Methoxetamine

Not to be confused with methoxamine.
Methoxetamine
Systematic (IUPAC) name
(R/S)-2-(3-Methoxyphenyl)-2-(ethylamino)cyclohexanone[1]
Clinical data
Legal status
Legal status
Pharmacokinetic data
Biological half-life 3-6 hours.
Identifiers
CAS Number 1239943-76-0 YesY
ATC code None
ChemSpider 24721792 YesY
Chemical data
Formula C15H21NO2
Molar mass 247.33 g/mol
  (verify)

Methoxetamine (MXE), or 3-MeO-2'-Oxo-PCE is a dissociative drug that has been sold as a designer drug.[1][2] Methoxetamine differs from many dissociatives such as ketamine and phencyclidine that were developed as pharmaceuticals in that it was designed for grey market distribution.[2][3]

Physical properties

Methoxetamine hydrochloride is soluble in ethanol up to 10 mg/ml at 25 °C.[4]

Pharmacology

Methoxetamine acts as a noncompetitive NMDA receptor antagonist and serotonin reuptake inhibitor.[5]

Emergence

The qualitative effects of methoxetamine were first described online in May 2010 and the compound became commercially available on a small scale in September 2010,[1][2] by November use and sale of the methoxetamine had increased enough for it to be formally identified by the European Monitoring Centre for Drugs and Drug Addiction. By July 2011, the EMCDDA had identified 58 websites selling the compound at a cost of 145–195 euros for 10 grams.[6] MXE remains popular despite bans in many countries.

Effects

Methoxetamine is reported to have a similar effect to ketamine,[7] with increased potency and duration.[8] Methoxetamine was often believed to possess opioid properties due to its structural similarity to 3-OH-PCP,[2] but this assumption is not supported by data, which shows insignificant affinity for the µ-opioid receptor by the compound itself, but metabolites which form in-vivo might have differing effects.[5] Recreational use of Methoxetamine has been associated with hospitalizations from high and/or combined consumption in the US and UK.[9][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.[10]

Methoxetamine was designed in part to prevent the urotoxicity associated with ketamine abuse; it was thought the compound's increased potency and reduced dose would limit the accumulation of urotoxic metabolites in the bladder.[2][3] Like ketamine, methoxetamine has been found to produce bladder inflammation and fibrosis after high dose, chronic administration in mice (although the dosages used were quite huge).[12] Reports of urotoxicity in humans have yet to appear in the medical literature.[2]

It is thought that methoxetamine may be an effective, fast-acting antidepressant like other NMDA antagonists with possibly even superior efficacy compared to ketamine. Its activity at other receptors may contribute to this.[13][8]

Legal status

Methoxetamine powder

Brazil

MXE became classified as a narcotic in Brazil in February 2014 .[14]

China

As of October 2015 MXE is a controlled substance in China.[15]

European Union

On 16 June 2014, the European Commission proposed that MXE be banned across the European Union, subjecting those in violation to criminal sanctions. This is following the procedure for risk-assessment and control of new psychoactive substances set up by the Council: Decision 2005/387/JHA.[16]

Poland

Methoxetamine is a controlled substance (group II-P) making it illegal to produce, sell or possess in The Republic of Poland as of 1 July 2015.[17]

Sweden

MXE became classified as a narcotic in Sweden in late February 2012.[18]

Japan

MXE became a controlled substance in Japan from 1 July 2012, by amendment to the Pharmaceutical Affairs Law.[19]

Russia

MXE has been a controlled substance in Russia since October 2011.[20]

Switzerland

MXE has been illegal in Switzerland since December 2011.[21]

Israel

MXE became classified as an illegal narcotic in Israel on May 2012 .[22][23]

United Kingdom

Prior to March 2012, MXE was not controlled by the UK's Misuse of Drugs Act.[24] In March 2012, the Home Office referred MXE to the Advisory Council on the Misuse of Drugs for possible temporary controlling under the powers given in the Police Reform and Social Responsibility Act 2011.[25][26] The ACMD gave their advice on 23 March, with the chair commenting that "the evidence shows that the use of methoxetamine can cause harm to users and the ACMD advises that it should be subject to a temporary class drug order."[27] In April 2012, methoxetamine was placed under temporary class drug control, which prohibits its import and sale for 12 months.[28]

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".[29]
On 18 October 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.[30]

United States

MXE is not scheduled at the federal level in the United States,[31] but it is possible that it could be considered an analog of PCE, in which case purchase, sales, or possession could be prosecuted under the Federal Analog Act. In September 2015, a bill was introduced into Congress that sought to make MXE a Schedule I substance.[32]

Alabama

Methoxetamine is a Schedule I controlled substance in the state of Alabama making it illegal to buy, sell, or possess in Alabama.[33]

Florida

Methoxetamine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[34]

Media coverage

Mixmag reported in January 2012, that people in the dance music and clubbing community have given methoxetamine the slang name 'roflcoptr'.[35] 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'.[36] After being called mexxy in UK Home Office press releases, the media adopted the name.[11][37]

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."[38]

Detection

A forensic standard of Methoxetamine is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[39]

See also

References

  1. 1 2 3 EMCDDA Annual Report 2010 (PDF) (Report). European Monitoring Centre for Drugs and Drug Addiction. 2010. Retrieved 2012-01-23.
  2. 1 2 3 4 5 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: 614–632. doi:10.1002/dta.1620. PMID 24678061.
  3. 1 2 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. ↑ https://www.caymanchem.com/msdss/11139m.pdf
  5. 1 2 "ACMD Methoxetamine Report (2012)". Advisory Council on the Misuse of Drugs. October 2012. pp. 14–15. Retrieved 6 February 2013.
  6. ↑ 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. 2011-11-15. Retrieved 2012-01-23.
  7. ↑ 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.
  8. 1 2 Coppola, M.; Mondola, R. (2012). "Methoxetamine: From drug of abuse to rapid-acting antidepressant". Medical Hypotheses 79: 504–7. doi:10.1016/j.mehy.2012.07.002. PMID 22819129.
  9. ↑ 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.
  10. 1 2 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.
  11. 1 2 "Pair hospitalised after taking designer drug mexxy". BBC News. 7 April 2014.
  12. ↑ Dargan, P.; Tang, H. (2014). "Three months of methoxetamine administration is associated with significant bladder and renal toxicity in mice". Clinical Toxicology 52: 176–180. doi:10.3109/15563650.2014.892605.
  13. ↑ Coppola, M.; Mondola, R. (2012-10-01). "Methoxetamine: from drug of abuse to rapid-acting antidepressant". Medical Hypotheses 79 (4): 504–507. doi:10.1016/j.mehy.2012.07.002. ISSN 1532-2777. PMID 22819129.
  14. ↑ "Anvisa inclui 21 substâncias em lista de drogas proibidas" (in Portuguese). Retrieved 2014-07-17.
  15. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
  16. ↑ "Legal highs: European Commission takes strong action with EU-wide ban on four new substances". Midday Express. European Commission. 16 June 2014. Retrieved 19 August 2014.
  17. ↑
  18. ↑ "Narkotika-klassning av sex nya substanser" (in Swedish). Retrieved 2013-11-26.
  19. ↑ 薬事法指定薬物　東京都福祉保健局 (in Japanese). Retrieved 2012-06-25.
  20. ↑ "Resolution of the Government of the Russian Federation on October 6, 2011 N 822" (in Russian). Retrieved 2012-02-20.
  21. ↑ "Ordinance on the lists of narcotic drugs, psychotropic substances, precursors and auxiliary chemicals" (in German). Retrieved 2012-02-20.
  22. ↑ "פקודת הסמים המסוכנים [נוסח חדש], תשל"ג-1973" (in Hebrew). Retrieved 2015-02-24.
  23. ↑ "הודעת הסמים המסוכנים (שינוי התוספת הראשונה לפקודה) (מס 2), התשע"ב-2012" (in Hebrew). Retrieved 2015-02-24.
  24. ↑ McPherson, P. (2012-02-13). "Health alert over drug sold as 'safe ketamine'". London: The Independent. Retrieved 2012-02-18.
  25. ↑ http://www.homeoffice.gov.uk/media-centre/news/mexxy
  26. ↑ Johnson, Wesley (2012-03-06). "Bid to ban 'safe' drug Methoxetamine after deaths". The Independent (London). Retrieved 2012-05-12.
  27. ↑ "Statement of evidence - methoxetamine" (PDF). UK Home Office. 2012-02-23. Retrieved 2012-03-29.
  28. ↑ "Methoxetamine". Home Office UK. Retrieved 2012-05-17.
  29. ↑ "Home Secretary's response to the ACMD's advice on methoxetamine". UK Home Office. 2012-03-28. Retrieved 2012-03-28.
  30. ↑ "Home Office circular 004-2013". UK Home Office. 2013-02-20. Retrieved 2013-02-27.
  31. ↑ §1308.11 Schedule I.
  32. ↑ "H.R. 3537: Synthetic Drug Control Act of 2015". GovTrack. 17 September 2015. Retrieved 18 February 2016.
  33. ↑
  34. ↑ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
  35. ↑ 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.
  36. ↑ Miller, A. (2011-02-11). "We Interviewed the Inventor of Roflcoptr, the New Drug Britain's Panicking About". Vice Magazine. Retrieved 2011-02-11.
  37. ↑ "Legal high drug 'mexxy' banned under new government powers". The Guardian (London). 28 March 2012.
  38. ↑ 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.
  39. ↑ Southern Association of Forensic Scientists http://forendex.southernforensic.org/index.php/detail/index/602

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