OC1=CC=CC2=C1C(=CN2)CCN(C)C
- Commons category
- Acetylpsilocin
Sources (2)
via Wikidata · CC0
~12 min read
Encyclopedic overview
27 sectionsContents
- Use and effects
- Contraindications
- Side effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Synthesis
- Stability
- Analogues
- History
- Society and culture
- Legal status
- International
- Australia
- Canada
- Czech Republic
- Germany
- Israel
- Italy
- Sweden
- United Kingdom
- United States
- See also
- References
- External links
'4-Acetoxy-N,N-dimethyltryptamine (4-AcO-DMT or 4-acetoxy-DMT), also known as O-acetylpsilocin or psilacetin', is a psychedelic drug of the tryptamine family related to psilocybin and psilocin. It is a synthetic derivative of psilocin (4-HO-DMT) in which the hydroxyl group has been acetylated, and is the analogue of psilocybin (4-PO-DMT) in which the phosphate ester has been replaced with an acetate ester. The drug is a prodrug of psilocin and is used orally similarly to psilocybin.
As a prodrug of psilocin, 4-AcO-DMT acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor. The hallucinogenic effects of psilocin are thought to be mediated by activation of this receptor, although other receptors also contribute to its effects. 4-AcO-DMT's effects are reported to be similar to those of psilocybin and psilocybin mushrooms. However, it has been said to have reduced side effects such as nausea and body load that can be caused by ingestion of whole psilocybin mushrooms. It is also said to have a faster onset and shorter duration than psilocybin. The drug is not expected to differ from psilocybin or psilocin in terms of safety. 4-AcO-DMT is modestly less potent by weight than psilocybin in animals when they are given at equimolar doses.
Excerpted from Wikipedia’s “O-acetylpsilocin” article, available under the CC BY-SA 4.0 licence.