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The cis -stereoisomers of Δ 9 -THC [(-)- 3 and (+)- 3 ] were identified and quantified in a series of low-THC-containing varieties of Cannabis sativa registered in Europe as fiber hemp and in research accessions of cannabis. While Δ 9 - cis -THC ( 3 ) occurs in cannabis fiber hemp in the concentration range of (-)-Δ 9 - rans -THC [(-)- 1 ], it was undetectable in a sample of high-THC-containing medicinal cannabis. Natural Δ 9 - cis -THC ( 3 ) is scalemic (ca. 80-90% enantiomeric purity), and the absolute configuration of the major enantiomer was established as 6a S ,10a R [(-)- 3 ] by chiral chromatographic comparison with a sample available by asymmetric synthesis. The major enantiomer, (-)-Δ 9 - cis -THC [(-)- 3 ], was characterized as a partial cannabinoid agonist in vitro and elicited a full tetrad response in mice at 50 mg/kg doses. The current legal discrimination between narcotic and non-narcotic cannabis varieties centers on the contents of "Δ 9 -THC and isomers" and needs therefore revision, or at least a more specific wording, to account for the presence of Δ 9 - cis -THCs [(+)- 3 and (-)- 3 ] in cannabis fiber hemp varieties.

Δ9-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology

Δ⁹-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology