Diphenidine

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Diphenidine
Diphenidine.svg
Systematic (IUPAC) name
(±)-1-(1,2-Diphenylethyl)piperidine
Clinical data
Legal status
?
Identifiers
CAS number 36794-52-2 YesY
ATC code ?
Chemical data
Formula C19H23N 
Mol. mass 265.39 g/mol

Diphenidine (1-(1,2-diphenylethyl)piperidine) is a dissociative anesthetic drug that has been sold online as a research chemical.[1] The synthesis of diphenidine was first reported in 1924, and employed a nitrile displacement reaction analogous to the one that would later be used to discover phencyclidine in 1956.[1] Shortly after the 2013 UK ban on arylcyclohexylamines, diphenidine and the related compound methoxphenidine became available on the gray market. Anecdotal reports describe high doses of diphenidine producing "bizarre somatosensory phenomena and transient anterograde amnesia."[1] Diphenidine and related diarylethylamines have been studied in vitro as treatments for neurotoxic injury and are antagonists of the NMDA receptor.[2][3][4] Recent electrophysiological analysis demonstrates that the amplitude of NMDA-mediated fEPSPs are reduced by diphenidine and ketamine to a similar extent, with diphenidine displaying a slower onset of antagonism.[4] Though vendors of diphenidine have stated the compound "acts on dopamine transport" to date diphenidine has not been screened for affinity at the dopamine transporter.[1] In dogs diphenidine exhibits greater antitussive potency than codeine phosphate.[5]

In 2014 a package of herbal incense sold in the Shizuoka Prefecture under the name "Aladdin (sic) Spacial Edition" was found to contain diphenidine and 5-fluoro-AB-PINACA at concentrations of 289 mg/g and 55.5 mg/g, respectively.[6]

See also[edit]

References[edit]

  1. ^ a b c d Morris, H.; Wallach, J. (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 
  2. ^ EP 0346791, Gray NM, Cheng BK, "1,2-diarylethylamines for treatment of neurotoxic injury" 
  3. ^ Berger, M. L.; Schweifer, A.; Rebernik, P.; Hammerschmidt, F. (2009). "NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds". Bioorganic & Medicinal Chemistry 17 (9): 3456. doi:10.1016/j.bmc.2009.03.025.  edit
  4. ^ a b Wallach, J.; Kavanagh, P.; McLaughlin, G.; Morris, N.; Power, J.; Elliott, S.; Mercier, M.; Lodge, D.; Morris, H.; Dempster, N.; Brandt, S. (2014). "Preparation and characterization of the ‘research chemical’ diphenidine, its pyrrolidine analogue, and their 2,2-diphenylethyl isomers". Drug Testing and Analysis. 
  5. ^ Kasé, Y.; Yuizono, T. (1961). "Piperidino Groups in Antitussive Activity". J. Med. Chem. 
  6. ^ Wurita, A.; Hasegawa, K. (2014). "A large amount of new designer drug diphenidine coexisting with a synthetic cannabinoid 5-fluoro-AB-PINACA found in a dubious herbal product". Forensic Toxicology.