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The solute conformation of opioid ligands of the 4-arylpiperidine class: α-Promedol and related compounds

✍ Scribed by Alan F. Casy; Francis O. Ogungbamila

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
463 KB
Volume
30
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The NMR spectra (chiefly ^1^H) of isomeric 2,5‐ and 2,3‐dimethyl‐4‐phenyl‐4‐piperidinols, related esters and trans‐ 2,6‐dimethyl‐4‐propionyloxy‐4‐phenylpiperidine HCl (all N‐methylated) have been assigned and analysed in terms of solute conformation. Preferred forms include 4‐ax‐phenyl and 4‐eq‐phenyl chairs and, in the case of the γ‐2,3‐dimethyl‐4‐piperidinol base, a boat conformation. In several cases the existence of pairs of N‐protonated epimers has been demonstrated. The findings are important both to the conformational analysis of saturated six‐membered heterocycles and to stereoactivity analyses of opioid ligands of the 4‐arylpiperidine class.

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