Cannabidiol dimethyl ether

Cannabidiol dimethyl ether (CBDD) is a trace component of cannabis which can also be made synthetically. It is a potent and selective inhibitor of the enzyme 15-lipoxygenase and inhibits oxygenation of linoleic acid, a process involved in the development of atherosclerosis.[1][2]

Cannabidiol dimethyl ether
Identifiers
IUPAC name
  • 1,3-dimethoxy-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H34O2
Molar mass342.523 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCC1=CC(=C(C(=C1)OC)[C@@H]2C=C(CC[C@H]2C(=C)C)C)OC
InChI
  • InChI=1S/C23H34O2/c1-7-8-9-10-18-14-21(24-5)23(22(15-18)25-6)20-13-17(4)11-12-19(20)16(2)3/h13-15,19-20H,2,7-12H2,1,3-6H3/t19-,20+/m0/s1
  • Key:UYBGHBAVRNATET-VQTJNVASSA-N

See also

References
  1. Takeda S, Usami N, Yamamoto I, Watanabe K (August 2009). "Cannabidiol-2',6'-dimethyl ether, a cannabidiol derivative, is a highly potent and selective 15-lipoxygenase inhibitor". Drug Metabolism and Disposition. 37 (8): 1733–7. doi:10.1124/dmd.109.026930. PMID 19406952.
  2. Takeda S, Hirayama A, Urata S, Mano N, Fukagawa K, Imamura M, et al. "Cannabidiol-2',6'-dimethyl ether as an effective protector of 15-lipoxygenase-mediated low-density lipoprotein oxidation in vitro". Biological & Pharmaceutical Bulletin. 34 (8): 1252–6. doi:10.1248/bpb.34.1252. PMID 21804214.
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