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Synthesis and pharmacological activity of the epimers of hexahydrocannabinol (HHC). | LitMetric

AI Article Synopsis

  • Cannabis has both therapeutic benefits and controversial psychoactive effects, largely influenced by CB1 receptors, with Δ9-THC being responsible for the high and CBD offering different pharmacological effects.
  • The popularity of cannabis has led to the inclusion of semi-synthetic derivatives like hexahydrocannabinol (HHC) in products, which mimic Δ9-THC effects to bypass legal barriers.
  • This study focused on synthesizing and characterizing HHC epimers and developed a rapid chromatographic method to analyze major cannabinoids and HHC in commercial cannabis samples.

Article 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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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10329643PMC
http://dx.doi.org/10.1038/s41598-023-38188-5DOI Listing

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