Journal Article

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

in Journal of Analytical Toxicology

Volume 22, issue 7, pages 567-572
Published in print November 1998 | ISSN: 0146-4760
Published online November 1998 | e-ISSN: 1945-2403 | DOI: http://dx.doi.org/10.1093/jat/22.7.567
In Vivo Formation of Codeinone-Glutathione Adduct: Isolation and Identification of a New Metabolite in the Bile of Codeine-Treated Guinea Pig

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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-oxomorphinan-(8S)-yl] glutathione.

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Subjects: Medical Toxicology ; Toxicology (Non-medical)

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