H4-CBD

H4-CBD

H4-CBD

Chemical compound

H4CBD (hydrogenated CBD, tetrahydrocannabidiol) is a cannabinoid that was first synthesized by Alexander R. Todd in 1940 derived from the catalytic hydrogenation of cannabidiol.[1]

Quick Facts Names, Identifiers ...

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.[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 mM.[3]

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.[4]

See also

References

  1. [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. [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. [3]
    "A narrative review of molecular mechanism and therapeutic effect of cannabidiol (CBD)". Basic & Clinical Pharmacology & Toxicology. January 2022.
  4. [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.
Share this article:

This article uses material from the Wikipedia article H4-CBD, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.