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Diphenpipenol

Clinical data
ATC code	None
Identifiers
IUPAC name 3--2-phenylethyl]phenol
CAS Number	83374-54-3
PubChem CID	13236269
ChemSpider	15325002
UNII	ZK4VB64WSR
ChEMBL	ChEMBL1189795
CompTox Dashboard (EPA)	DTXSID901336845
Chemical and physical data
Formula	C25H28N2O2
Molar mass	388.511 g·mol
3D model (JSmol)	Interactive image
SMILES COc4ccccc4N1CCN(CC1)C(Cc2cccc(O)c2)c3ccccc3
InChI InChI=1S/C25H28N2O2/c1-29-25-13-6-5-12-23(25)26-14-16-27(17-15-26)24(21-9-3-2-4-10-21)19-20-8-7-11-22(28)18-20/h2-13,18,24,28H,14-17,19H2,1H3 Key:ILCZMFSACNEMGK-UHFFFAOYSA-N

Diphenpipenol is an opioid analgesic drug invented in the 1970s by Dainippon Pharmaceutical Co. It is chemically a 1-substituted-4-(1,2-diphenylethyl)piperazine derivative related to compounds such as MT-45 and AD-1211, but diphenpipenol is the most potent compound in the series, with the more active (S) enantiomer being around 105 times the potency of morphine in animal studies. This makes it a similar strength to fentanyl and its analogues, and consequently diphenpipenol can be expected to pose a significant risk of producing life-threatening respiratory depression, as well as other typical opioid side effects such as sedation, itching, nausea and vomiting.

Diphenpipenol has been offered for sale online as a designer drug, though analysis of a sample of supposed diphenpipenol found it to instead contain a structural isomer with much weaker opioid activity, and it is unclear if genuine diphenpipenol has actually been sold.

See also

• 3C-PEP
• Azaprocin
• Bucinnazine
• Diphenidine
• Lefetamine

References

1. US 4080453, Nishimura H, Uno H, Natsuka, Shimokawa N, Shimizu M, Nakamura H, "1-Substituted-4-(1,2-diphenylethyl)piperazine derivatives and compositions containing the same.", issued 21 March 1978, assigned to Dainippon Pharmaceutical Co Ltd 
2. Natsuka K, Nakamura H, Nishikawa Y, Negoro T, Uno H, Nishimura H (October 1987). "Synthesis and structure-activity relationships of 1-substituted 4-(1,2-diphenylethyl)piperazine derivatives having narcotic agonist and antagonist activity". Journal of Medicinal Chemistry. 30 (10): 1779–87. doi:10.1021/jm00393a017. PMID 3656354.
3. Cannaert A, Hulpia F, Risseeuw M, Van Uytfanghe K, Deconinck E, Van Calenbergh S, et al. (June 2020). "Report on a new opioid NPS: chemical and in vitro functional characterization of a structural isomer of the MT-45 derivative diphenpipenol". Journal of Analytical Toxicology. 45 (2): 134–140. doi:10.1093/jat/bkaa066. hdl:1854/LU-8664239. PMID 32514558.

• Drugs not assigned an ATC code
• Synthetic opioids
• Piperazines
• Mu-opioid receptor agonists
• Designer drugs