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Methoxetamine

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Not to be confused with methoxamine.
Methoxetamine
Clinical data
ATC code
  • None
Identifiers
  • (RS)2-(3-methoxyphenyl)-2-(ethylamino)cyclohexanone[1]
CAS Number
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21NO2
Molar mass247.33 g/mol g·mol−1
3D model (JSmol)
  • O=C1CCCCC1(NCC)c2cccc(c2)OC
  • 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 checkY
  • Key:LPKTWLVEGBNOOX-UHFFFAOYSA-N checkY
  (verify)

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][3] Methoxetamine differs from many other dissociative anesthetics of the arylcyclohexylamine class in that it was designed for grey market distribution.[4] Methoxetamine is a product of rational drug design: its N-ethyl group was chosen to increase potency.[4] Slang names include sparklepoofies and M-Ket, as well as two names which are primarily media manufactures: roflcoptr and mexxie. Of those, mexxie is on rare occasions now used outside of the media, but roflcoptr is generally only used in a manner mocking the riduculousness of the media coverage.

Physical properties

Pure methoxetamine is a white powder.[5] It has low solubility in isopropanol, 6 mg mL-1 at -10°C.[6]

Emergence

The European Monitoring Centre for Drugs and Drug Addiction, which monitors the internet for new psychoactive substances within the European Union, first identified methoxetamine in November 2010.[1] By July 2011, they had identified 58 websites selling the compound, at a cost of 145–195 euros for 10 grams.[7]

Effects

It is reported to have similar desirable and unwanted effects to ketamine, although some users have reported that the unwanted effects last longer than for ketamine.[8] Little is known about the potential toxicity of methoxetamine, but people have been hospitalized in the US and UK after using it recreationally.[3][9][10] Acute cerebellar toxicity has been documented in three cases of hospital admission due to methoxetamine overdose, lasting for between one and four days after exposure.[10]

Methoxetamine has been marketed as "bladder friendly", referencing the bladder damage associated with chronic ketamine use, but further scientific research is required to determine whether this is the case.[9][11] From the limited information available based on user reports on internet discussion forums, toxicologists have stated it has "potential to be associated with significant acute harm/toxicity if used as a recreational drug."[8]

Consistent with other NMDA antagonsists, it is thought that methoxetamine may be an effective, fast-acting antidepressant. Its activity at other receptors may contribute to this.[12]

Methoxetamine powder
Theresa May commented in her reply to the ACMD that "the next step in this process is for the ACMD to undertake a full assessment of methoxetamine for consideration for its permanent control under the 1971 Act." She goes on to say that she hopes the ACMD will do this as a part of the review of ketamine, "including its analogues" and that this review will be completed "within the 12 months from the making of the current order".[18]

Media coverage

Mixmag reported in January 2012, that people in the dance music and clubbing community have given methoxetamine the slang name 'roflcoptr'.[22] Vice commented that it was likely that the phrase will only be used by "the same politicians, parents and journalists" who called mephedrone 'meow meow'.[23] In fact, the name roflcoptr was created by a mysterious vendor at www.roflcoptr.co.uk, though it was later found that the owner of this domain name was also responsible for press releases that led to the Mixmag and other media coverages. It has been the subject of some speculation whether this was a shamelessly self-promoting vendor, or a media outlet creating a fake site in order to subsequently write scandalous sounding media scare stories. After being called mexxy in UK Home Office press releases users and the media adopted the name[24] despite this being an uncommon term before its receiving media attention.[25]

A literature review was published in March 2012 which looked at scientific literature and information on the web. It concluded that "the online availability of information on novel psychoactive drugs, such as methoxetamine, may constitute a pressing public health challenge. Better international collaboration levels and novel forms of intervention are necessary to tackle this fast-growing phenomenon."[26]

See also

References

  1. ^ a b c EMCDDA Annual Report 2010 (PDF) (Report). European Monitoring Centre for Drugs and Drug Addiction. 2010. Retrieved 23 January 2012.
  2. ^ Hays, P. A.; Casale, J. F.; Berrier, A. L. (2012). "The Characterization of 2-(3-Methoxyphenyl)-2-(ethylamino)cyclohexanone (Methoxetamine)" (pdf). Microgram Journal. 9 (1): 3–17.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ a b 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.
  4. ^ a b Morris, H. (11 February 2011). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Retrieved 23 January 2012.
  5. ^ "Methoxetamine FRANK". Retrieved 14 April 2012.
  6. ^ "The Big & Dandy Methoxetamine Thread: 9th dose - Tolerance Schmolerance". 12 April 2012. Retrieved 14 April 2012.
  7. ^ Online sales of new psychoactive substances/‘legalhighs’: Summary of results from the 2011 multilingual snapshots (PDF) (Report). European Monitoring Centre for Drugs and Drug Addiction. 15 November 2011. Retrieved 23 January 2012.
  8. ^ a b Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1093/qjmed/hcr191, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1093/qjmed/hcr191 instead.
  9. ^ a b Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1007/s00228-011-1199-9 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1007/s00228-011-1199-9 instead.
  10. ^ a b Template:Cite DOI
  11. ^ Daly, M.; Simonson, P. (November 2011). "Street drug trends survey 2011" (PDF). Drugscope. Retrieved 3 January 2012.{{cite web}}: CS1 maint: multiple names: authors list (link)
  12. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/j.mehy.2012.07.002 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1016/j.mehy.2012.07.002 instead.
  13. ^ McPherson, P. (13 February 2012). "Health alert over drug sold as 'safe ketamine'". London: The Independent. Retrieved 18 February 2012.
  14. ^ http://www.homeoffice.gov.uk/media-centre/news/mexxy
  15. ^ Johnson, Wesley (6 March 2012). "Bid to ban 'safe' drug Methoxetamine after deaths". The Independent. London. Retrieved 12 May 2012.
  16. ^ "Statement of evidence - methoxetamine" (PDF). UK Home Office. 23 February 2012. Retrieved 29 March 2012.
  17. ^ "Methoxetamine". Home Office UK. Retrieved 17 May 2012.
  18. ^ "Home Secretary's response to the ACMD's advice on methoxetamine". UK Home Office. 28 March 2012. Retrieved 28 March 2012.
  19. ^ "Resolution of the Government of the Russian Federation on October 6, 2011 N 822". Retrieved 20 February 2012. Template:Ru icon
  20. ^ "Ordinance on the lists of narcotic drugs, psychotropic substances, precursors and auxiliary chemicals". Retrieved 20 February 2012. Template:De icon
  21. ^ "薬事法指定薬物　東京都福祉保健局". Retrieved 25 June 2012. Template:Ja icon
  22. ^ Beaumont-Thomas, B. (18 January 2012). "Methoxetamine is a new chemical analogue of ketamine. It's legal, it's cheap and it's trippy as hell - but is it safe?". No. 249. London, UK: Mixmag. p. 60.
  23. ^ Miller, A. (11 February 2011). "We Interviewed the Inventor of Roflcoptr, the New Drug Britain's Panicking About". Vice Magazine. Retrieved 11 February 2011.
  24. ^ "Legal high drug 'mexxy' banned under new government powers". The Guardian. London. 28 March 2012.
  25. ^ "Methoxetamine information". 13 April 2012. Retrieved 12 May 2012.
  26. ^ Template:Cite DOI
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