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Abstract
1. Urine from a dystonic patient treated with cannabidiol (CBD) was examined by g.l.c.-mass spectrometry for CBD metabolites. Metabolites were identified as their trimethylsilyl (TMS), [2H9]TMS, and methyl ester/TMS derivatives and as the TMS derivatives of the product of lithium aluminium deuteride reduction.
2. Thirty-three metabolites were identified in addition to unmetabolized CBD, and a further four metabolites were partially characterized.
3. The major metabolic route was hydroxylation and oxidation at C-7 followed by further hydroxylation in the pentyl and propenyl groups to give 1″-, 2″-, 3″-, 4″- and 10-hydroxy derivatives of CBD-7-oic acid. Other metabolites, mainly acids, were formed by β-oxidation and related biotransformations from the pentyl side-chain and these were also hydroxylated at C-6 or C-7. The major oxidized metabolite was CBD-7-oic acid containing a hydroxyethyl side-chain.
4. Two 8,9-dihydroxy compounds, presumably derived from the corresponding epoxide were identified.
5. Also present were several cyclized cannabinoids including delta-6- and delta-1-tetrahydrocannabinol and cannabinol.
6. This is the first metabolic study of CBD in humans; most observed metabolic routes were typical of those found for CBD and related cannabinoids in other species.