Chemistry:Methoxphenidine

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Short description: Chemical compound
Methoxphenidine
Methoxphenidine structure.svg
Clinical data
Routes of
administration		Oral, Rectal
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC20H25NO
Molar mass295.426 g·mol−1
3D model (JSmol)

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][5] a structure–activity relationship shared by the arylcyclohexylamines.[6]

Side effects

Acute methoxphenidine intoxication has been reported to produce confusion, hypertension, and tachycardia that was responsive to treatment with intravenous lorazepam,[7][8] methoxphenidine has also been associated with three published fatalities[9] and one case of impaired driving.[10]

Psychotic episodes have also been reported, including a murder in June 2014.[11]

Legal status

As of October 2015 MXP is a controlled substance in China.[12]

MXP is also banned in Sweden.[13]

In Canada, MT-45 and its analogues were made Schedule I controlled substances, which includes DPD in its structural group.[14] Possession without legal authority can result in maximum seven years imprisonment. Further, Health Canada amended the Food and Drug Regulations in May, 2016 to classify explicitly DPD 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

References

  1. ↑ 1.0 1.1 "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis 6 (7–8): 614–632. July–August 2014. doi:10.1002/dta.1620. PMID 24678061. 
  2. ↑ ""Word of mouse": indigenous harm reduction and online consumerism of the synthetic compound methoxphenidine". Journal of Psychoactive Drugs 47 (1): 30–41. January–March 2015. doi:10.1080/02791072.2014.974002. PMID 25715070. 
  3. ↑ 3.0 3.1 Gray NM, Cheng BK, "1,2-diarylethylamines for treatment of neurotoxic injury", EP patent 0346791, issued 6 April 1994
  4. ↑ "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. January 2016. doi:10.1002/dta.1800. PMID 25873326. http://researchonline.ljmu.ac.uk/id/eprint/3276/1/DTA-15-0028.R1.pdf. Retrieved 2021-05-31. 
  5. ↑ "Mechanistic Insights into the Stimulant Properties of Novel Psychoactive Substances (NPS) and Their Discrimination by the Dopamine Transporter-In Silico and In Vitro Exploration of Dissociative Diarylethylamines". Brain Sciences 8 (4): 63. April 2018. doi:10.3390/brainsci8040063. PMID 29642450. 
  6. ↑ "Pharmacological Investigations of the Dissociative 'Legal Highs' Diphenidine, Methoxphenidine and Analogues". PLOS ONE 11 (6): e0157021. June 2016. doi:10.1371/journal.pone.0157021. PMID 27314670. Bibcode: 2016PLoSO..1157021W. 
  7. ↑ "Acute toxicity associated with the recreational use of the novel dissociative psychoactive substance methoxphenidine". Clinical Toxicology 52 (10): 1288–1291. December 2014. doi:10.3109/15563650.2014.974264. PMID 25350467. http://www.zora.uzh.ch/id/eprint/100067/1/Revision_complete%2520text_clean_LCLT-2014-0299_Methoxphenidine_not%2520for%2520review.pdf. Retrieved 2021-05-31. 
  8. ↑ "Intoxications by the dissociative new psychoactive substances diphenidine and methoxphenidine". Clinical Toxicology 53 (5): 446–453. June 2015. doi:10.3109/15563650.2015.1033630. PMID 25881797. 
  9. ↑ "First reported fatalities associated with the 'research chemical' 2-methoxydiphenidine". Journal of Analytical Toxicology 39 (4): 287–293. May 2015. doi:10.1093/jat/bkv006. PMID 25698777. 
  10. ↑ "A methoxydiphenidine-impaired driver". International Journal of Legal Medicine 130 (2): 405–409. March 2016. doi:10.1007/s00414-015-1280-5. PMID 26482953. 
  11. ↑ "Man who killed mother believing her to be a witch sentenced to minimum of five years in jail". BBC News. 17 June 2016. https://www.bbc.com/news/uk-northern-ireland-36556909. 
  12. ↑ "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. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  13. ↑ "Fler ämnen föreslås bli klassade som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 24 March 2015. http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/mars/fler-amnen-foreslas-bli-klassade-som-narkotika-eller-halsofarlig-vara/. 
  14. ↑ "Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18)". Canada Gazette 150 (11). 1 June 2016. http://www.gazette.gc.ca/rp-pr/p2/2016/2016-06-01/html/sor-dors106-eng.php. Retrieved 2016-11-17. 



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