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Conformational analogies of morphine agonists and antagonists as revealed by carbon-13 NMR spectroscopy

✍ Scribed by Ernest L. Eliel; Susan Morris-Natschke; Vera M. Kolb

Publisher: John Wiley and Sons
Year: 1984
Tongue: English
Weight: 465 KB
Volume: 22
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1270220413

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✦ Synopsis

The extreme similarity (except in the vicinity of the nitrogen atom) of the 13C spectra of the agonist-antagonist pairs oxymorphone-naloxone and morphine-nalorphine and their respective hydrochlorides suggests that the N-methyl and N-aUyl compounds have analogous conformations. This makes unlikely an interpretation of the agonist-antagonist dichotomy in terms of confonnational differences. Both morphine hydrochloride and nalorphine hydrochloride exist as mixtures of two diastereomers: ca 83% of the isomer with equatorial N-akyl and 17% of the isomer with axial N-aikyl (AG'=O.95 kcalmol-I).

has both agonist and antagonist binding sites, the latter responding specifically to N-ally1 (and also to

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