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Diphenidine (1,2-DEP, DPD, DND) is a dissociative anesthetic drug that has been sold online as a research chemical. 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. 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." Diphenidine and related diarylethylamines have been studied in vitro as treatments for neurotoxic injury and are antagonists of the NMDA receptor. 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. 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. 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. In dogs diphenidine exhibits greater antitussive potency than codeine phosphate.
Since 2014 there have been several published reports of diphenidine being sold in combination with other research chemicals, particularly synthetic cannabinoids in Japanese herbal incense blends. The first reported seizure concerned a Japanese product called "fragrance powder" containing diphenidine and benzylpiperazine. 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. Another product called ‘‘Herbal Incense. The Super Lemon’’ containing AB-CHMINACA, 5F-AMB, and diphenidine was implicated in a fatal poisoning.
- 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. PMID 24678061. doi:10.1002/dta.1620.
- EP 0346791, Gray NM, Cheng BK, "1,2-diarylethylamines for treatment of neurotoxic injury"
- 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.
- Kasé, Y.; Yuizono, T. (1961). "Piperidino Groups in Antitussive Activity". J. Med. Chem. 6: 118–122. doi:10.1021/jm00338a007.
- 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.
- 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.
- 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.
- 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.
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