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H2-CBD

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H2-CBD
Names
IUPAC name 2'-Isopropyl-5'-methyl-4-pentyl-1',2',3',4'-tetrahydro--2,6-diol or 2-(5-methyl-2-(prop-1-en-2-yl)cyclohexyl)-5-pentylbenzene-1,3-diol
Other names Hydrogenated CBD, HCBD, HCBD, DiHydroCBD, DiHydroCannabidiol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
InChI
  • 1,2-dihydro: InChI=1S/C21H32O2/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/h12-13,15,17-18,22-23H,2,5-11H2,1,3-4H3/t15?,17-,18+/m0/s1Key: CODIXLGYYWMJFS-XSRYCBBQSA-N
SMILES
  • 1,2-dihydro: CCCCCC1=CC(=C(C(=C1)O)2CC(CC2C(=C)C)C)O
Properties
Chemical formula C21H32O2
Molar mass 316.485 g·mol
Related compounds
Related compounds H4-CBD
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

H2CBD (diHydroCBD, partially hydrogenated CBD) are cannabinoids that were first synthesized by Alexander R. Todd in 1940 by catalytic hydrogenation of cannabidiol.

The term "H2CBD" can refer to two different chemical compounds that differ by the site of hydrogenation, either saturated on the cyclohexenyl ring (i.e. 1,2-dihydrocannabidiol using the older terpenoid numbering scheme) or saturated on the isopropenyl side group, which is known as 8,9-dihydrocannabidiol.

H2CBD, H4-CBD, and 8,9-dihydrocannabidiol have all been referred to as "hydrogenated CBD" which may cause confusion.

Pharmacology

In 2006, it was discovered that 8,9-dihydrocannabidiol binds very weakly to the CB1 receptor with a binding affinity higher than 1 μM, but has potential anti-inflammatory effects independent of its cannabinoid receptor action.

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.
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