Methoxetamine

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Methoxetamine
Systematic (IUPAC) name
(RS)2-(3-methoxyphenyl)-2-(ethylamino)cyclohexanone[1]
Clinical data
Legal status ?
Pharmacokinetic data
Half-life3-6 hours.
Identifiers
CAS number1239943-76-0 YesY
ATC codeNone
ChemSpider24721792 YesY
Chemical data
FormulaC15H21NO2 
Mol. mass247.33 g/mol
 YesY (what is this?)  (verify)
 
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Methoxetamine
Systematic (IUPAC) name
(RS)2-(3-methoxyphenyl)-2-(ethylamino)cyclohexanone[1]
Clinical data
Legal status ?
Pharmacokinetic data
Half-life3-6 hours.
Identifiers
CAS number1239943-76-0 YesY
ATC codeNone
ChemSpider24721792 YesY
Chemical data
FormulaC15H21NO2 
Mol. mass247.33 g/mol
 YesY (what is this?)  (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 has been shown to act as an NMDA receptor antagonist and serotonin reuptake inhibitor.[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.[3]

Physical properties[edit]

Pure methoxetamine hydrochloride is a white powder.[4] It has low solubility in isopropanol, 6 mg/mL at -10°C.[5] It is soluble in ethanol, 10 mg/ml at 25°C.[6]

Emergence[edit]

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[edit]

It is reported to have similar desirable and unwanted effects to ketamine,[8] although some users have reported that the unwanted effects last longer than for ketamine.[9] Little is known about the potential toxicity of methoxetamine, but people have been hospitalized in the US and UK after using it recreationally.[10][11] Acute reversible cerebellar toxicity has been documented in three cases of hospital admission due to methoxetamine overdose, lasting for between one and four days after exposure.[11]

Methoxetamine has been marketed as "bladder friendly", referencing the bladder damage associated with chronic ketamine use, but the reasoning behind this seems to have been based purely on the increased potency of methoxetamine compared to ketamine and further scientific research is required to determine whether this is actually the case.[10][12] 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."[9]

It is thought that methoxetamine may be an effective, fast-acting antidepressant like other NMDA antagonists. Its activity at other receptors may contribute to this.[13]

Legal status[edit]

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".[19]
On October 18th 2012 the ACMD released a report about MXE, saying that the "harms of methoxetamine are commensurate with Class B of the Misuse of Drugs Act (1971)", despite the fact that the act does not classify drugs based on harm. The report went on to suggest that all analogues of MXE should also become class B drugs and suggested a catch-all clause covering both existing and unresearched arylcyclohexamines.
MXE ceased to be covered by the temporary prohibition on 26 February 2013, when it became classified as a Class B drug. [20]

Media coverage[edit]

Mixmag reported in January 2012, that people in the dance music and clubbing community have given methoxetamine the slang name 'roflcoptr'.[25] 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'.[26] After being called mexxy in UK Home Office press releases, the media adopted the name.[27]

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."[28]

Detection[edit]

A forensic standard of Methoxetamine is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[29]

See also[edit]

References[edit]

  1. ^ a b c EMCDDA Annual Report 2010 (Report). European Monitoring Centre for Drugs and Drug Addiction. 2010. http://www.emcdda.europa.eu/attachements.cfm/att_132857_EN_EMCDDA-Europol%20Annual%20Report%202010A.pdf. Retrieved 2012-01-23.
  2. ^ "ACMD Methoxetamine Report (2012)". Advisory Council on the Misuse of Drugs. October 2012. pp. 14–15. Retrieved 6 February 2013. 
  3. ^ a b Morris, H. (2011-02-11). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Retrieved 2012-01-23. 
  4. ^ "Methoxetamine FRANK". Retrieved 2012-04-14. 
  5. ^ "The Big & Dandy Methoxetamine Thread: 9th dose - Tolerance Schmolerance". 2012-04-12. Retrieved 2012-04-14. 
  6. ^ https://www.caymanchem.com/msdss/11139m.pdf
  7. ^ Online sales of new psychoactive substances/‘legalhighs’: Summary of results from the 2011 multilingual snapshots (Report). European Monitoring Centre for Drugs and Drug Addiction. 2011-11-15. http://www.emcdda.europa.eu/attachements.cfm/att_143801_EN_SnapshotSummary.pdf. Retrieved 2012-01-23.
  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. doi:10.1080/02791072.2013.803647. 
  9. ^ a b Wood, D. M.; Davies, S.; Calapis, A.; Ramsey, J.; Dargan, P. I. (2011). "Novel Drugs -- Novel Branding". QJM. doi:10.1093/qjmed/hcr191. PMID 21997441.  edit
  10. ^ a b Wood, D. M.; Davies, S.; Puchnarewicz, M.; Johnston, A.; Dargan, P. I. (2011). "Acute toxicity associated with the recreational use of the ketamine derivative methoxetamine". European Journal of Clinical Pharmacology 68 (5): 853–856. doi:10.1007/s00228-011-1199-9. PMID 22205276.  edit
  11. ^ a b Shields, J. E.; Dargan, P. I.; Wood, D. M.; Puchnarewicz, M.; Davies, S.; Waring, W. S. (2012). "Methoxetamine associated reversible cerebellar toxicity: Three cases with analytical confirmation". Clinical Toxicology 50 (5): 438–440. doi:10.3109/15563650.2012.683437. PMID 22578175.  edit
  12. ^ Daly, M.; Simonson, P. (November 2011). "Street drug trends survey 2011". Drugscope. Retrieved 2012-01-03. 
  13. ^ Coppola, M.; Mondola, R. (2012). "Methoxetamine: From drug of abuse to rapid-acting antidepressant". Medical Hypotheses. doi:10.1016/j.mehy.2012.07.002.  edit
  14. ^ McPherson, P. (2012-02-13). "Health alert over drug sold as 'safe ketamine'". London: The Independent. Retrieved 2012-02-18. 
  15. ^ http://www.homeoffice.gov.uk/media-centre/news/mexxy
  16. ^ Johnson, Wesley (2012-03-06). "Bid to ban 'safe' drug Methoxetamine after deaths". The Independent (London). Retrieved 2012-05-12. 
  17. ^ "Statement of evidence - methoxetamine" (PDF). UK Home Office. 2012-02-23. Retrieved 2012-03-29. 
  18. ^ "Methoxetamine". Home Office UK. Retrieved 2012-05-17. 
  19. ^ "Home Secretary's response to the ACMD's advice on methoxetamine". UK Home Office. 2012-03-28. Retrieved 2012-03-28. 
  20. ^ "Home Office circular 004-2013". UK Home Office. 2013-02-20. Retrieved 2013-02-27. 
  21. ^ "Resolution of the Government of the Russian Federation on October 6, 2011 N 822". Retrieved 2012-02-20.  (Russian)
  22. ^ "Ordinance on the lists of narcotic drugs, psychotropic substances, precursors and auxiliary chemicals". Retrieved 2012-02-20.  (German)
  23. ^ "薬事法指定薬物 東京都福祉保健局". Retrieved 2012-06-25.  (Japanese)
  24. ^ "Narkotika-klassning av sex nya substanser". Retrieved 2013-11-26.  (Swedish)
  25. ^ Beaumont-Thomas, B. (2012-01-18). "Methoxetamine is a new chemical analogue of ketamine. It's legal, it's cheap and it's trippy as hell - but is it safe?" (249). London, UK: Mixmag. p. 60. 
  26. ^ Miller, A. (2011-02-11). "We Interviewed the Inventor of Roflcoptr, the New Drug Britain's Panicking About". Vice Magazine. Retrieved 2011-02-11. 
  27. ^ "Legal high drug 'mexxy' banned under new government powers". The Guardian (London). 28 March 2012. 
  28. ^ Corazza, O. et al. (2012). "Phenomenon of New Drugs on the Internet: The Case of Ketamine Derivative Methoxetamine". Human Psychopharmacology: Clinical and Experimental 27 (2): 145–149. doi:10.1002/hup.1242. PMID 22389078.  edit
  29. ^ Southern Association of Forensic Scientists http://forendex.southernforensic.org/index.php/detail/index/602

External links[edit]