Methoxetamine

Last updated

Methoxetamine
Methoxetamine2DCSD.svg
MXE.png
Clinical data
Other namesMXE; 3-MeO-2'-oxo-PCE
Addiction
liability 		High [1]
Drug class NMDA receptor antagonists; Dissociative hallucinogens; General anesthetics
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 3–6 hours
Identifiers
  • (R/S)-2-(3-Methoxyphenyl)-2-(ethylamino)cyclohexanone [5]
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H21NO2
Molar mass 247.338 g·mol−1
3D model (JSmol)
  • O=C1CCCCC1(C2=CC=CC(OC)=C2)NCC
  • 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 Yes check.svgY
  • Key:LPKTWLVEGBNOOX-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Methoxetamine, abbreviated as MXE, is a dissociative hallucinogen that has been sold as a designer drug. [5] [6] It differs from many dissociatives such as ketamine and phencyclidine (PCP) that were developed as pharmaceutical drugs for use as general anesthetics in that it was designed specifically to increase the antidepressant effects of ketamine. [6] [7]

Contents

MXE is an arylcyclohexylamine. [8] It acts mainly as an NMDA receptor antagonist, similarly to other arylcyclohexylamines like ketamine and PCP. [8]

Recreational use

Effects

Methoxetamine powder. Methoxetamine-2.JPG
Methoxetamine powder.

MXE is reported to have a similar effect to ketamine. [1] It was often believed to possess opioid properties due to its structural similarity to 3-HO-PCP, [6] but this assumption is not supported by data, which shows insignificant affinity for the μ-opioid receptor by the compound. [8] Recreational use of MXE 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 MXE overdose, lasting for between one and four days after exposure. [10]

MXE was designed in part in an attempt to avoid 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. [6] [7] Like ketamine, MXE has been found to produce bladder inflammation and fibrosis after high dose chronic administration in mice, although the dosages used were quite large. [12] Reports of urotoxicity in humans have yet to appear in the medical literature. [6]

Pharmacology

Pharmacodynamics

Methoxetamine [13] [8]
SiteKi (nM)ActionSpeciesRef
NMDA
(PCP) 		259AntagonistHuman [8]
MOR Tooltip μ-Opioid receptor>10,000NDHuman [8]
DOR Tooltip δ-Opioid receptor>10,000NDHuman [8]
KOR Tooltip κ-Opioid receptor>10,000NDHuman [8]
NOP Tooltip Nociceptin receptor>10,000NDHuman [8]
σ1 >10,000NDGuinea pig [8]
σ2 >10,000NDRat [8]
D2 >10,000NDHuman [8]
5-HT2A >10,000NDHuman [8]
SERT Tooltip Serotonin transporter481
2,400 (IC50)		InhibitorHuman [8]
[14]
NET Tooltip Norepinephrine transporter>10,000
20,000 (IC50)		InhibitorHuman [8]
[14]
DAT Tooltip Dopamine transporter>10,000
33,000 (IC50)		InhibitorHuman [8]
[14]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

MXE acts mainly as a selective and high-affinity NMDA receptor antagonist, specifically of the dizocilpine (MK-801) site (Ki = 257 nM). [8] [15] It produces ketamine-like effects. [15] [16] In addition to antagonism of the NMDA receptor, MXE has been found to act as a serotonin reuptake inhibitor (Ki = 479 nM; IC50 = 2,400 nM). [8] [14] Conversely, it shows little or no effect on the reuptake of dopamine and norepinephrine (Ki and IC50 > 10,000 nM). [8] [14] Nonetheless, MXE has been found to activate dopaminergic neurotransmission, including in the mesolimbic reward pathway. [15] This is a characteristic that it shares with other NMDA receptor antagonists, including ketamine, PCP, and dizocilpine (MK-801). [15] Animal studies suggest MXE may have rapidly-acting antidepressant effects similar to those of ketamine. [15] [17] A study that assessed binding of MXE at 56 sites including neurotransmitter receptors and transporters found that MXE had Ki values of >10,000 nM for all sites except the dizocilpine site of the NMDA receptor and the serotonin transporter (SERT). [8]

Pharmacokinetics

MXE has a longer duration of action than that of ketamine. [18]

Chemistry

Methoxetamine and related arylcyclohexylamines. Arylcyclohexylamines.png
Methoxetamine and related arylcyclohexylamines.

MXE is an arylcyclohexylamine and a derivative of eticyclidine (PCE). It can also be thought of as the β-Keto-derivative of 3-methoxyeticyclidine (3-MeO-PCE), or the N-ethyl homologue of methoxmetamine (MXM) and methoxpropamine (MXPr). It is closely related structurally to ketamine, and more distantly to PCP.

MXE hydrochloride is soluble in ethanol up to 10 mg/ml at 25 °C. [19]

Detection in body fluids

A forensic standard of MXE is available, and the compound has been posted on the Forendex website of potential drugs of abuse. [20]

History

The qualitative effects of MXE were first described online in May 2010 and the compound became commercially available on a small scale in September 2010. [5] [6] By November the use and sale of the MXE 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. [21]

Society and culture

Methoxetamine powder. Methoxetamine-3.jpg
Methoxetamine powder.

Media coverage

Mixmag reported in January 2012, that people in the dance music and clubbing community have given MXE 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] After being called mexxy in UK Home Office press releases, the media adopted the name. [11] [24]

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 MXE, may constitute a pressing public health challenge. Better international collaboration levels and novel forms of intervention are necessary to tackle this fast-growing phenomenon." [25]

Brazil

MXE became classified as a narcotic in Brazil in February 2014. [26]

Canada

As of January 2010 MXE is a controlled substance in Canada. [27]

China

As of October 2015 MXE is a controlled substance in China. [28]

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. [29]

Finland

Scheduled in "government decree on narcotic substances, preparations and plants" and is hence illegal. [30]

Israel

MXE became classified as an illegal narcotic in Israel in May 2012. [31] [32]

Japan

MXE became a controlled substance in Japan from 1 July 2012, by amendment to the Pharmaceutical Affairs Law. [33] [34]

Poland

MXE 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. [35]

Russia

MXE has been a controlled substance in Russia since October 2011. [36]

Sweden

MXE became classified as a narcotic in Sweden in late February 2012. [37]

Switzerland

MXE has been illegal in Switzerland since December 2011. [38]

United Kingdom

Prior to March 2012, MXE was not controlled by the UK's Misuse of Drugs Act. [39] 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. [40] [41] 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." [42] In April 2012, MXE was placed under temporary class drug control, which prohibited its import and sale for 12 months. [43]

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 MXE 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". [44]

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. [45]

United Nations

MXE was made a schedule II drug in November 2016. [46]

United States

On June 6, 2022, the U.S. Drug Enforcement Administration published a final rule placing MXE in Schedule I of the Controlled Substances Act. [47]

Alabama
MXE is a Schedule I controlled substance in the state of Alabama making it illegal to buy, sell, or possess in Alabama. [48]
Florida
MXE is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida. [49]
Utah
MXE is a controlled substance in the state of Utah making it illegal to buy, sell, or possess in Utah. [50]

Related Research Articles

<span class="mw-page-title-main">Phencyclidine</span> Dissociative hallucinogenic drug, mostly used recreationally

Phencyclidine or phenylcyclohexyl piperidine (PCP), also known in its use as a street drug as angel dust among other names, is a dissociative anesthetic mainly used recreationally for its significant mind-altering effects. PCP may cause hallucinations, distorted perceptions of sounds, and violent behavior. As a recreational drug, it is typically smoked, but may be taken by mouth, snorted, or injected. It may also be mixed with cannabis or tobacco.

<span class="mw-page-title-main">NMDA receptor antagonist</span> Class of anesthetics

NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the N-Methyl-D-aspartate receptor (NMDAR). They are commonly used as anesthetics for humans and animals; the state of anesthesia they induce is referred to as dissociative anesthesia.

<span class="mw-page-title-main">Eticyclidine</span> Medication

Eticyclidine is a dissociative anesthetic drug with hallucinogenic effects. It is similar in effects to phencyclidine but is slightly more potent. PCE was developed by Parke-Davis in the 1970s and evaluated for anesthetic potential under the code name CI-400, but research into PCE was not continued after the development of ketamine, a similar drug with more favourable properties. Due to its similarity in effects to PCP, PCE was placed into the Schedule 1 list of illegal drugs in the 1970s, although it was only briefly abused in the 1970s and 1980s and is now little known.

<span class="mw-page-title-main">Tenocyclidine</span> Chemical compound

Tenocyclidine (TCP) is a dissociative anesthetic with psychostimulant effects. It was discovered by a team at Parke-Davis in the late 1950s. It is similar in effects to phencyclidine (PCP) but is considerably more potent. TCP has slightly different binding properties to PCP, with more affinity for the NMDA receptors, but less affinity for the sigma receptors. Because of its high affinity for the PCP site of the NMDA receptor complex, the 3H radiolabelled form of TCP is widely used in research into NMDA receptors.

Gacyclidine is a psychoactive drug which acts as a dissociative via functioning as a non-competitive NMDA receptor antagonist. It is closely related to phencyclidine (PCP), and specifically, is a derivative of tenocyclidine (TCP).

<span class="mw-page-title-main">Benocyclidine</span> Chemical compound

Benocyclidine, also known as benzo​thiophenyl​cyclo​hexylpiperidine (BTCP), is a psychoactive recreational drug of the arylcyclohexylamine class which is related to phencyclidine (PCP). It was first described in a patent application naming Marc Caron and colleagues at Duke University in 1997.

<span class="mw-page-title-main">Arylcyclohexylamine</span> Class of chemical compounds

Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.

<span class="mw-page-title-main">3-MeO-PCP</span> Chemical compound

3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative hallucinogen of the arylcyclohexylamine class related to phencyclidine (PCP) which has been sold online as a designer drug. It has been used across Europe and the United States. In some cases, consumption has been known to be fatal. It acts mainly as an NMDA receptor antagonist, though it has also been found to interact with the sigma σ1 receptor and the serotonin transporter. The drug does not possess any opioid activity nor does it act as a dopamine reuptake inhibitor.

<span class="mw-page-title-main">4-MeO-PCP</span> Chemical compound

4-Methoxyphencyclidine is a dissociative anesthetic drug that has been sold online as a research chemical. The synthesis of 4-MeO-PCP was first reported in 1965 by the Parke-Davis medicinal chemist Victor Maddox. A 1999 review published by a chemist using the pseudonym John Q. Beagle suggested the potency of 4-MeO-PCP in man was reduced relative to PCP, two years later Beagle published a detailed description of the synthesis and qualitative effects of 4-MeO-PCP, which he said possessed 70% the potency of PCP. 4-MeO-PCP was the first arylcyclohexylamine research chemical to be sold online, it was introduced in late 2008 by a company trading under the name CBAY and was followed by several related compounds such as 3-MeO-PCP and methoxetamine. 4-MeO-PCP has lower affinity for the NMDA receptor than PCP, but higher affinity than ketamine, it is orally active in a dosage range similar to ketamine, with some users requiring doses in excess of 100 mg for desired effects. Users have reported substantial differences in active dose, these discrepancies can be partially explained by the presence of unreacted PCC and other impurities in samples sold on the grey market. 4-MeO-PCP has Ki values of 404 nM for the NMDA receptor, 713 nM for the norepinephrine transporter, 844 nM for the serotonin transporter, 296 nM for the σ1 receptor and 143 nM for the σ2 receptor.

A temporary class drug is a relatively new status for controlled drugs, which has been adopted in some jurisdictions, notably New Zealand and the United Kingdom, to attempt to bring newly synthesised designer drugs under legal control. The controlled drug legislation in these jurisdictions requires drug scheduling decisions to follow an evidence-based process, where the harms of the drug are assessed and reviewed so that an appropriate legal status can be assigned. Since many designer drugs sold in recent years have had little or no published research that could help inform such a decision, they have been widely sold as "legal highs", often for months, before sufficient evidence accumulates to justify placing them on the controlled drug schedules.

<i>N</i>-Ethylnorketamine Chemical compound

N-Ethylnorketamine is a designer drug which is presumed to have similar properties to ketamine, a dissociative anesthetic drug with hallucinogenic and sedative effects. It has been sold over the internet since around September 2012, and identified in seized drug samples by analytical laboratories in the UK and other European countries.

<span class="mw-page-title-main">Diphenidine</span> Dissociative anesthetic designer drug

Diphenidine is a dissociative anesthetic that has been sold as a designer drug. The synthesis of diphenidine was first reported in 1924, and employed a Bruylants reaction analogous to the one that would later be used to discover phencyclidine in 1956. Shortly after the 2013 UK ban on arylcyclohexylamines, diphenidine and the related compound methoxphenidine became available on the grey market. Anecdotal reports describe high doses of diphenidine producing "bizarre somatosensory phenomena and transient anterograde amnesia." Diphenidine and related diarylethylamines have been studied in vitro as treatments for neurotoxic injury and are antagonists of the NMDA receptor. In dogs diphenidine exhibits greater antitussive potency than codeine phosphate.

<span class="mw-page-title-main">Methoxphenidine</span> Chemical compound

Methoxphenidine is a dissociative of the diarylethylamine class that has been sold online as a designer drug. Methoxphenidine was first reported in a 1989 patent where it was tested as a treatment for neurotoxic injury. Shortly after the 2013 UK ban on arylcyclohexylamines methoxphenidine and the related compound diphenidine became available on the gray market, where it has been encountered as a powder and in tablet form. Though diphenidine possesses higher affinity for the NMDA receptor, anecdotal reports suggest methoxphenidine has greater oral potency. Of the three isomeric anisyl-substituents methoxphenidine has affinity for the NMDA receptor that is higher than 4-MeO-diphenidine but lower than 3-MeO-diphenidine, a structure–activity relationship shared by the arylcyclohexylamines.

<span class="mw-page-title-main">Ephenidine</span> Dissociative anesthetic designer drug

Ephenidine is a dissociative anesthetic that has been sold online as a designer drug. It is illegal in some countries as a structural isomer of the banned opioid drug lefetamine, but has been sold in countries where it is not yet banned.

<span class="mw-page-title-main">3-MeO-PCE</span> Chemical compound

3-Methoxyeticyclidine (3-MeO-PCE), also known as methoxieticyclidine, is a dissociative anesthetic that is qualitatively similar to PCE and PCP and has been sold online as a designer drug.

<span class="mw-page-title-main">3-HO-PCP</span> Chemical compound

3-Hydroxyphencyclidine (3-HO-PCP) is a dissociative of the arylcyclohexylamine class related to phencyclidine (PCP) that has been sold online as a designer drug.

<span class="mw-page-title-main">2-Fluorodeschloroketamine</span> Chemical compound

2-Fluorodeschloroketamine is a dissociative anesthetic related to ketamine. Its sale and use as a designer drug has been reported in various countries. It is an analogue of ketamine where the chlorine group has been replaced by fluorine. Due to its recent emergence, the pharmacological specifics of the compound are mostly unclear, but effects are reported to be similar to its parent compound, ketamine.

<span class="mw-page-title-main">3-Methyl-PCPy</span> Chemical compound

3-Methyl-PCPy (3-Me-PCPy) is an arylcyclohexylamine derivative with an unusual spectrum of pharmacological effects, acting as both a potent NMDA antagonist and also a triple reuptake inhibitor which inhibits reuptake of all three monoamine neurotransmitters serotonin, dopamine and noradrenaline. It also acts as a high affinity sigma receptor ligand, selective for the σ2 subtype. It produces both stimulant and dissociative effects in animal behavioural studies.

<span class="mw-page-title-main">2-Oxo-PCE</span> Chemical compound

2-Oxo-PCE is a dissociative anesthetic of the arylcyclohexylamine class that is closely related to deschloroketamine and eticyclidine, and has been sold online as a designer drug.

<span class="mw-page-title-main">Hydroxetamine</span> Chemical compound

Hydroxetamine is a recreational designer drug from the arylcyclohexylamine family, with dissociative effects. It is known as an active metabolite of the dissociative designer drug methoxetamine, but has also been sold in its own right since late 2019.

References

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  41. ↑ Johnson W (6 March 2012). "Bid to ban 'safe' drug Methoxetamine after deaths". The Independent. London. Archived from the original on 13 May 2012. Retrieved 12 May 2012.
  42. ↑ "Statement of evidence - Methoxetamine". gov.uk. 27 February 2012. Archived from the original on 31 March 2012. Retrieved 28 January 2021.
  43. ↑ "Methoxetamine". UK Home Office. Archived from the original on 12 April 2012. Retrieved 17 May 2012.
  44. ↑ "Home Secretary's response to the ACMD's advice on methoxetamine". gov.uk. 27 March 2012. Archived from the original on 5 April 2012. Retrieved 28 January 2021.
  45. ↑ "Home Office circular 004-2013". gov.uk. 20 February 2013. Archived from the original on 5 March 2013. Retrieved 28 January 2021.
  46. ↑ "UNODC: Commission on Narcotic Drugs decision on international control of PMMA, α-PVP, 4,4'-DMAR, MXE and Phenazepam enters into force". 13 November 2016. Archived from the original on 8 November 2020.
  47. ↑ "Schedules of Controlled Substances: Placement of Methoxetamine (MXE) in Schedule I". Federal Register. 6 June 2022. Retrieved 6 June 2022.
  48. ↑ "Chapter 420-7-2 Controlled Substances" (PDF). Alabama State Board of Health. Archived (PDF) from the original on 10 March 2016. Retrieved 22 April 2015.
  49. ↑ "Statutes & Constitution :View Statutes : Online Sunshine". leg.state.fl.us. Archived from the original on 14 March 2018. Retrieved 7 May 2018.
  50. ↑ Utah Code 58-37-4.2. Listed controlled substances. Archived 24 April 2016 at the Wayback Machine
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