Methoxetamine

Systematic (IUPAC) name
(RS)2-(3-methoxyphenyl)-2-(ethylamino)cyclohexanone[1]
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	1239943-76-0 Y
ATC code	None
ChemSpider	24721792 Y
Chemical data
Formula	C15H21NO2
Mol. mass	247.33 g/mol
SMILES	eMolecules & PubChem
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
Y (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 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]

Physical properties[link]

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

Emergence[link]

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[link]

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]

Legal status[link]

Methoxetamine powder

• Prior to March 2012, MXE was not controlled by the UK's Misuse of Drugs Act.^[12] 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.^[13][14] The ACMD gave their advice on the March 23, 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."^[15] In April 2012, methoxetamine was placed under temporary class drug control, which prohibits its import and sale for 12 months.^[16]

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".^[17]

• MXE has been a controlled substance in Russia since October 2011^[18] and in Switzerland since December 2011.^[19]

Media coverage[link]

Mixmag reported in January 2012, that people in the dance music and clubbing community have given methoxetamine the slang name 'roflcoptr'.^[20] 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'.^[21] After being called mexxy in UK Home Office press releases users and the media adopted the name^[22] despite this being an uncommon term before its receiving media attention.^[23]

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."^[24]

See also[link]

• Dissociatives
• Phencyclidine
• Methoxydine
• Methoxyketamine

References[link]

External links[link]

Wikimedia Commons has media related to: Methoxetamine

• Erowid.org – Methoxetamine Information

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