Published: Journal of Analytical Toxicology, Volume 22, Number 7, November/December 1998, pp. 567-572
In Vivo Formation of Codeinone-Glutathione Adduct: Isolation
and Identification of a New Metabolite in the Bile of Codeine-Treated Guinea
Pig
Takashi Ishida, Masashi Yano, and Satoshi Toki
Codeinone-glutathione adduct (CO-GSH) in the bile of guinea pigs given a subcutaneous
injection of codeine was isolated and identified. Synthesized authentic CO-GSH
was characterized by the mass and nuclear magnetic resonance spectra and used
as the standard sample. The metabolite was isolated by preparative high-performance
liquid chromatography on a C18 column. The fractions containing the
conjugated metabolite were purified using Sep-Pak C18 cartridges.
For further purification of the metabolite CO-GSH, a Radial Pak CN column was
used. Structure assignment of the metabolite was then performed by fast-atom-bombardment
mass spectrometry and 500 MHz Fourier-transform-NMR spectrometric analysis and
identified as S-[4,5-epoxy-3-methoxy-17-methyl-6-oxo-morphinan-(8S)-yl]
glutathione.
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