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A method for the structural determination of cannabichromene metabolites by mass spectrometry
Author(s) -
Harvey D. J.,
Brown N. K.
Publication year - 1990
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290040411
Subject(s) - chemistry , fragmentation (computing) , trimethylsilyl , hydroxylation , mass spectrometry , ion , chromatography , rhodium , medicinal chemistry , catalysis , organic chemistry , enzyme , computer science , operating system
Abstract Ready identification of hydroxy metabolites of cannabichromene (CBC) by mass spectrometry of their trimethylsilyl derivatives is prevented by the dominant fragmentation to give a substituted chromenyl ion; this suppresses ions diagnostic of the position of metabolic hydroxylation. To overcome this difficulty, metabolites were hydrogenated over a rhodium/alumina catalyst to reduce the double bond responsible for chromenyl ion formation and to redirect the fragmentation to the site of metabolic attack. This resulted in the production of abundant diagnostic fragment ions enabling all monohydroxy‐CBCs to be readily identified.