Methoxetamine: Difference between revisions

Methoxetamine
Clinical data
ATC code	None;
Identifiers
	IUPAC name (RS)2-(3-methoxyphenyl)-2-(ethylamino)cyclohexanone;
CAS Number	1239943-76-0 ;
ChemSpider	24721792 ;
CompTox Dashboard (EPA)	DTXSID301009327 ;
Chemical and physical data
Formula	C15H21NO2
Molar mass	247.33 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1CCCCC1(NCC)c2cccc(c2)OC;
	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 ;
	(verify)

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Revision as of 23:54, 17 November 2011

Methoxetamine (MXE) or 3-MeO-2-Oxo-PCE is a chemical of the arylcyclohexylamine class which has been sold as a designer drug.^[1] It is a derivative of ketamine that also contains structural features of eticyclidine and 3-MeO-PCP. Methoxetamine is thought to behave as a NMDA receptor antagonist and dopamine reuptake inhibitor, though it has not been formally profiled pharmacologically.^[2] Methoxetamine differs from many other dissociative anesthetics of the arylcyclohexylamine class in that it was designed for grey-market distribution.^[3] Methoxetamine is a product of rational drug design: its N-ethyl group was chosen to increase potency, lessening the risk of interstitial cystitis that can result from the accumulation of ketamine-like metabolites in the urinary bladder.^[3]^[4]

References

^ EMCDDA Annual Report 2010
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.3109/15563650.2011.617310, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.3109/15563650.2011.617310 instead.
^ ^a ^b [1], Morris, H. (11 February 2011). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Retrieved 2011-02-11.
^ "4-Amino-4-arylcyclohexanones and Their Derivatives, a Novel Class of Analgesics. 1. Modification of the Aryl Ring." Daniel Lednicer, Philip F. VonVoigtlander and D. Edward Emmert. The Upjohn Company, Research Laboratories, Kalamazoo, Michigan 49001. Received August 7, 1979. J. Med. Chem 1980, 23, p424-430

External links

Erowid.org – Methoxetamine Information

[1] EMCDDA Annual Report 2010

[2] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.3109/15563650.2011.617310, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.3109/15563650.2011.617310 instead.

[Interview_with_a_ketamine_chemist-3] [1], Morris, H. (11 February 2011). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Retrieved 2011-02-11.

[4] "4-Amino-4-arylcyclohexanones and Their Derivatives, a Novel Class of Analgesics. 1. Modification of the Aryl Ring." Daniel Lednicer, Philip F. VonVoigtlander and D. Edward Emmert. The Upjohn Company, Research Laboratories, Kalamazoo, Michigan 49001. Received August 7, 1979. J. Med. Chem 1980, 23, p424-430

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-'''Methoxetamine (MXE)''' or '''3-MeO-2-Oxo-PCE''' is a chemical of the [[arylcyclohexylamine]] class which has been sold as a [[designer drug]].<ref>[http://www.emcdda.europa.eu/attachements.cfm/att_132857_EN_EMCDDA-Europol%20Annual%20Report%202010A.pdf EMCDDA Annual Report 2010]</ref> It is a derivative of [[ketamine]] that also contains structural features of [[eticyclidine]] and [[3-MeO-PCP]]. Methoxetamine is thought to behave as a [[NMDA receptor antagonist]] and [[dopamine reuptake inhibitor]], though it has not been formally profiled pharmacologically.<ref>{{Cite doi|10.3109/15563650.2011.617310}}</ref> Methoxetamine differs from many other dissociative anesthetics of the arylcyclohexylamine class in that it was designed for grey-market distribution.<ref name="Interview with a ketamine chemist">[http://www.viceland.com/int/v18n2/htdocs/interview-with-ketamine-chemist-704.php?page=1], Morris, H. (11 February 2011). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Retrieved 2011-02-11.</ref> Methoxetamine is a product of rational [[drug design]]: its N-ethyl group was chosen to increase potency, lessening the risk of [[interstitial cystitis]] that can result from the accumulation of ketamine-like metabolites in the urinary bladder.<ref name="Interview with a ketamine chemist">[http://www.viceland.com/int/v18n2/htdocs/interview-with-ketamine-chemist-704.php?page=1], Morris, H. (11 February 2011). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Retrieved 2011-02-11.</ref> However, this appears to additionally make methoxetamine a highly potent opioid prodrug as well.<ref>"4-Amino-4-arylcyclohexanones and Their Derivatives, a Novel Class of Analgesics. 1. Modification of the Aryl Ring." Daniel Lednicer, Philip F. VonVoigtlander and D. Edward Emmert. The Upjohn Company, Research Laboratories, Kalamazoo, Michigan 49001. Received August 7, 1979. J. Med. Chem 1980, 23, p424-430</ref> Widespread reports of use in 2011.
+'''Methoxetamine (MXE)''' or '''3-MeO-2-Oxo-PCE''' is a chemical of the [[arylcyclohexylamine]] class which has been sold as a [[designer drug]].<ref>[http://www.emcdda.europa.eu/attachements.cfm/att_132857_EN_EMCDDA-Europol%20Annual%20Report%202010A.pdf EMCDDA Annual Report 2010]</ref> It is a derivative of [[ketamine]] that also contains structural features of [[eticyclidine]] and [[3-MeO-PCP]]. Methoxetamine is thought to behave as a [[NMDA receptor antagonist]] and [[dopamine reuptake inhibitor]], though it has not been formally profiled pharmacologically.<ref>{{Cite doi|10.3109/15563650.2011.617310}}</ref> Methoxetamine differs from many other dissociative anesthetics of the arylcyclohexylamine class in that it was designed for grey-market distribution.<ref name="Interview with a ketamine chemist">[http://www.viceland.com/int/v18n2/htdocs/interview-with-ketamine-chemist-704.php?page=1], Morris, H. (11 February 2011). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Retrieved 2011-02-11.</ref> Methoxetamine is a product of rational [[drug design]]: its N-ethyl group was chosen to increase potency, lessening the risk of [[interstitial cystitis]] that can result from the accumulation of ketamine-like metabolites in the urinary bladder.<ref name="Interview with a ketamine chemist">[http://www.viceland.com/int/v18n2/htdocs/interview-with-ketamine-chemist-704.php?page=1], Morris, H. (11 February 2011). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Retrieved 2011-02-11.</ref><ref>"4-Amino-4-arylcyclohexanones and Their Derivatives, a Novel Class of Analgesics. 1. Modification of the Aryl Ring." Daniel Lednicer, Philip F. VonVoigtlander and D. Edward Emmert. The Upjohn Company, Research Laboratories, Kalamazoo, Michigan 49001. Received August 7, 1979. J. Med. Chem 1980, 23, p424-430</ref>
 ==See also==