Hexahydrocannabiphorol (HHCP, sometimes mistakenly referred to as hexahydroxycannabiphorol) is a semi-synthetic cannabinoid derivative which has been marketed since around 2021.[1][2] It is believed to be made from the hydrogenation of tetrahydrocannabiphorol (THCP). THCP is only reported as a trace component of cannabis in 2019.[3] HHCP was studied by Roger Adams as early as 1942.[4]
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| Identifiers | |
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| Chemical and physical data | |
| Formula | C23H36O2 |
| Molar mass | 344.539 g·mol−1 |
| 3D model (JSmol) | |
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Pharmacology
editHHC-P is a partial agonist of the CB1 receptors with an EC50 of 44.4nM for 9R-HHCP and 134nM for 9S-HHCP. Compared to Hexahydrocannabinol (HHC) with an EC50 of 101nM for 9R-HHC and 1,190nM for 9S-HHC[5] In 2021, HHC-P was positively identified in multiple retail electronic vaping products in the United States.[1]
Legality
editThe legal status of hexahydrocannabinol and derivatives varies between countries, leading to widespread sale in some jurisdictions in Europe and the US.
In France, HHCP was banned in 2023.[6]
In Japan, Japanese Health Ministry announced that six synthetic cannabinoids with structures similar to HHCH, including HHCP, were to be banned from 6 January 2024[7]
HHCP was banned in Slovakia as of 13 January 2024.[citation needed]
See also
editReferences
edit- ^ a b Tanaka R, Kikura-Hanajiri R (June 2023). "Identification of hexahydrocannabinol (HHC), dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC) and hexahydrocannabiphorol (HHCP) in electronic cigarette cartridge products". Forensic Toxicology. 42 (1): 71–81. doi:10.1007/s11419-023-00667-9. PMID 37365398. S2CID 259259903.
- ^ Höfert L, Becker S, Dreßler J, Baumann S (August 2023). "Quantification of (9R)- and (9S)-hexahydrocannabinol (HHC) via GC-MS in serum/plasma samples from drivers suspected of cannabis consumption and immunological detection of HHC and related substances in serum, urine, and saliva". Drug Testing and Analysis. 16 (5): 489–497. doi:10.1002/dta.3570. PMID 37652872. S2CID 261430819.
- ^ Hexahydrocannabinol (HHC) and related substances. European Monitoring Centre for Drugs and Drug Addiction, 2023
- ^ Adams R, Loewe S, Smith CM, McPhee WD (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII1". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.
- ^ Persson M, Kronstrand R, Evans-Brown M, Green H (June 2024). "In vitro activation of the CB1 receptor by the semi-synthetic cannabinoids hexahydrocannabinol (HHC), hexahydrocannabinol acetate (HHC-O) and hexahydrocannabiphorol (HHC-P)". Drug Testing and Analysis. doi:10.1002/dta.3750. PMID 38894658.
- ^ "Actualité - L'ANSM classe l'hexahydrocannabinol (HHC) et deux de ses dérivés sur la liste des stupéfiants" [News - The ANSM classifies hexahydrocannabinol (HHC) and two of its derivatives on the list of narcotics]. Agence nationale de sécurité du médicament et des produits de santé (ANSM) (in French). Retrieved 2023-06-12.
- ^ "Japan decides to ban more cannabinoids after gummies sicken people". Kyodo News. 26 December 2023.
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