7-Hydroxycannabidiol

7-Hydroxycannabidiol
Identifiers
IUPAC name
  • 2-[(1R,6R)-3-(Hydroxymethyl)-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
CAS Number
PubChem CID
ChemSpider
ChEBI
Chemical and physical data
FormulaC21H30O3
Molar mass330.468 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)CO)O
InChI
  • InChI=1S/C21H30O3/c1-4-5-6-7-15-11-19(23)21(20(24)12-15)18-10-16(13-22)8-9-17(18)14(2)3/h10-12,17-18,22-24H,2,4-9,13H2,1,3H3/t17-,18+/m0/s1
  • Key:ZELUXPWDPVXUEI-ZWKOTPCHSA-N

7-Hydroxycannabidiol (7-OH-CBD) is an active metabolite of cannabidiol, generated in the body from cannabidiol by the action of the enzyme CYP2C19.[1] While methods have been developed for its synthetic production,[2] and measurement of levels in the body following consumption of cannabidiol,[3] its pharmacology has been relatively little studied, though it has been found to possess similar anticonvulsant effects to cannabidiol itself,[4] as well as lowering blood triglyceride levels.[5]


See also

References

  1. ↑ Vlad RA, Hancu G, Ciurba A, Antonoaea P, Rédai EM, Todoran N, Silasi O, Muntean DL (October 2020). "Cannabidiol - therapeutic and legal aspects". Die Pharmazie. 75 (10): 463–469. doi:10.1691/ph.2020.0076 (inactive 31 October 2021). PMID 33305718.{{cite journal}}: CS1 maint: DOI inactive as of October 2021 (link)
  2. ↑ Tchilibon S, Mechoulam R (October 2000). "Synthesis of a primary metabolite of cannabidiol". Organic Letters. 2 (21): 3301–3. doi:10.1021/ol006369a. PMID 11029195.
  3. ↑ Pérez-Acevedo AP, Busardò FP, Pacifici R, Mannocchi G, Gottardi M, Poyatos L, Papaseit E, Pérez-Mañá C, Martin S, Di Trana A, Pichini S, Farré M (December 2020). "Disposition of Cannabidiol Metabolites in Serum and Urine from Healthy Individuals Treated with Pharmaceutical Preparations of Medical Cannabis". Pharmaceuticals (Basel, Switzerland). 13 (12): 459. doi:10.3390/ph13120459. PMC 7763054. PMID 33322849.
  4. ↑ WO 2015198078, Colin S, Nick Jones N, Whalley B, Stephens G, Williams C, "7-hydroxy-cannabidiol (7-OH-CBD) and/or 7-oh-cannabidivarin (7-OH-CBDV) for use in the treatment of epilepsy.", published 30 December 2015, assigned to GW Pharma Limited
  5. ↑ WO 2015198077, Stott C, Duncan M, Di Marzo V, Silverstri C, Martella A, "7-Hydroxy cannabidiol (7-OH-CBD) for use in the treatment of non-alcoholic fatty liver disease (NAFLD)", published 30 December 2015, assigned to GW Pharma Limited
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