J Nat Prod. 2021 Jul 25. doi: 10.1021/acs.jnatprod.1c00513. Online ahead of print.

ABSTRACT

The cis-stereoisomers of Δ9-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 Δ9cis-THC (3) occurs in cannabis fiber hemp in the concentration range of (-)-Δ9trans-THC [(-)-1], it was undetectable in a sample of high-THC-containing medicinal cannabis. Natural Δ9cis-THC (3) is scalemic (ca. 80-90% enantiomeric purity), and the absolute configuration of the major enantiomer was established as 6aS,10aR [(-)-3] by chiral chromatographic comparison with a sample available by asymmetric synthesis. The major enantiomer, (-)-Δ9cis-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 « Δ9-THC and isomers » and needs therefore revision, or at least a more specific wording, to account for the presence of Δ9cis-THCs [(+)-3 and (-)-3] in cannabis fiber hemp varieties.

PMID:34304557 | DOI:10.1021/acs.jnatprod.1c00513


Source: ncbi 2

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