Methoxetamine

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Structural formula
Structure of methoxetamine
Structure without stereochemistry
General
Surname Methoxetamine
other names
  • MXE
  • 3-MeO-2'-Oxo-PCE
  • 2- (3-methoxyphenyl) -2- ( N -ethylamino) cyclohexanone ( IUPAC )
Molecular formula C 15 H 21 NO 2
Brief description

white solid (hydrochloride)

External identifiers / databases
CAS number
  • 1239943-76-0 (base)
  • 1239908-48-5 (hydrochloride)
PubChem 52911279
ChemSpider 24721792
Wikidata Q903303
properties
Molar mass 247.33 g mol −1 (base)
Physical state

firmly

Melting point

244.9 ° C (hydrochloride)

solubility
  • ~ 10 mg / ml in EtOH * ~ 5 mg / ml in DMF * ~ 14 mg / ml in DMSO
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Methoxetamine (MXE) or 3-MeO-2'-Oxo-PCE structurally belongs to the group of arylcyclohexylamines and is therefore a derivative of ketamine , which also has structural properties in common with eticyclidine and 3-MeO-PCP . It is assumed that methoxetamine acts as an NMDA receptor antagonist and dopamine reuptake inhibitor, but this has only been formally proven for the NMDA receptor effect. Methoxetamine differs from many other dissociative anesthetics in that it was specially developed for distribution in semi-legal markets.

Stereochemistry

Methoxetamine is a chiral compound that contains an asymmetrically substituted carbon atom. The compound is therefore usually a 1: 1 mixture ( racemate ) of two mirror-image molecules ( enantiomers ), which can differ in certain physical properties and physiological effects. The individual stereoisomers can be isolated in a targeted manner by suitable synthesis strategies (see also: enantiomerically pure drug synthesis ) or separation processes ( racemate resolution ). After the synthesis that follows, methoxetamine is obtained as a racemate.

synthesis

Methoxetamine synthesis.svg

The corresponding ketone is obtained by reacting 3-methoxybenzonitrile with cyclopentyl magnesium bromide . A tertiary bromide is formed with elemental bromine . This hydrolyzes in the presence of ethylamine and thereby receives both a hydroxyl group and the imine function. When heated, this compound is rearranged to methoxetamine.

effect

So far, a similar effect as that of the ketamine has been described by the similar binding to the NMDA glutamate receptor , such. B. dissociative experience, increased pulse ( tachycardia ) and increased blood pressure ( arterial hypertension ). However, due to the 3-methoxy substitution, the pain-relieving effect of MXE due to the binding to the µ1 opioid receptor is more pronounced than that of ketamine; in contrast to the dissociative effect, which is less pronounced. Furthermore, euphoria , empathy , hallucinations, dizziness, states of confusion, motor disorders and short-term memory loss are described as effects. In the absence of long-term studies, nothing is known about the toxicity of MXE, so misuse can lead to health problems.

Legal position

Methoxetamine crystals
  • Germany
In Germany, methoxetamine has been listed in Appendix I of the Narcotics Act since July 17, 2013 with the 27th Narcotics Amendment Ordinance and thus classified as a non-marketable substance.
  • European Union
On September 25, 2014, the EU banned methoxetamine, among other things. The manufacture and sale of the substance has therefore been prohibited since October 2, 2015.

Web links

literature

  • MT Zanda, P. Fadda, C. Chiamulera, W. Fratta, L. Fattore: Methoxetamine, a novel psychoactive substance with serious adverse pharmacological effects: a review of case reports and preclinical findings. In: Behavioral pharmacology. Volume 27, Number 6, September 2016, pp. 489-496, doi : 10.1097 / FBP.0000000000000241 , PMID 27128862 .
  • JB Zawilska: Methoxetamine - a novel recreational drug with potent hallucinogenic properties. In: Toxicology letters. Volume 230, number 3, November 2014, pp. 402-407, doi : 10.1016 / j.toxlet.2014.08.011 , PMID 25128700 (review).
  • A. Kjellgren, K. Jonsson: Methoxetamine (MXE) - a phenomenological study of experiences induced by a "legal high" from the internet. In: Journal of psychoactive drugs. Volume 45, number 3, 2013 Jul – Aug, pp. 276–286, doi : 10.1080 / 02791072.2013.803647 , PMID 24175493 , PMC 3756617 (free full text).
  • Jennifer E. Shields, Paul I. Dargan, David M. Wood, Malgorzata Puchnarewicz, Susannah Davies, W. Stephen Waring: Methoxetamine associated reversible cerebellar toxicity: Three cases with analytical confirmation. In: Clinical Toxicology . June 2012, Vol. 50, No. 5, 438-440, PMID 22578175 . doi: 10.3109 / 15563650.2012.683437
  • O. Corazza, F. Schifano, P. Simonato, S. Fergus, S. Assi et al: Phenomenon of new drugs on the Internet: the case of ketamine derivative methoxetamine. In: Hum Psychopharmacol. 27 (2), 2012 Mar, pp. 145-149. PMID 22389078 . doi: 10.1002 / hup.1242
  • J. Ward, S. Rhyee, J. Plansky, E. Boyer: Methoxetamine: a novel ketamine analog and growing health-care concern. In: Clin Toxicol (Phila). 49 (9), 2011 Nov, pp. 874-875. Epub 2011 Oct 7. PMID 21981756 .

Individual evidence

  1. ↑ a b SWGDRUG Monographs: Methoxetamine Monograph (PDF; 511 kB), accessed on May 20, 2013.
  2. ↑ a b c Cayman Chemical Company: Methoxetamine (hydrochloride) SAFETY DATA SHEET (PDF; 23 kB), accessed on May 19, 2013.
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ↑ Bryan L. Roth, Simon Gibbons, Warunya Arunotayanun, Xi-Ping Huang, Vincent Setola, Ric Treble, Les Iversen, Kenji Hashimoto: The Ketamine Analogue Methoxetamine and 3- and 4-Methoxy Analogues of Phencyclidine Are High Affinity and Selective Ligands for the Glutamate NMDA Receptor. In: PLoS ONE. 8, 2013, p. E59334, doi: 10.1371 / journal.pone.0059334 .
  5. ↑ a b Hamilton Morris: Interview with a ketamine chemist . In: Vice Magazine. Retrieved February 3, 2012.
  6. ↑ a b Patrick A. Hays, John F. Casale, Arthur L. Berrier (US Department of Justice Drug Enforcement Administration): The Characterization of 2- (3-Methoxyphenyl) -2- (ethylamino) cyclohexanone (Methoxetamine). (PDF; 1.9 MB) In: Microgram Journal. Volume 9, Number 1, 2012, pp. 3-17.
  7. ^ A b D. M. Wood, S. Davies, M. Puchnarewicz, A. Johnston, PI Dargan: Acute toxicity associated with the recreational use of the ketamine derivative methoxetamine . In: European Journal of Clinical Pharmacology . 2011, PMID 22205276 .
  8. ↑ DM Wood, S. Davies, A. Calapis, J. Ramsey, PI Dargan: Novel drugs -novel branding. In: QJM . 2011 Oct 13. PMID 21997441 . doi: 10.1093 / qjmed / hcr191
  9. ^ Federal Ministry of Health : Cabinet adopts 27th Narcotics Amendment Ordinance. Press release of May 22, 2013, accessed on May 26, 2013.
  10. ↑ Federal Ministry of Health : Draft ordinance of the federal government: Twenty-seventh ordinance amending the provisions of the law on narcotics (PDF; 73kb). ( Memento of the original from February 21, 2014 in the Internet Archive ) Info: The @1@ 2Template: Webachiv / IABot / www.bmg.bund.de archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. Retrieved July 17, 2013.
  11. ↑ a b Implementing decision of the Council of September 25, 2014 (2014/688 / EU) (PDF) accessed on October 17, 2014.
  12. ↑ EU bans four dangerous designer drugs. on: aerzteblatt.de , September 26, 2014, accessed on October 17, 2014.
  13. ↑ MDPV, 25I-NBOMe, AH-7921 and methoxetamine: EU bans four novel drugs. on: rp-online.de , September 25, 2014, accessed on October 17, 2014.