Fentanyl tropane

Fentanyl tropane
Identifiers
	IUPAC name N-phenyl-N-[(1R,5S)-8-(2-phenylethyl)-8-azabicyclo[3.2.1]octan-3-yl]propanamide;
PubChem CID	118718255;
Chemical and physical data
Formula	C24H30N2O
Molar mass	362.517 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=O)N(C1C[C@H]2CC[C@@H](C1)N2CCC3=CC=CC=C3)C4=CC=CC=C4;
	InChI 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.^[1]^[2]

References

^ 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.
^ Lednicer D (1982). Central Analgetics. Wiley. p. 188-189. ISBN 0-471-08314-3.

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[pmid513063-1] 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.

[1]

[2]

See also

References