Constituents of cannabis sativa, L. VIII: Possible biological application of a new method to separate cannabidiol and cannabichromene

Synthetic and naturally occurring cannabidiol and cannabichromene were distinctly separated without derivation by GLC using a 6% OV-1 column; an artifact of cannabichromene, cannabicyclol, was separated from (−)-Δ⁹-trans-tetrahydrocanna-bivarin. This procedure is versatile and applicable for the quantitation of Cannabis containing both cannabidiol and cannabichromene. Biological interaction among (−)-Δ⁹-trans-tetrahydrocannabinol, cannabichromene, and other cannabinoids in natural Cannabis preparations can now be studied. In the phenyl methyl silicone polymer series, cannabidiol precedes cannabichromene on columns containing below a 50% phenyl-to-methyl ratio. Columns containing a 50:50 or greater ratio of phenyl to methyl reverse the separation order with cannabichromene preceding cannabidiol.