Fentanyl azepane - Misplaced Pages

Chemical compound

Pharmaceutical compound

Fentanyl azepane
Identifiers

IUPAC name N-phenyl-N-propanamide
PubChem CID	12666096
Chemical and physical data
Formula	C₂₃H₃₀N₂O
Molar mass	350.506 g·mol
3D model (JSmol)	Interactive image
SMILES CCC(=O)N(C1CCCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
InChI InChI=1S/C23H30N2O/c1-2-23(26)25(21-12-7-4-8-13-21)22-14-9-17-24(19-16-22)18-15-20-10-5-3-6-11-20/h3-8,10-13,22H,2,9,14-19H2,1H3 Key:DJCBYHBSPDXQNT-UHFFFAOYSA-N

Fentanyl azepane (Fentanyl azepane homologue) is an opioid derivative which is a homologue of fentanyl, where the central piperidine ring has been expanded to an azepane ring. It is many times less potent than fentanyl itself, being only slightly stronger than morphine, but is still more potent than the ring-contracted pyrrolidine derivative, as well as other related compounds such as benzylfentanyl and ethoheptazine. The β-hydroxy derivative is slightly more potent again, as with betahydroxyfentanyl.

References

Finney ZG, Riley TN (August 1980). "4-Anilidopiperidine analgesics. 3. 1-Substituted 4-(propananilido)perhydroazepines as ring-expanded analogues". Journal of Medicinal Chemistry. 23 (8): 895–9. doi:10.1021/jm00182a016. PMID 7190616.
Deruiter J, Andurkar S, Riley TN, Walters DE, Noggle Jr FT (1992). "Investigation of the synthesis and analgesic activity of 1-substituted 4-(propananilido) perhydroazepines". Journal of Heterocyclic Chemistry. 29 (4): 779–786. doi:10.1002/jhet.5570290417.
Vardanyan RS, Hruby VJ (March 2014). "Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications". Future Medicinal Chemistry. 6 (4): 385–412. doi:10.4155/fmc.13.215. PMC 4137794. PMID 24635521.