Methoxphenidine

Methoxphenidine
Clinical data
Routes of
administration		Oral, Rectal
Legal status
Legal status
Identifiers
  • (±)-1-[1-(2-methoxyphenyl)-2-phenylethyl]piperidine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H25NO
Molar mass295.426 g·mol−1
3D model (JSmol)
  • COC1=C(C=CC=C1)C(CC2=CC=CC=C2)N3CCCCC3
  • 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

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]

  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. ^ 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. ^ a b EP 0346791, Gray NM, Cheng BK, "1,2-diarylethylamines for treatment of neurotoxic injury", issued 6 April 1994, assigned to GD Searle LLC 
  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. S2CID 33626099. 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.