H4-CBD

H4-CBD
Names
IUPAC name
2-(2-Isopropyl-5-methylcyclohexyl)-5-pentylbenzene-1,3-diol
Other names
  • Hydrogenated CBD
  • HCBD
  • Tetrahydrocannabidiol
  • Cyclohexyl-CBD
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C21H34O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h12-15,17-18,22-23H,5-11H2,1-4H3
    Key: LXIXAVCVBZBXIY-UHFFFAOYSA-N
  • Oc1c(c(O)cc(c1)CCCCC)C2\CC(/CCC2\C(C)C)C
Properties
C21H34O2
Molar mass 318.501 g·mol−1
Related compounds
Related compounds
 H2-CBD
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

H4CBD (hydrogenated CBD, tetrahydrocannabidiol) is a synthetic cannabinoid that was first synthesized by Alexander R. Todd in 1940 derived from the catalytic hydrogenation of cannabidiol.

H2-CBD and 8,9-dihydrocannabidiol have also been referred to as "hydrogenated CBD", which may cause confusion.

Pharmacology

In 2006, it was discovered that H4CBD has a binding affinity of 145 nM at the CB1 receptor and potential anti-inflammatory effects independent of its cannabinoid receptor action. In contrast, CBD has been found to bind to the CB1 receptor as an inverse agonist/antagonist with a Ki ranging from 3.3 to 4.8 mM.

Elucidation

In 2023 H4CBD epimers were elucidated using NOESY and COSY NMR spectroscopic techniques, while the inclusion of LC-MS and SCFC were used to isolate individual diasteromers.

See also

References

  1. ↑ Jacob, A.; Todd, A. R. (1940). "119. Cannabis indica. Part II. Isolation of cannabidiol from Egyptian hashish. Observations on the structure of cannabinol". J. Chem. Soc. 119: 649–653. doi:10.1039/jr9400000649.
  2. ↑ Ben-Shabat, Shimon; Hanuš, Lumír O.; Katzavian, Galia; Gallily, Ruth (February 2006). "New Cannabidiol Derivatives: Synthesis, Binding to Cannabinoid Receptor, and Evaluation of Their Antiinflammatory Activity". Journal of Medicinal Chemistry. 49 (3): 1113–1117. doi:10.1021/jm050709m. PMID 16451075.
  3. ↑ Peng, Jiangling; Fan, Mingjie; An, Chelsea; Ni, Feng; Huang, Wendong; Luo, Jiankang (January 2022). "A narrative review of molecular mechanism and therapeutic effect of cannabidiol (CBD)". Basic & Clinical Pharmacology & Toxicology. 130 (4): 439–456. doi:10.1111/bcpt.13710. PMID 35083862.
  4. ↑ Collins, Arianna; Ramirez, Giovanni; Tesfatsion, Tesfay; Ray, Kyle P; Caudill, Scott; Cruces, Westley (March 2023). "Synthesis and Characterization of the Diastereomers of HHC and H4CBD". Natural Product Communications. 18 (3): 1934578X2311589. doi:10.1177/1934578x231158910.