4-AcO-MET
{{Short description|Chemical compound}}
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{{Infobox drug
| drug_name = 4-AcO-MET
| image = 4-Acetoxy-N-methyl-N-ethyltryptamine.svg
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| legal_BR = F2
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2024-05-28 |title=RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-da-diretoria-colegiada-anvisa-n-877-de-28-de-maio-de-2024-562758149 |url-status=live |archive-url=https://web.archive.org/web/20240925040323/https://www.in.gov.br/en/web/dou/-/resolucao-da-diretoria-colegiada-anvisa-n-877-de-28-de-maio-de-2024-562758149 |archive-date=2024-09-25 |access-date=2024-09-25 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2024-05-28}}
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| CAS_number = 1445751-40-5
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| PubChem = 71308138
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| ChemSpiderID = 26633897
| UNII = PCJ17NV1P0
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| synonyms = 4-Acetoxy-MET; 4-Acetoxy-N-methyl-N-ethyltryptamine; Metacetin
| IUPAC_name = [3-[2-[ethyl(methyl)amino]ethyl]-1H-indol-4-yl] acetate
| C=15 | H=20 | N=2 | O=2
| SMILES = CCN(C)CCc1c[nH]c2c1c(ccc2)OC(=O)C
| StdInChI = 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
| StdInChIKey = 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.{{cite web|title=New psychoactive substances reported to the EMCDDA and Europol for the first time in 2009 under the terms of Council Decision 2005/387/JHA|url=https://www.emcdda.europa.eu/attachements.cfm/att_101538_EN_Annex%202.pdf|website=www.emcdda.europa.eu|access-date=6 May 2022}} It is sometimes sold as a research chemical by online retailers.
Pharmacology
Due to its similarity to the psilocin prodrug 4-AcO-DMT, which is deacetylated to form psilocin in vivo,{{cite journal | vauthors = Nichols DE | date = February 1999 |title= Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin |url=http://www.thieme-connect.de/DOI/DOI?10.1055/s-1999-3490 |journal=Synthesis |volume=1999 |issue=6 |pages=935–938 |doi=10.1055/s-1999-3490| s2cid = 32044725 |url-access=subscription }}{{cite journal | vauthors = Pham DN, Chadeayne AR, Golen JA, Manke DR | title = Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrug | journal = Acta Crystallographica Section E | volume = 77 | issue = Pt 2 | pages = 101–106 | date = February 2021 | pmid = 33614134 | pmc = 7869532 | doi = 10.1107/S2056989021000116 | bibcode = 2021AcCrE..77..101P }} 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.{{cite journal | vauthors = Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH | title = Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice | journal = ACS Pharmacol Transl Sci | volume = 6 | issue = 4 | pages = 567–577 | date = April 2023 | pmid = 37082754 | pmc = 10111620 | doi = 10.1021/acsptsci.2c00222 | url = }}{{cite journal | vauthors = Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL | title = Investigation of the Structure-Activity Relationships of Psilocybin Analogues | journal = ACS Pharmacol Transl Sci | volume = 4 | issue = 2 | pages = 533–542 | date = April 2021 | pmid = 33860183 | pmc = 8033608 | doi = 10.1021/acsptsci.0c00176 | url = }}
Society and culture
=Legal status=
==Switzerland==
In Switzerland, 4-Acetoxy-MET is a controlled substance under Verzeichnis E.{{cite web|title=Fedlex|url=https://www.fedlex.admin.ch/eli/cc/2011/363/de|access-date=2021-08-15|website=www.fedlex.admin.ch}}
==United Kingdom==
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.{{cite web|date=2021-08-15|title=Misuse of Drugs Act 1971|url=https://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I|url-status=live|archive-url = https://web.archive.org/web/20121111193914/http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I |archive-date = 2012-11-11 }}
==United States==
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.{{cite web |title=21 U.S. Code § 841 - Prohibited acts A |url=https://www.law.cornell.edu/uscode/text/21/841 |access-date=2016-08-02 |website=LII / Legal Information Institute |mode=cs2}}
References
{{Reflist}}
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Tryptamines}}
{{DEFAULTSORT:Acetoxy-MET, 4-}}
Category:N,N-Dialkyltryptamines
Category:Psychedelic tryptamines