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4-AcO-MET

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
4-AcO-MET
Clinical data
Other names4-Acetoxy-MET; 4-Acetoxy-N-methyl-N-ethyltryptamine; Metacetin
Legal status
Legal status
Identifiers
  • [3-[2-[ethyl(methyl)amino]ethyl]-1H-indol-4-yl] acetate
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC15H20N2O2
Molar mass260.337 g·mol−1
3D model (JSmol)
  • CCN(C)CCc1c[nH]c2c1c(ccc2)OC(=O)C
  • InChI=1S/C15H20N2O2/c1-4-17(3)9-8-12-10-16-13-6-5-7-14(15(12)13)19-11(2)18/h5-7,10,16H,4,8-9H2,1-3H3
  • Key:OMDKHOOGGJRLLX-UHFFFAOYSA-N

4-AcO-MET, also known as4-acetoxy-N-methyl-N-ethyltryptamine ormetacetin, is apsychedelic drug of thetryptamine family. It is theacetateester of4-HO-MET, and ahomologue of4-AcO-DMT. It is a novel compound with very little history of human use.[2] It is sometimes sold as aresearch chemical by online retailers.

Pharmacology

[edit]

Due to its similarity to thepsilocinprodrug 4-AcO-DMT, which isdeacetylated to form psilocinin vivo,[3][4] it is expected that 4-AcO-MET is also quicklyhydrolyzed into4-HO-MET byserumesterases, but human studies concerning themetabolic fate of this drug are lacking.

Thepharmacology of 4-AcO-MET has been studied.[5][6]

Legal status

[edit]

Switzerland

[edit]

In Switzerland, 4-Acetoxy-MET is a controlled substance under Verzeichnis E.[7]

United Kingdom

[edit]

In the United Kingdom, 4-AcO-MET is a Class A drug in the United Kingdom because it is anester of the drug 4-HO-MET, which is a Class A drug under the tryptamine catch-all clause.[8]

United States

[edit]

In the United States, 4-Acetoxy-MET is not scheduled. It may be considered an analogue ofpsilocin, a Schedule I drug under theControlled Substances Act. As such, the sale for human consumption or the use for illicit non-medical purposes could be considered a crime under the Federal Analogue Act.[9]

References

[edit]
  1. ^Anvisa (2024-05-28)."RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União.Archived from the original on 2024-09-25. Retrieved2024-09-25.
  2. ^"New psychoactive substances reported to the EMCDDA and Europol for the first time in 2009 under the terms of Council Decision 2005/387/JHA"(PDF).www.emcdda.europa.eu. Retrieved6 May 2022.
  3. ^Nichols DE (February 1999)."Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin".Synthesis.1999 (6):935–938.doi:10.1055/s-1999-3490.S2CID 32044725.
  4. ^Pham DN, Chadeayne AR, Golen JA, Manke DR (February 2021)."Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrug".Acta Crystallographica Section E.77 (Pt 2):101–106.Bibcode:2021AcCrE..77..101P.doi:10.1107/S2056989021000116.PMC 7869532.PMID 33614134.
  5. ^Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH (April 2023)."Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice".ACS Pharmacol Transl Sci.6 (4):567–577.doi:10.1021/acsptsci.2c00222.PMC 10111620.PMID 37082754.
  6. ^Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL (April 2021)."Investigation of the Structure-Activity Relationships of Psilocybin Analogues".ACS Pharmacol Transl Sci.4 (2):533–542.doi:10.1021/acsptsci.0c00176.PMC 8033608.PMID 33860183.
  7. ^"Fedlex".www.fedlex.admin.ch. Retrieved2021-08-15.
  8. ^"Misuse of Drugs Act 1971". 2021-08-15.Archived from the original on 2012-11-11.
  9. ^"21 U.S. Code § 841 - Prohibited acts A",LII / Legal Information Institute, retrieved2016-08-02
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