H2-CBD

H2-CBD
Names
	IUPAC name 2'-Isopropyl-5'-methyl-4-pentyl-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-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)	1,2-dihydro: Interactive image;
ChEMBL	1,2-dihydro: ChEMBL5266282;
ChemSpider	1,2-dihydro: 9697362;
PubChem CID	1,2-dihydro: 11522575;
	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/s1 Key: CODIXLGYYWMJFS-XSRYCBBQSA-N;
	SMILES 1,2-dihydro: CCCCCC1=CC(=C(C(=C1)O)[C@@H]2CC(CC[C@H]2C(=C)C)C)O;
Properties
Chemical formula	C21H32O2
Molar mass	316.485 g·mol−1
Related compounds
Related compounds	H4-CBD
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

H2CBD (diHydroCBD, partially hydrogenated CBD) are cannabinoids that were first synthesized by Alexander R. Todd in 1940 by catalytic hydrogenation of cannabidiol.^[1]

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.^[2]

References

^ 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.
^ 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.

[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.

[1]

[2]

H2-CBD

Pharmacology

See also

References

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