Synthesis of [13C4]-labeled ∆9-tetrahydrocannabinol and 11-nor-9-carboxy-∆9-tetrahydrocannabinol as internal standards for reducing ion supressing/alteration effects in LC/MS-MS quantification
Journal article, Peer reviewed
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http://hdl.handle.net/11250/2359571Utgivelsesdato
2014Metadata
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Sammendrag
(−)-Δ9-Tetrahydrocannabinol is the principal psychoactive component of the
cannabis plant and also the active ingredient in some prescribed drugs. To detect and
control misuse and monitor administration in clinical settings, reference samples
of the native drugs and their metabolites are needed. The accuracy of liquid
chromatography/mass spectrometric quantification of drugs in biological samples depends
among others on ion suppressing/alteration effects. Especially, 13C-labeled drug analogues
are useful for minimzing such interferences. Thus, to provide internal standards for more
accurate quantification and for identification purpose, synthesis of [13C4]-Δ9-tetrahydrocannabinol
and [13C4]-11-nor-9-carboxy-Δ9-tetrahydrocannabinol was developed via
[13C4]-olivetol. Starting from [13C4]-olivetol the synthesis of [13C4]-11-nor-9-carboxy-Δ9-
tetrahydrocannabinol was shortened from three to two steps by employing nitromethane as a
co-solvent in condensation with (+)-apoverbenone.