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4-AcO-MET

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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
PubChem CID
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 as 4-acetoxy-N-methyl-N-ethyltryptamine or metacetin, is a psychedelic drug of the tryptamine family. It is the acetate ester of 4-HO-MET, and a homologue of 4-AcO-DMT. It is a novel compound with very little history of human use.[2] It is sometimes sold as a research chemical by online retailers.

Pharmacology

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Due to its similarity to the psilocin prodrug 4-AcO-DMT, which is deacetylated to form psilocin in vivo,[3][4] it is expected that 4-AcO-MET is also quickly hydrolyzed into 4-HO-MET by serum esterases, but human studies concerning the metabolic fate of this drug are lacking.

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

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Switzerland

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

United Kingdom

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

United States

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In the United States, 4-Acetoxy-MET is not scheduled. It may be considered an analogue of psilocin, a Schedule I drug under the Controlled 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

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  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. Retrieved 2024-09-25.
  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. Retrieved 6 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. Retrieved 2021-08-15.
  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, retrieved 2016-08-02
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