Methoxphenidine

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]

Methoxphenidine
Clinical data
Routes of
administration		Oral, Rectal
Legal status
Legal status
Identifiers
IUPAC name
  • (±)-1-[1-(2-methoxyphenyl)-2-phenylethyl]piperidine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC20H25NO
Molar mass295.426 g·mol−1
3D model (JSmol)
SMILES
  • COC1=C(C=CC=C1)C(CC2=CC=CC=C2)N3CCCCC3
InChI
  • InChI=1S/C20H25NO/c1-22-20-13-7-6-12-18(20)19(21-14-8-3-9-15-21)16-17-10-4-2-5-11-17/h2,4-7,10-13,19H,3,8-9,14-16H2,1H3
  • Key:QXXCUXIRBHSITD-UHFFFAOYSA-N

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]

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.[14] 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

References
  1. 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): 614–32. doi:10.1002/dta.1620. PMID 24678061.
  2. Van Hout MC, Hearne E (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. S2CID 6204908.
  3. Nancy M. Gray; Brian K. Cheng. "Patent EP 0346791 B1 - 1,2-diarylethylamines for treatment of neurotoxic injury". Archived from the original on 18 June 2015. Retrieved 17 June 2015.
  4. McLaughlin G, Morris N, Kavanagh PV, Power JD, O'Brien J, Talbot B, et al. (January 2016). "Test purchase, synthesis, and characterization of 2-methoxydiphenidine (MXP) and differentiation from its meta- and para-substituted isomers" (PDF). Drug Testing and Analysis. 8 (1): 98–109. doi:10.1002/dta.1800. PMID 25873326. Archived (PDF) from the original on 2020-03-09. Retrieved 2021-05-31.
  5. Sahai MA, Davidson C, Dutta N, Opacka-Juffry J (April 2018). "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. doi:10.3390/brainsci8040063. PMC 5924399. PMID 29642450.
  6. Wallach J, Kang H, Colestock T, Morris H, Bortolotto ZA, Collingridge GL, et al. (June 2016). "Pharmacological Investigations of the Dissociative 'Legal Highs' Diphenidine, Methoxphenidine and Analogues". PLOS ONE. 11 (6): e0157021. Bibcode:2016PLoSO..1157021W. doi:10.1371/journal.pone.0157021. PMC 4912077. PMID 27314670.
  7. Hofer KE, Degrandi C, Müller DM, 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" (PDF). Clinical Toxicology. 52 (10): 1288–91. doi:10.3109/15563650.2014.974264. PMID 25350467. S2CID 8513947. Archived (PDF) from the original on 2021-05-31. Retrieved 2021-05-31.
  8. Helander A, Beck O, Bäckberg M (June 2015). "Intoxications by the dissociative new psychoactive substances diphenidine and methoxphenidine". Clinical Toxicology. 53 (5): 446–53. doi:10.3109/15563650.2015.1033630. PMID 25881797. S2CID 5962038.
  9. Elliott SP, Brandt SD, Wallach J, Morris H, Kavanagh PV (May 2015). "First reported fatalities associated with the 'research chemical' 2-methoxydiphenidine". Journal of Analytical Toxicology. 39 (4): 287–93. doi:10.1093/jat/bkv006. PMID 25698777.
  10. Stachel N, Jacobsen-Bauer A, Skopp G (March 2016). "A methoxydiphenidine-impaired driver". International Journal of Legal Medicine. 130 (2): 405–9. doi:10.1007/s00414-015-1280-5. PMID 26482953. S2CID 6483817.
  11. "Man who killed mother believing her to be a witch sentenced to minimum of five years in jail". BBC News. 17 June 2016. Archived from the original on 24 August 2020. Retrieved 31 May 2021.
  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. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  13. "Fler ämnen föreslås bli klassade som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 24 March 2015. Archived from the original on 24 September 2015. Retrieved 21 October 2015.
  14. Arsenault D (1 June 2016). "Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18)". Canada Gazette. 150 (11). Archived from the original on 2017-12-02. Retrieved 2021-05-31.
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