Methoxphenidine

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Methoxphenidine
Methoxphenidine structure.svg
Clinical data
Routes of
administration		 Oral, Rectal
Legal status
Legal status
  • Illegal in China and Sweden
Identifiers
CAS Number 127529-46-8 YesY
PubChem (CID) 67833251
ChemSpider 52085156
UNII H2W7A6GZGX
Chemical and physical data
Formula C20H25NO
Molar mass 295.4186 g/mol
3D model (Jmol) Interactive image

Methoxphenidine (methoxydiphenidine, 2-MeO-Diphenidine, MXP) is a dissociative of the diarylethylamine class that has been sold online as a designer drug.[1][2] Methoxphenidine was first reported in a 1989 patent where it was tested as a treatment for neurotoxic injury.[3] 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.[4] Though diphenidine possesses higher affinity for the NMDA receptor, anecdotal reports suggest methoxphenidine has greater oral potency.[1] 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,[3] a structure–activity relationship shared by the arylcyclohexylamines.[5]

Side effects[edit]

Acute methoxphenidine intoxication has been reported to produce confusion, hypertension, and tachycardia that was responsive to treatment with intravenous lorazepam,[6][7] methoxphenidine has also been associated with three published fatalities[8] and one case of impaired driving.[9]

Psychotic episodes have also been reported, including a murder in June 2014.[10]

Legal Status[edit]

As of October 2015 MXP is a controlled substance in China.[11]

MXP is also banned in Sweden.[12]

In Canada, MT-45 and its analogues were made Schedule I controlled substances.[13] Possession without legal authority can result in maximum 7 years imprisonment. Further, Health Canada amended the Food and Drug Regulations in May, 2016 to classify MXP as a restricted drug. Only those with a law enforcement agency, person with an exemption permit or institutions with Minister's authorization may possess the drug.

See also[edit]

References[edit]

  1. ^ a b Morris, H.; Wallach, J. (July–August 2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7-8): 614–632. doi:10.1002/dta.1620. PMID 24678061. 
  2. ^ Marie Claire Van Hout; Evelyn Hearne (January–March 2015). ""Word of Mouse": Indigenous Harm Reduction and Online Consumerism of the Synthetic Compound Methoxphenidine". Journal of Psychoactive Drugs. 47 (1): 30–41. doi:10.1080/02791072.2014.974002. PMID 25715070. 
  3. ^ a b Nancy M. Gray; Brian K. Cheng. "Patent EP 0346791 B1 - 1,2-diarylethylamines for treatment of neurotoxic injury". Retrieved 17 June 2015. 
  4. ^ McLaughlin, G.; Morris, N.; Kavanagh, P.; Power, J.; O'Brien, J.; Talbot, B.; Elliott, S.; Wallach, J.; Hoang, K.; Morris, H.; Brandt, S. (January 2016). "Test purchase, synthesis, and characterization of 2-methoxydiphenidine (MXP) and differentiation from its meta- and para-substituted isomers". Drug Testing and Analysis. 8 (1): 98–109. doi:10.1002/dta.1800. PMID 25873326. 
  5. ^ Jason Wallach; Heather Kang; Tristan Colestock; Hamilton Morris; Zuner A. Bortolotto; Graham L. Collingridge; David Lodge; Adam L. Halberstadt; Simon D. Brandt; Adeboye Adejare (June 2016). "Pharmacological Investigations of the Dissociative 'Legal Highs' Diphenidine, Methoxphenidine and Analogues". PLOS ONE. 11 (6): e0157021. doi:10.1371/journal.pone.0157021. PMC 4912077Freely accessible. PMID 27314670. 
  6. ^ Hofer, K.E.; Degrandi, C.; Müller, D.M.; Zürrer-Härdi, U.; Wahl, S.; Rauber-Lüthy, C.; Ceschi, A. (December 2014). "Acute toxicity associated with the recreational use of the novel dissociative psychoactive substance methoxphenidine". Clinical Toxicology. 52 (10): 1288–1291. doi:10.3109/15563650.2014.974264. PMID 25350467. 
  7. ^ Anders Helander; Olof Beck; Matilda Bäckberg (June 2015). "Intoxications by the dissociative new psychoactive substances diphenidine and methoxphenidine". Clinical Toxicology. 53 (5): 446–453. doi:10.3109/15563650.2015.1033630. PMID 25881797. 
  8. ^ Simon P. Elliott1; Simon D. Brandt; Jason Wallach; Hamilton Morris; Pierce V. Kavanagh (May 2015). "First Reported Fatalities Associated with the 'Research Chemical' 2-Methoxydiphenidine". Analytical Toxicology. 39 (4): 287–293. doi:10.1093/jat/bkv006. PMID 25698777. 
  9. ^ Nicole Stachel; Andrea Jacobsen-Bauer; Gisela Skopp (March 2016). "A methoxydiphenidine-impaired driver". International Journal of Legal Medicine. 130 (2): 405–409. doi:10.1007/s00414-015-1280-5. PMID 26482953. 
  10. ^ "Man who killed mother believing her to be a witch sentenced to minimum of five years in jail". BBC News. 17 June 2016. 
  11. ^ "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. 
  12. ^ "Fler ämnen föreslås bli klassade som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 24 March 2015. Retrieved 21 October 2015. 
  13. ^ Denis Arsenault (1 June 2016). "Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18)". Canada Gazette. Government of Canada. 150 (11). 


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