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Electron impact‐induced fragmentation of the trimethylsilyl derivatives of monohydroxy‐hexahydrocannabinols
Author(s) -
Harvey D. J.,
Brown N. K.
Publication year - 1991
Publication title -
biological mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1052-9306
DOI - 10.1002/bms.1200200510
Subject(s) - lithium aluminium hydride , chemistry , trimethylsilyl , fragmentation (computing) , electron ionization , catalysis , hydrogen peroxide , mass spectrometry , medicinal chemistry , mass spectrum , organic chemistry , ion , combinatorial chemistry , chromatography , computer science , ionization , operating system
Monohydroxylated derivatives of hexahydrocannabinols were synthesized by catalytic hydrogenation of hydroxytetrahydrocannabinols over a rhodium/alumina catalyst, reduction of tetrahydrocannabinol epoxides with lithium aluminium hydride, or by reaction of tetrahydrocannabinols with hydrogen peroxide. The electron impact‐induced fragmentation of their trimethylsilyl ethers was investigated with the aid of deuterium labelling. Most of the compounds gave characteristically different mass spectra with abundant, diagnostically useful fragment ions. As hexahydrocannabinols containing hydroxy groups in all metabolically sensitive positions were readily prepared by the above methods, these provided reference samples for identification of new hydroxylated metabolites of isomeric tetrahydrocannabinols following hydrogenation. The method was validated by application to metabolites of delta‐9(11)‐tetrahydrocannabinol.