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

Schafroth, Michael A; Mazzoccanti, Giulia; Reynoso-Moreno, Ines; Erni, Reto; Pollastro, Federica; Caprioglio, Diego; Botta, Bruno; Allegrone, Gianna; Grassi, Giulio; Chicca, Andrea; Gasparrini, Francesco; Gertsch, Jürg; Carreira, Erick M; Appendino, Giovanni (2021). Δ9-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology. Journal of natural products, 84(9), pp. 2502-2510. American Chemical Society 10.1021/acs.jnatprod.1c00513

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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 Δ9-cis-THC (3) occurs in cannabis fiber hemp in the concentration range of (-)-Δ9-trans-THC [(-)-1], it was undetectable in a sample of high-THC-containing medicinal cannabis. Natural Δ9-cis-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, (-)-Δ9-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 "Δ9-THC and isomers" and needs therefore revision, or at least a more specific wording, to account for the presence of Δ9-cis-THCs [(+)-3 and (-)-3] in cannabis fiber hemp varieties.

Item Type:

Journal Article (Original Article)

Division/Institute:

04 Faculty of Medicine > Pre-clinic Human Medicine > Institute of Biochemistry and Molecular Medicine

UniBE Contributor:

Reynoso, Ines del Carmen; Chicca, Andrea and Gertsch, Jürg

Subjects:

500 Science > 570 Life sciences; biology
600 Technology > 610 Medicine & health

ISSN:

0163-3864

Publisher:

American Chemical Society

Language:

English

Submitter:

Barbara Franziska Järmann-Bangerter

Date Deposited:

02 Dec 2021 09:26

Last Modified:

02 Dec 2021 09:26

Publisher DOI:

10.1021/acs.jnatprod.1c00513

PubMed ID:

34304557

BORIS DOI:

10.48350/161548

URI:

https://boris.unibe.ch/id/eprint/161548

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