The structure of a human metabolite of pholcodine

J Gore, B Kasum, MA Holman, IM Scharfbillig…

Index: Gore, Jeff; Kasum, Bruno; Holman, Michelle A.; Scharfbillig, Ilse M.; Ward, David Australian Journal of Chemistry, 1996 , vol. 49, # 11 p. 1235 - 1242

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Citation Number: 4

Abstract

Abstract The structure of a metabolite of pholcodine produced by humans is shown, by spectroscopic and synthetic data, to be a morpholin-3-one (amide) derivative rather than the alternative morpholin-2-one (lactone) isomer. Acylation of diethanolamine leads to an N, O- diacyl product even when only 1 equiv. of acylating agent is used. A mechanism is proposed to account for this observation. The appropriately substituted diacyl product can be ...