GC-MS Metabolite Profile and Identification of Unusual Homologous Cannabinoids in High Potency Cannabis sativa.

Phytochemical investigation of the lipids extracted from seeds of by GC-MS showed 43 cannabinoids, 16 of which are new. The extract is dominated by Δ-tetrahydrocannabinolic acid (A) and its neutral derivative -Δ-tetrahydrocannabinol-C (THC) and -Δ-tetrahydrocannabinol-C isomers with an ethyl-pentyl branched chain together with minor amounts of -Δ-tetrahydrocannabinol with a methyl-pentyl C branched side chain were identified as new natural compounds. Four cannabichromene isomers with a C side chain are postulated to be derived from the double bond migration at the terminal isoprenyl unit. C cannabichromene together with the neutral and acidic forms of cannabinol-C were also detected. The mass spectrum of these homologues as trimethylsilyl (TMS) derivatives are presented, and the fragmentation patterns are discussed.