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, 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: |
05 Dec 2022 15:55 |
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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