BIOTRANSFORMATION OF DOXYLAMINE - ISOLATION, IDENTIFICATION AND SYNTHESIS OF SOME METABOLITES

  • 1 January 1981
    • journal article
    • research article
    • Vol. 19  (7) , 485-490
Abstract
After administration of therapeutic doses of the antihistamine doxylamine, the unchanged drug and 5 degradation products were detected in human urine; their chemical structures are discussed and confirmed by synthesis. Biotransformation of doxylamine in man takes place by: successive dealkylations at the N atom, giving N-demethyl-doxylamine and N,N-didemethyl-doxylamine; cleavage at the benzhydrylether-function, causing the formation of 1-phenyl-1-(2-pyridyl)-ethanol, 1-phenyl-1-(2-pyridyl)-ethane(VI) and 1-phenyl-1-(2-pyridyl)-ethene(VII). The VI and VII may be artifacts. Identification of an additional degradation product (= IV) was not possible, as the isolated quantities were too small. The analytical properties of the pure substance and free base and the role of chemical ionization mass spectrometry with various reagent gases for the examination of biological extracts are discussed.

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