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Synthesis of [1‐ 3 H]morphine‐6‐β‐D‐glucuronide
Author(s) -
Berrang Bertold D.,
Wyrick Christopher D.,
Carroll F. Ivy,
Seltzman Herbert H.
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199909)42:9<851::aid-jlcr247>3.0.co;2-g
Subject(s) - chemistry , glucuronidation , yield (engineering) , solvolysis , glucuronide , chromatography , morphine , liquid scintillation counting , high performance liquid chromatography , radiochemistry , organic chemistry , hydrolysis , metabolism , biochemistry , pharmacology , medicine , materials science , metallurgy , enzyme , microsome
Tritiated morphine of high specific activity was protected at the 3‐position by acetylation and subjected to glucuronidation by Koenigs‐Knorr procedure with methyl 2,3,4‐tri‐0‐acetyl‐1‐bromo‐1‐deoxy‐D‐glucopyranuronate and silver carbonate. Fully protected morphine‐6‐glucuronide was obtained in 42% yield and 95% radiochemical purity as determined by TLC‐RAM. Alkali catalyzed solvolysis in two steps furnished [1‐ 3 H]morphine‐6‐β‐D‐glucuronide in 23% overall radiochemical yield and 99% radio‐chemical purity determined by HPLC‐liquid scintillation counting and TLC‐RAM. Copyright © 1999 John Wiley & Sons, Ltd.