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Fentanyl azepane

From Wikipedia, the free encyclopedia

Fentanyl azepane
Identifiers
  • N-phenyl-N-[1-(2-phenylethyl)azepan-4-yl]propanamide
PubChem CID
Chemical and physical data
FormulaC23H30N2O
Molar mass350.506 g·mol−1
3D model (JSmol)
  • CCC(=O)N(C1CCCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
  • 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.[1][2][3]

See also

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.



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This page was last edited on 28 March 2024, at 03:15
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