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Abstract
Cannabis is a multifaceted plant with numerous therapeutic properties on one hand, and controversial psychotropic activities on the other hand, which are modulated by CB1 endocannabinoid receptors. Δ9-Tetrahydrocannabinol (Δ9-THC) has been identified as the main component responsible for the psychotropic effects, while its constitutional isomer cannabidiol (CBD) has shown completely different pharmacological properties. Due to its reported beneficial effects, Cannabis has gained global popularity and is openly sold in shops and online. To circumvent legal restrictions, semi-synthetic derivatives of CBD are now frequently added to cannabis products, producing "high" effects similar to those induced by Δ9-THC. The first semi-synthetic cannabinoid to appear in the EU was obtained through cyclization and hydrogenation of CBD, and is known as hexahydrocannabinol (HHC). Currently, there is limited knowledge regarding HHC, its pharmacological properties, and its prevalence, as it is not commonly investigated in routine toxicological assays. In this study, synthetic strategies were explored to obtain an excess of the active epimer of HHC. Furthermore, the two epimers were purified and individually tested for their cannabinomimetic activity. Lastly, a simple and rapid chromatographic method employing a UV detector and a high-resolution mass spectrometer was applied to identify and quantify up to ten major phytocannabinoids, as well as the HHC epimers, in commercial cannabis samples.
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1 University of Modena and Reggio Emilia, Clinical and Experimental Medicine PhD Program, Modena, Italy (GRID:grid.7548.e) (ISNI:0000000121697570); University of Modena and Reggio Emilia, Department of Biomedical, Metabolic and Neural Sciences, Modena, Italy (GRID:grid.7548.e) (ISNI:0000000121697570)
2 University of Modena and Reggio Emilia, Department of Life Sciences, Modena, Italy (GRID:grid.7548.e) (ISNI:0000000121697570)
3 University of Modena and Reggio Emilia, Department of Biomedical, Metabolic and Neural Sciences, Modena, Italy (GRID:grid.7548.e) (ISNI:0000000121697570)
4 University of Graz, Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, Graz, Austria (GRID:grid.5110.5) (ISNI:0000000121539003)
5 Università Della Campania “L. Vanvitelli”, Division of Pharmacology, Department of Experimental Medicine, Naples, Italy (GRID:grid.5110.5)
6 Sapienza University of Rome, Department of Chemistry, Rome, Italy (GRID:grid.7841.a)
7 Istituto Zooprofilattico Sperimentale del Mezzogiorno, Department of Chemistry, Portici, Italy (GRID:grid.419577.9) (ISNI:0000 0004 1806 7772)
8 Institute of Nanotechnology – CNR NANOTEC, Lecce, Italy (GRID:grid.494551.8) (ISNI:0000 0004 6477 0549)
9 University of Modena and Reggio Emilia, Department of Life Sciences, Modena, Italy (GRID:grid.7548.e) (ISNI:0000000121697570); Institute of Nanotechnology – CNR NANOTEC, Lecce, Italy (GRID:grid.494551.8) (ISNI:0000 0004 6477 0549)