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Synthesis and pharmacological activity of the epimers of hexahydrocannabinol (HHC)
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 psychot...
Autores principales: | , , , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Nature Publishing Group UK
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10329643/ https://www.ncbi.nlm.nih.gov/pubmed/37422571 http://dx.doi.org/10.1038/s41598-023-38188-5 |
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author | Russo, Fabiana Vandelli, Maria Angela Biagini, Giuseppe Schmid, Martin Luongo, Livio Perrone, Michela Ricciardi, Federica Maione, Sabatino Laganà, Aldo Capriotti, Anna Laura Gallo, Alfonso Carbone, Luigi Perrone, Elisabetta Gigli, Giuseppe Cannazza, Giuseppe Citti, Cinzia |
author_facet | Russo, Fabiana Vandelli, Maria Angela Biagini, Giuseppe Schmid, Martin Luongo, Livio Perrone, Michela Ricciardi, Federica Maione, Sabatino Laganà, Aldo Capriotti, Anna Laura Gallo, Alfonso Carbone, Luigi Perrone, Elisabetta Gigli, Giuseppe Cannazza, Giuseppe Citti, Cinzia |
author_sort | Russo, Fabiana |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-10329643 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-103296432023-07-10 Synthesis and pharmacological activity of the epimers of hexahydrocannabinol (HHC) Russo, Fabiana Vandelli, Maria Angela Biagini, Giuseppe Schmid, Martin Luongo, Livio Perrone, Michela Ricciardi, Federica Maione, Sabatino Laganà, Aldo Capriotti, Anna Laura Gallo, Alfonso Carbone, Luigi Perrone, Elisabetta Gigli, Giuseppe Cannazza, Giuseppe Citti, Cinzia Sci Rep Article 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. Nature Publishing Group UK 2023-07-08 /pmc/articles/PMC10329643/ /pubmed/37422571 http://dx.doi.org/10.1038/s41598-023-38188-5 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Russo, Fabiana Vandelli, Maria Angela Biagini, Giuseppe Schmid, Martin Luongo, Livio Perrone, Michela Ricciardi, Federica Maione, Sabatino Laganà, Aldo Capriotti, Anna Laura Gallo, Alfonso Carbone, Luigi Perrone, Elisabetta Gigli, Giuseppe Cannazza, Giuseppe Citti, Cinzia Synthesis and pharmacological activity of the epimers of hexahydrocannabinol (HHC) |
title | Synthesis and pharmacological activity of the epimers of hexahydrocannabinol (HHC) |
title_full | Synthesis and pharmacological activity of the epimers of hexahydrocannabinol (HHC) |
title_fullStr | Synthesis and pharmacological activity of the epimers of hexahydrocannabinol (HHC) |
title_full_unstemmed | Synthesis and pharmacological activity of the epimers of hexahydrocannabinol (HHC) |
title_short | Synthesis and pharmacological activity of the epimers of hexahydrocannabinol (HHC) |
title_sort | synthesis and pharmacological activity of the epimers of hexahydrocannabinol (hhc) |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10329643/ https://www.ncbi.nlm.nih.gov/pubmed/37422571 http://dx.doi.org/10.1038/s41598-023-38188-5 |
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