7-Hydroxycannabidiol

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. Like its precursor CBD, it is not known to exhibit any psychoactive effects on the body and is known to counter the psychoactive effects of THC if it is present at the same time. This mode of action in 2015 was discovered to be at least contributing in part by being a non competitive negative allosteric modulator of the Cannabinoid receptor type 1.[5]

7-Hydroxycannabidiol
Identifiers
  • 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
UNII
ChEBI
Chemical and physical data
FormulaC21H30O3
Molar mass330.468 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)CO)O
  • 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


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 2023-08-01). PMID 33305718.{{cite journal}}: CS1 maint: DOI inactive as of August 2023 (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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