Diphenidine

Diphenidine
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Under Psychoactive Substances Act; UN: Psychotropic Schedule II;
Identifiers
	IUPAC name (±)-1-(1,2-Diphenylethyl)piperidine;
CAS Number	36794-52-2 ;
PubChem CID	206666;
ChemSpider	179031;
UNII	H8Q4VPL82Y;
KEGG	C22733;
ChEBI	CHEBI:104234;
ChEMBL	ChEMBL4303426;
CompTox Dashboard (EPA)	DTXSID50724547 ;
Chemical and physical data
Formula	C19H23N
Molar mass	265.400 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	210 °C (410 °F)
	SMILES c1ccc(cc1)CC(c2ccccc2)N3CCCCC3;
	InChI InChI=1S/C19H23N/c1-4-10-17(11-5-1)16-19(18-12-6-2-7-13-18)20-14-8-3-9-15-20/h1-2,4-7,10-13,19H,3,8-9,14-16H2; Key:JQWJJJYHVHNXJH-UHFFFAOYSA-N;

Diphenidine (1,2-DEP, DPD, DND) is a dissociative anesthetic that has been sold as a designer drug.^[2]^[3]^[4] Diphenidine was first synthesized in 1924 using a Bruylants reaction similar to the one later employed in the discovery of phencyclidine in 1956.^[2] Following the 2013 UK ban on arylcyclohexylamines, diphenidine and the related compound methoxphenidine emerged on the grey market.^[2] Anecdotal reports indicate that high doses of diphenidine can produce "bizarre somatosensory phenomena and transient anterograde amnesia."^[2]

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ ^a ^b ^c ^d 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.
^ Wink CS, Michely JA, Jacobsen-Bauer A, Zapp J, Maurer HH (October 2016). "Diphenidine, a new psychoactive substance: metabolic fate elucidated with rat urine and human liver preparations and detectability in urine using GC-MS, LC-MSⁿ , and LC-HR-MSⁿ". Drug Testing and Analysis. 8 (10): 1005–1014. doi:10.1002/dta.1946. PMID 26811026.
^ Helander A, Beck O, Bäckberg M (June 2015). "Intoxications by the dissociative new psychoactive substances diphenidine and methoxphenidine". Clinical Toxicology. 53 (5): 446–453. doi:10.3109/15563650.2015.1033630. PMID 25881797. S2CID 5962038.

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[Morris-2] 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.

[3] Wink CS, Michely JA, Jacobsen-Bauer A, Zapp J, Maurer HH (October 2016). "Diphenidine, a new psychoactive substance: metabolic fate elucidated with rat urine and human liver preparations and detectability in urine using GC-MS, LC-MSⁿ , and LC-HR-MSⁿ". Drug Testing and Analysis. 8 (10): 1005–1014. doi:10.1002/dta.1946. PMID 26811026.

[4] Helander A, Beck O, Bäckberg M (June 2015). "Intoxications by the dissociative new psychoactive substances diphenidine and methoxphenidine". Clinical Toxicology. 53 (5): 446–453. doi:10.3109/15563650.2015.1033630. PMID 25881797. S2CID 5962038.

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