H4-CBD

H4CBD (Hydrogenated CBD, Tetrahydrocannibidiol), is a cannabinoid that was first synthesized by the Todd group in 1940 derived from the catalytic hydrogenation of cannabidiol.[1]

H4-CBD
Names
IUPAC name
2-(2-isopropyl-5-methylcyclohexyl)-5-pentylbenzene-1,3-diol
Other names
Hydrogenated CBD, HCBD, TetrahydroCannibidiol, 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).
Infobox references

It's important to note that H4CBD, and 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 145nM at the CB1 receptor and potential anti-inflammatory effects independent of its cannabinoid receptor action.[2] 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 nM[3]

Elucidation

In 2023 H4CBD epimers were elucidated using NOESY, COSY, NMR spectroscopic techniques, while the inclusion of LC-MS and SCFC were used to isolate individual diasteromers[4].

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. "A narrative review of molecular mechanism and therapeutic effect of cannabidiol (CBD)". Basic & Clinical Pharmacology & Toxicology. January 2022.
  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.
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