Tetrahydrocannabiphorol (THCP) is a potentphytocannabinoid, a CB1 and CB2agonist which was known as a synthetic homologue of THC,[1] but for the first time in 2019 was isolated as a natural product in trace amounts from Cannabis sativa.[2][3] It is structurally similar to Δ9-THC, the main active component of cannabis, but with the pentyl side chain extended to heptyl. Since it has a longer side chain, its cannabinoid effects are "far higher than Δ9-THC itself." Tetrahydrocannabiphorol has a reported binding affinity of 1.2 nM at CB1, approximately 33 times that of Δ9-THC (40 nM at CB1).[4]
The Δ3/Δ6a(10a) isomer Δ3-THCP was synthesised in 1941, and was found to have around the same potency as Δ3-THC, unlike the hexyl homologue parahexyl which was significantly stronger.[6]
The Δ8 isomer is also known as a synthetic cannabinoid under the code name JWH-091.[7][8] It's unconfirmed whether or not Δ8-THCP is found naturally in cannabis plants, but likely is due to Δ8-THC itself being a degraded form of Δ9-THC.[9] JWH-091 has approximately double the binding affinity at the CB1 receptor (22 nM ± 3.9 nM) in comparison to Δ9-THC (40.7 nM ± 1.7 nM) or Δ8-THC (44 nM ± 12 nM),[8] but appears significantly lower in vitro than the binding activity of Δ9-THCP (Ki = 1.2 nM)[4]
The Δ9 isomer of THCP occurs naturally in cannabis, but in small amounts. A 2021 study reported the content of Δ9-THCP ranging from 0.0023% to 0.0136% (w/w) (approximately 0.02–0.13 mg/g) without correlation to THC percentage in Δ9-THC-dominant strains of cannabis; that study failed to detect THCP in CBD-dominant strains.[2][10]
^Harvey DJ (March 1985). "Identification of hepatic metabolites of n-heptyl-delta-1-tetrahydrocannabinol in the mouse". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 15 (3): 187–197. doi:10.3109/00498258509045349. PMID2992174.
^ abBueno J, Greenbaum EA (February 2021). "(-)-trans-Δ9-Tetrahydrocannabiphorol Content of Cannabis sativa Inflorescence from Various Chemotypes". Journal of Natural Products. 84 (2): 531–536. doi:10.1021/acs.jnatprod.0c01034. PMID33565878. S2CID231866062.
^Linciano P, Russo F, Citti C, Tolomeo F, Paris R, Fulvio F, et al. (December 2021). "The novel heptyl phorolic acid cannabinoids content in different Cannabis sativa L. accessions". Talanta. 235: 122704. doi:10.1016/j.talanta.2021.122704. hdl:11380/1250339. PMID34517579.
^Adams R, Loewe S, Jelinek C, Wolff H (July 1941). "Tetrahydrocannabinol Homologs with Marihuana Activity. IX". Journal of the American Chemical Society. 63 (7): 1971–1973. doi:10.1021/ja01852a052.