Diphenidine

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Diphenidine
Diphenidine.svg
Systematic (IUPAC) name
(±)-1-(1,2-Diphenylethyl)piperidine
Identifiers
CAS Registry Number 36794-52-2 YesY
ChemSpider 179031
Chemical data
Formula C19H23N
Molecular mass 265.39 g/mol
Physical data
Melting point 210 °C (410 °F)


Diphenidine (1,2-DEP, DPD, DND) is a dissociative anesthetic that has been sold 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.[1] 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] 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] The two enantiomers of diphenidine differ greatly in their ability to block the NMDA receptor, with the more potent (S)-enantiomer possessing affinity forty times higher than the (R)-enantiomer.[3] 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]

Since 2014 there have been several published reports of diphenidine being sold in combination with other research chemicals, particularly synthetic cannabinoids and stimulants in Japanese herbal incense blends.[6][7][8] The first reported seizure concerned a Japanese product called "fragrance powder" containing diphenidine and benzylpiperazine.[9] A 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] A product called ‘‘Herbal Incense. The Super Lemon’’ containing AB-CHMINACA, 5F-AMB, and diphenidine was implicated in a fatal poisoning.[7] Most recently diphenidine consumed in conjunction with three substituted cathinones, three benzodiazepines, and alcohol was implicated in a fatal ingestion of "bath salt" and "liquid aroma" products in Japan.[10]

See also[edit]


References[edit]

  1. ^ a b c d e 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: 614–32. doi:10.1002/dta.1620. PMID 24678061. 
  2. ^ EP 0346791, Gray NM, Cheng BK, "1,2-diarylethylamines for treatment of neurotoxic injury" 
  3. ^ a b 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. doi:10.1002/dta.1689. 
  5. ^ Kasé, Y.; Yuizono, T. (1961). "Piperidino Groups in Antitussive Activity". J. Med. Chem. 6: 118–122. doi:10.1021/jm00338a007. 
  6. ^ a b 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 32: 331–337. doi:10.1007/s11419-014-0240-y. 
  7. ^ a b Hasegawa, K.; Wurita, A. (2014). "Postmortem distribution of AB-CHMINACA, 5-fluoro-AMB, and diphenidine in body fluids and solid tissues in a fatal poisoning case: usefulness of adipose tissue for detection of the drugs in unchanged forms". Forensic Toxicology 33: 45–53. doi:10.1007/s11419-014-0245-6. 
  8. ^ Uchiyama, N.; Shimokawa, Y. (2014). "A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N–OH-EDMA, and a cathinone derivative dimethoxy-a-PHP, newly identified in illegal products". Forensic Toxicology. doi:10.1007/s11419-015-0268-7. 
  9. ^ Minakata, K.; Yamagishi, I. (2015). "Diphenidine and its metabolites in blood and urine analyzed by MALDI-Q-TOF mass spectrometry". Forensic Toxicology. doi:10.1007/s11419-015-0273-x. 
  10. ^ Kudo, K. (2015). "A fatal case of poisoning related to new cathinone designer drugs, 4-methoxy PV8, PV9, and 4-methoxy PV9, and a dissociative agent, diphenidine". Legal Medicine. doi:10.1016/j.legalmed.2015.06.005.