Hexahydrocannabiphorol

Hexahydrocannabiphorol

Identifiers
IUPAC name (6aR,10aR)-6,6,9-trimethyl-3-heptyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
CAS Number	3051970-87-4  Y
Chemical and physical data
Formula	C23H36O2
Molar mass	344.539 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCCCc1cc2OC(C)(C)[C@@H]3CCC(C)C[C@H]3c2c(O)c1
InChI InChI=InChI=1S/C23H36O2/c1-5-6-7-8-9-10-17-14-20(24)22-18-13-16(2)11-12-19(18)23(3,4)25-21(22)15-17/h14-16,18-19,24H,5-13H2,1-4H3/t16?,18-,19-/m1/s1 Key:USZILQYXSONCHH-VOBHOPKGSA-N

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]

Pharmacology

HHC-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 gray market cannabis products in the United States. ^[1]

Legality

The legal status of hexahydrocannabinol and derivatives varies between countries, leading to widespread sale in some parts of 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

• Tetrahydrocannabiphorol
• Canbisol
• CP 42,096
• HHC-acetate
• Hexahydrocannabihexol
• HHCP-O-acetate
• THCP-O-acetate

References

1. 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.
2. 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.
3. Hexahydrocannabinol (HHC) and related substances. European Monitoring Centre for Drugs and Drug Addiction, 2023
4. 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. Bibcode:1942JAChS..64..694A. doi:10.1021/ja01255a061.
5. 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. 17 (4): 487–493. doi: 10.1002/dta.3750 . PMC   11994375 . PMID   38894658.
6. "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.
7. "Japan decides to ban more cannabinoids after gummies sicken people". Kyodo News. 26 December 2023.