Methoxetamine

Methoxetamine
Clinical data
Other names	MXE; 3-MeO-2'-oxo-PCE
Addiction; liability	High
Drug class	NMDA receptor antagonists; Dissociative hallucinogens; General anesthetics
ATC code	None;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); DE: Anlage I (Authorized scientific use only); UK: Class B; US: Schedule I (as of July 6, 2022); UN: Psychotropic Schedule II;
Pharmacokinetic data
Elimination half-life	3–6 hours
Identifiers
	IUPAC name (R/S)-2-(3-Methoxyphenyl)-2-(ethylamino)cyclohexanone;
CAS Number	1239943-76-0 ;
PubChem CID	52911279;
ChemSpider	24721792 ;
UNII	ZO5ZCE6E12;
KEGG	C22711;
CompTox Dashboard (EPA)	DTXSID301009327 ;
Chemical and physical data
Formula	C15H21NO2
Molar mass	247.338 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1CCCCC1(C2=CC=CC(OC)=C2)NCC;
	InChI InChI=1S/C15H21NO2/c1-3-16-15(10-5-4-9-14(15)17)12-7-6-8-13(11-12)18-2/h6-8,11,16H,3-5,9-10H2,1-2H3 ; Key:LPKTWLVEGBNOOX-UHFFFAOYSA-N ;
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Methoxetamine, abbreviated as MXE, is a dissociative hallucinogen that has been sold as a designer drug.^[5]^[6] It differs from many dissociatives such as ketamine and phencyclidine (PCP) that were developed as pharmaceutical drugs for use as general anesthetics in that it was designed specifically to increase the antidepressant effects of ketamine.^[6]^[7]

MXE is an arylcyclohexylamine.^[8] It acts mainly as an NMDA receptor antagonist, similarly to other arylcyclohexylamines like ketamine and PCP.^[8]

^ Kjellgren A, Jonsson K (2013). "Methoxetamine (MXE)--a phenomenological study of experiences induced by a "legal high" from the internet". Journal of Psychoactive Drugs. 45 (3): 276–286. doi:10.1080/02791072.2013.803647. PMC 3756617. PMID 24175493.
^ "Federal Register". FederalRegister.gov. Retrieved 21 June 2022.
^ Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
^ "Substance Details Methoxetamine". Retrieved 22 January 2024.
^ ^a ^b EMCDDA Annual Report 2010 (PDF) (Report). European Monitoring Centre for Drugs and Drug Addiction. 2010. Archived (PDF) from the original on 14 March 2012. Retrieved 23 January 2012.
^ ^a ^b Morris H, Wallach J (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–632. doi:10.1002/dta.1620. PMID 24678061.
^ Morris H (11 February 2011). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Archived from the original on 30 January 2012. Retrieved 23 January 2012.
^ ^a ^b Cite error: The named reference pmid23527166 was invoked but never defined (see the help page).

[Methoxetamine_MXE--a_phenomenolog-1] Kjellgren A, Jonsson K (2013). "Methoxetamine (MXE)--a phenomenological study of experiences induced by a "legal high" from the internet". Journal of Psychoactive Drugs. 45 (3): 276–286. doi:10.1080/02791072.2013.803647. PMC 3756617. PMID 24175493.

[2] "Federal Register". FederalRegister.gov. Retrieved 21 June 2022.

[3] Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.

[4] "Substance Details Methoxetamine". Retrieved 22 January 2024.

[emcdda-5] EMCDDA Annual Report 2010 (PDF) (Report). European Monitoring Centre for Drugs and Drug Addiction. 2010. Archived (PDF) from the original on 14 March 2012. Retrieved 23 January 2012.

[Morris-6] Morris H, Wallach J (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–632. doi:10.1002/dta.1620. PMID 24678061.

[Interview_with_a_ketamine_chemist-7] Morris H (11 February 2011). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Archived from the original on 30 January 2012. Retrieved 23 January 2012.

[pmid23527166-8] Cite error: The named reference pmid23527166 was invoked but never defined (see the help page).

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Clinical data


Other names	MXE; 3-MeO-2'-oxo-PCE
Addiction liability	High^[1]
Drug class	NMDA receptor antagonists; Dissociative hallucinogens; General anesthetics
ATC code	None
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)^[3] DE: Anlage I (Authorized scientific use only) UK: Class B US: Schedule I (as of July 6, 2022)^[2] UN: Psychotropic Schedule II^[4]
Pharmacokinetic data
Elimination half-life	3–6 hours
Identifiers
IUPAC name (R/S)-2-(3-Methoxyphenyl)-2-(ethylamino)cyclohexanone^[5]
CAS Number	1239943-76-0^Y
PubChem CID	52911279
ChemSpider	24721792^Y
UNII	ZO5ZCE6E12
KEGG	C22711
CompTox Dashboard (EPA)	DTXSID301009327
Chemical and physical data
Formula	C₁₅H₂₁NO₂
Molar mass	247.338 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C1CCCCC1(C2=CC=CC(OC)=C2)NCC
InChI InChI=1S/C15H21NO2/c1-3-16-15(10-5-4-9-14(15)17)12-7-6-8-13(11-12)18-2/h6-8,11,16H,3-5,9-10H2,1-2H3^Y Key:LPKTWLVEGBNOOX-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)