Hexahydrocannabivarin

Hexahydrocannabivarin
Identifiers
	IUPAC name (6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol;
Chemical and physical data
Formula	C19H28O2
Molar mass	288.431 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCc1cc2OC(C)(C)[C@@H]3CCC(C)C[C@H]3c2c(O)c1;
	InChI InChI=InChI=1S/C19H28O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h10-12,14-15,20H,5-9H2,1-4H3/t12?,14-,15-/m1/s1; Key:QYNCMPYNYFYQFE-JENMUQSASA-N;

Hexahydrocannabivarin (HHCV, HHC-V) is a semi-synthetic cannabinoid derivative, the hydrogenated derivative of tetrahydrocannabivarin (THCV). It was first synthesised by Roger Adams in 1942 and produces only weak cannabinoid-like effects in animals.^[1] More recently it has been sold as an ingredient in grey-market cannabinoid products. It has been investigated for potential antineoplastic activity in vitro.^[2]^[3]

References

^ Adams R, Loewe S, Smith CM, McPhee WD (March 1942). "Tetrahydrocannabinol homologs and analogs with marihuana activity. XIII". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.
^ Tesfatsion T, Collins A, Ramirez G, Mzannar Y, Khan H, Aboukameel O, Azmi A, Jagtap P, Ray K, Cruces W (2022). "Antineoplastic Properties of THCV, HHC, HHCV and their anti-Proliferative effects on HPAF-II, MIA-paca2, Aspc-1, and PANC-1 PDAC Pancreatic Cell Lines". ChemRxiv. doi:10.26434/chemrxiv-2022-v4zqc.
^ Docampo-Palacios ML, Ramirez GA, Tesfatsion TT, Okhovat A, Pittiglio M, Ray KP, Cruces W (September 2023). "Saturated Cannabinoids: Update on Synthesis Strategies and Biological Studies of These Emerging Cannabinoid Analogs". Molecules (Basel, Switzerland). 28 (17): 6434. doi:10.3390/molecules28176434. PMC 10490552. PMID 37687263.

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[1] Adams R, Loewe S, Smith CM, McPhee WD (March 1942). "Tetrahydrocannabinol homologs and analogs with marihuana activity. XIII". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.

[2] Tesfatsion T, Collins A, Ramirez G, Mzannar Y, Khan H, Aboukameel O, Azmi A, Jagtap P, Ray K, Cruces W (2022). "Antineoplastic Properties of THCV, HHC, HHCV and their anti-Proliferative effects on HPAF-II, MIA-paca2, Aspc-1, and PANC-1 PDAC Pancreatic Cell Lines". ChemRxiv. doi:10.26434/chemrxiv-2022-v4zqc.

[pmid37687263-3] Docampo-Palacios ML, Ramirez GA, Tesfatsion TT, Okhovat A, Pittiglio M, Ray KP, Cruces W (September 2023). "Saturated Cannabinoids: Update on Synthesis Strategies and Biological Studies of These Emerging Cannabinoid Analogs". Molecules (Basel, Switzerland). 28 (17): 6434. doi:10.3390/molecules28176434. PMC 10490552. PMID 37687263.

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See also

References