Premium
Configurational Analysis of Thebaine, Codeine and 14β‐Hydroxycodeinone N ‐Oxides
Author(s) -
Caldwell Gary W.,
Diane Gauthier A.,
Mills John E.
Publication year - 1996
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199607)34:7<505::aid-omr913>3.0.co;2-y
Subject(s) - thebaine , chemistry , methiodide , codeine , oxide , free base , proton nmr , carbon 13 nmr , stereochemistry , organic chemistry , morphine , pharmacology , medicine , salt (chemistry)
The 1 H (400 MHz) and 13 C (100 MHz) NMR peak assignments of thebaine derivatives [free base (1), hydrochloride (2 and 3), methiodide (4) and N ‐oxides (5 and 6)], codeine N ‐oxide (7) and 14β‐hydroxycodeinone N ‐oxide (8) were performed using various one‐ and two‐dimensional techniques. The configurations of the quaternary nitrogen‐substituted alkaloids were determined. The reaction of thebaine, codeine and 14β‐hydroxycodeinone with H 2 O 2 produced thebaine N ‐oxide with the major product (6; R f 0.62) having an N ‐CH 3 axial configuration and both codeine N ‐oxide (7; R f 0.40) and 14β‐hydroxycodeinone N ‐oxide (8; R f 0.73) with the major product having an N ‐CH 3 equatorial configuration.