Methoxphenidine

Methoxphenidine
Systematic (IUPAC) name
(±)-1-[1-(2-methoxyphenyl)-2-phenylethyl]piperidine
Clinical data
Oral, Rectal
Identifiers
127529-46-8 Yes
PubChem CID 67833251
Chemical data
Formula C20H25NO
295.4186 g/mol

Methoxphenidine (methoxyphenidine, MXP, 2-MXP, 2-MeO-Diphenidine) is a dissociative drug that has been sold online as a research chemical.[1] Methoxphenidine was first reported in a 1989 patent where it was tested as a treatment for neurotoxic injury.[2] 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.[3] 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,[2] a structure–activity relationship shared by the anisylcyclohexylamines.

Acute methoxphenidine intoxication has been reported to produce confusion, hypertension, and tachycardia that was responsive to treatment with intravenous lorazepam,[4] methoxphenidine has also been associated with three published fatalities.[5]

See also

References

  1. ↑ 1.0 1.1 Morris, H.; Wallach, J. (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis 6: 614–632. doi:10.1002/dta.1620.
  2. ↑ 2.0 2.1 EP patent 0346791, Gray NM, Cheng BK, "1,2-diarylethylamines for treatment of neurotoxic injury", assigned to G.D. Searle & Co.
  3. ↑ McLaughlin, G.; Morris, N.; Kavanagh, P.; Power, J.; O'Brien, J.; Talbot, B.; Elliott, S.; Wallach, J.; Hoang, K.; Morris, H.; Brandt, S. (2015). "Test purchase, synthesis, and characterization of 2-methoxydiphenidine (MXP) and differentiation from its meta- and para-substituted isomers". Drug Testing and Analysis. doi:10.1002/dta.1800.
  4. ↑ Hofer, K.E.; Degrandi, C.; Müller, D.M.; Zürrer-Härdi, U.; Wahl, S.; Rauber-Lüthy, C.; Ceschi, A. (2014). "Acute toxicity associated with the recreational use of the novel dissociative psychoactive substance methoxphenidine". Clinical Toxicology 52: 1288–1291. doi:10.3109/15563650.2014.974264.
  5. ↑ Elliott, S.P.; Brandt, S.D.; Wallach, J.; Morris, H.; Kavanagh, S. (2015). "First Reported Fatalities Associated with the ‘Research Chemical’ 2-Methoxydiphenidine". Analytical Toxicology.