Tetrahydrocannabiphorol

Not to be confused with Tetrakis(hydroxymethyl)phosphonium chloride (THPC).
See also: Cannabidiphorol (CBDP)
Tetrahydrocannabiphorol
Clinical data
Pronunciation/tɛtʃrəhaɪʒroʊkənæbɪfoʊrɔːl/
Other names(-)-Trans-Δ9-tetrahydrocannabiphorol,
Δ9-THCP,
(C7)-Δ9-THC,
THC-Heptyl
Drug classCannabinoid
Identifiers
  • (6aR,10aR)-3-heptyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H34O2
Molar mass342.523 g·mol−1
3D model (JSmol)
  • CCCCCCCc3cc2OC(C)(C)[C@@H]1CCC(C)=C[C@H]1c2c(O)c3
  • InChI=1S/C23H34O2/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/h13-15,18-19,24H,5-12H2,1-4H3/t18-,19-/m1/s1
  • Key:OJTMRZHYTZMJKX-RTBURBONSA-N

Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB1 and CB2 receptor agonist which was known as a synthetic homologue of tetrahydrocannabinol (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]

THCP was studied by Roger Adams as early as 1942.[5]

  1. ^ 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. PMID 2992174.
  2. ^ Bueno 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. PMID 33565878. S2CID 231866062.
  3. ^ 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. PMID 34517579.
  4. ^ Citti C, Linciano P, Russo F, Luongo L, Iannotta M, Maione S, et al. (December 2019). "A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol: Δ9-Tetrahydrocannabiphorol". Scientific Reports. 9 (1): 20335. Bibcode:2019NatSR...920335C. doi:10.1038/s41598-019-56785-1. PMC 6937300. PMID 31889124.
  5. ^ 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.