Fentanyl tropane

Fentanyl tropane
Identifiers
  • N-phenyl-N-[(1R,5S)-8-(2-phenylethyl)-8-azabicyclo[3.2.1]octan-3-yl]propanamide
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC24H30N2O
Molar mass362.517 g·mol−1
3D model (JSmol)
  • CCC(=O)N(C1C[C@H]2CC[C@@H](C1)N2CCC3=CC=CC=C3)C4=CC=CC=C4
  • InChI=1S/C24H30N2O/c1-2-24(27)26(20-11-7-4-8-12-20)23-17-21-13-14-22(18-23)25(21)16-15-19-9-5-3-6-10-19/h3-12,21-23H,2,13-18H2,1H3/t21-,22+,23?
  • Key:OLHSRBZZORBSLQ-AIZNXBIQSA-N

Fentanyl tropane (tropafentanyl) is an opioid derivative which is an analogue of fentanyl, where the central piperidine ring has been bridged with a two carbon chain to form a tropane ring. It is made from tropinone in a similar manner to how fentanyl is made from 4-piperidone, and has two isomers, with the 3β isomer being around half the potency of fentanyl while the 3α isomer is much weaker, only around the same potency as morphine.

See also

References

  1. ↑ Riley TN, Bagley JR (October 1979). "4-Anilidopiperidine analgesics. 2. A study of the conformational aspects of the analgesic activity of the 4-anilidopiperidines utilizing isomeric N-substituted 3-(propananilido)nortropane analogues". Journal of Medicinal Chemistry. 22 (10): 1167–71. doi:10.1021/jm00196a004. PMID 513063.
  2. ↑ Lednicer D (1982). Central Analgetics. Wiley. p. 188-189. ISBN 0-471-08314-3.