Chemistry:Diphenpipenol

From HandWiki
Short description: Chemical compound
Diphenpipenol
Diphenpipenol Structure.svg
Clinical data
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC25H28N2O2
Molar mass388.511 g·mol−1
3D model (JSmol)

Diphenpipenol is an opioid analgesic drug invented in the 1970s by Dainippon Pharmaceutical Co.[1] 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.[2] 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.[3]

Alternate isomer sold as diphenpipenol

See also

References

  1. Nishimura H, Uno H, Natsuka, Shimokawa N, Shimizu M, Nakamura H, "1-Substituted-4-(1,2-diphenylethyl)piperazine derivatives and compositions containing the same.", US patent 4080453, issued 21 March 1978, assigned to Dainippon Pharmaceutical Co Ltd
  2. "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. October 1987. doi:10.1021/jm00393a017. PMID 3656354. 
  3. "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. June 2020. doi:10.1093/jat/bkaa066. PMID 32514558.