4-AcO-DMT

4-AcO-DMT
Clinical data
Other names4-Acetoxy-N,N-dimethyltryptamine; 4-Acetoxy-DMT; 4-AcO-DMT; O-Acetylpsilocin; Psilacetin; Psiloacetin; Synthetic shrooms
Routes of
administration		Oral, intravenous, intranasal, rectal
Drug classSerotonergic psychedelic; Hallucinogen; Serotonin receptor agonist
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: Federally unscheduled; illegal under the Federal Analogue Act
Identifiers
IUPAC name
  • 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)
SMILES
  • CC(=O)Oc2cccc1[nH]cc(CCN(C)C)c12
InChI
  • 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 Y
  • Key:RTLRUOSYLFOFHV-UHFFFAOYSA-N Y
  (verify)

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.[1][2][3][4] 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.[1][2][3] The drug is a prodrug of psilocin and is orally active similarly to psilocybin.[1][2][5]

As a prodrug of psilocin, 4-AcO-DMT acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[1][6] The hallucinogenic effects of psilocin are thought to be mediated by activation of this receptor, although other receptors also contribute to its effects.[7][8][1] 4-AcO-DMT's effects are reported to be similar to those of psilocybin and psilocybin mushrooms.[2][5][1] 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.[2][5][1] It is also said to have a faster onset and shorter duration than psilocybin.[5] The drug is not expected to differ from psilocybin or psilocin in terms of safety.[1] 4-AcO-DMT is modestly less potent by weight than psilocybin in animals when they are given at equimolar doses.[2]

4-AcO-DMT was first described in a patent by Albert Hofmann in 1963 and its chemical synthesis was improved by David E. Nichols and colleagues in 1999.[2][6][3] It was suggested by Nichols as a more economical and accessible alternative to psilocybin for use in scientific research, as the synthesis of psilocybin is more challenging and as psilocybin is a controlled substance.[2][6][3] 4-AcO-DMT was first detected as a designer drug in Europe in 2009.[6] It became increasingly prevalent as a recreational drug in the 2010s and has been the most commonly used novel tryptamine.[2][5] In the 2020s, 4-AcO-DMT became widely encountered in the form of mushroom edibles in the United States as an alternative to psilocybin.[9][10][11][12] Relatedly, it has sometimes been referred to as "synthetic shrooms".[4] Mushrooms edibles may contain 4-AcO-DMT, Amanita muscaria mushroom constituents, or non-mushroom drugs such as bath salts, and have been linked to poisonings and deaths.[13][4][12][9]

4-AcO-DMT is not scheduled under United States law or any international drug schedules, including the United Nations 1971 Convention on Psychotropic Substances, making it a potentially more accessible alternative to psilocybin for research.[2] It can be imported and possessed for research in the United States if labeled “not for human consumption,” but using it in vivo is illegal and violates the Federal Analogue Act.[1]

  1. ^ a b c d e f g h i Geiger HA, Wurst MG, Daniels RN (October 2018). "DARK Classics in Chemical Neuroscience: Psilocybin" (PDF). ACS Chem Neurosci. 9 (10): 2438–2447. doi:10.1021/acschemneuro.8b00186. PMID 29956917. A chemically modified psilocin precursor, known as psilacetin (20), O-acetylpsilocin, or 4-acetoxy-N,N-dimethyltryptamine, which replaces the phosphoryloxy group found on psilocybin with an acetoxy group, is also readily available. The substituted acetoxy group is believed to be metabolized in an equivalent manner to the phosphoryloxy group, both producing psilocin during first-pass metabolism.37 This simple modification skirts written laws in the United States when the product is clearly designated "not for human consumption," allowing pseudolegal import and possession for research purposes only; however, if it were to be used in vivo, the user would be in violation of the Federal Analogue Act.38 Although psilacetin has been hypothesized to act as an identical pharmacological substitute for psilocybin, many users report a small, yet significant, difference in the effects of each drug.39 Psilacetin is often described as having a faster onset of action without the anxiety and nausea associated with psilocybin-containing mushroom ingestion (which could be due to avoiding the ingestion of the significant amounts of chitin usually found in these mushrooms) and to have a shorter duration of action with a more peaceful experience throughout, leaving most users with a positive afterglow.37,39
  2. ^ a b c d e f g h i j Jones NT, Wagner L, Hahn MC, Scarlett CO, Wenthur CJ (2024). "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.
  3. ^ a b c d 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.
  4. ^ a b c Wright W (24 June 2024). "4-AcO-DMT Is the Most Accessible (and Mysterious) Drug on the Market Right Now". DoubleBlind Mag. Retrieved 2 February 2025.
  5. ^ a b c d e 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. 4-AcO-DMT (4-acetoxyN,N-dimethyltryptamine, O-acetylpsilocin, or psilacetin) was the most prevalent tryptamine reported with 30.8% of the sample reporting use and two thirds (66.7%) of tryptamine users reporting use. 4-AcO-DMT—often pronounced as "4-akko-DMT"—was reported by most users as producing similar effects as psilocybin mushrooms with less nausea. One participant referred to this compound as "silly pills," which is a play on the name psilocybin. This particular compound was often preferred over natural mushrooms due to the lack of adverse side effects such as nausea, which the natural mushroom tends to produce. Thus, participants often suggested that 4-AcODMT allows one to achieve the same high as psilocybin without adverse physical effects such as nausea and heavy body load. One participant did complain of dry mouth and mentioned that although 4-AcO-DMT feels similar to psilocybin, he said it lacks the "organic" feel produced by psilocybin. [...] Of the most common tryptamines used by this sample, the majority of these compounds were first discovered or first synthesized as early as the 1930s (e.g., 5-MeO-DMT), 1950s (e.g., 4-AcO-DMT), or in the 1970s (e.g., 4-HO-MET and 5-MeO-DIPT). [...] 4-AcO-DMT was the most commonly used tryptamine by participants, and this compound also appears to be among the most prevalent novel tryptamines in recent years (Palamar & Le, 2019; PalmaConesa et al., 2017). [...] 4-AcO-DMT is often described as having a faster onset of action than psilocybin with a high of shorter duration, and as many of our participants noted, use allows them to avoid the nausea commonly associated mushroom ingestion (Geiger et al., 2018). Despite 4-AcO-DMT being among the most prevalent tryptamines, and having been discovered in the 1950s, little academic research has focused on recreational use of this compound.
  6. ^ a b c d Cite error: The named reference KleinChathaLaskowski2021 was invoked but never defined (see the help page).
  7. ^ Halberstadt AL (January 2015). "Recent advances in the neuropsychopharmacology of serotonergic hallucinogens". Behav Brain Res. 277: 99–120. doi:10.1016/j.bbr.2014.07.016. PMC 4642895. PMID 25036425.
  8. ^ Kwan AC, Olson DE, Preller KH, Roth BL (November 2022). "The neural basis of psychedelic action". Nat Neurosci. 25 (11): 1407–1419. doi:10.1038/s41593-022-01177-4. PMC 9641582. PMID 36280799.
  9. ^ a b Blakinger K, Sheets C (9 August 2024). "Magic mushroom chocolates are having a moment. But do they even contain mushrooms?". Los Angeles Times. Retrieved 1 February 2025.
  10. ^ Ovalle D (4 July 2024). "Psychedelic mushroom edibles promise health benefits. Be wary, experts say". Washington Post. Archived from the original on 4 July 2024. Retrieved 1 February 2025.
  11. ^ Syal A (18 July 2024). "Mushroom edibles are rising in popularity. It's hard to say what's in them". NBC News. Retrieved 1 February 2025.
  12. ^ a b Ducharme J (4 October 2024). "Are Mushroom Edibles Safe and Legal?". TIME. Retrieved 1 February 2025.
  13. ^ Mole B (5 July 2024). "What we know about microdosing candy illnesses as death investigation underway". Ars Technica. Retrieved 1 February 2025.
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