7-Hydroxycannabidiol

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 2-[(1R,6R)-3-(Hydroxymethyl)-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

| image = 7-Hydroxycannabidiol_structure.png

| image_class = skin-invert-image

| width = 220

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 50725-17-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = N38G7JB3K2

| PubChem = 11301963

| ChemSpiderID = 9476939

| ChEMBL =

| ChEBI = 133053

| C=21 | H=30 | O=3

| smiles = CCCCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)CO)O

| StdInChI = 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

| StdInChIKey = 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.{{cite journal | vauthors = Vlad RA, Hancu G, Ciurba A, Antonoaea P, Rédai EM, Todoran N, Silasi O, Muntean DL | title = Cannabidiol - therapeutic and legal aspects | journal = Die Pharmazie | volume = 75 | issue = 10 | pages = 463–469 | date = October 2020 | pmid = 33305718 | doi = 10.1691/ph.2020.0076 | doi-broken-date = 1 November 2024 }} While methods have been developed for its synthetic production,{{cite journal | vauthors = Tchilibon S, Mechoulam R | title = Synthesis of a primary metabolite of cannabidiol | journal = Organic Letters | volume = 2 | issue = 21 | pages = 3301–3 | date = October 2000 | pmid = 11029195 | doi = 10.1021/ol006369a }} and measurement of levels in the body following consumption of cannabidiol,{{cite journal | vauthors = 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 | title = Disposition of Cannabidiol Metabolites in Serum and Urine from Healthy Individuals Treated with Pharmaceutical Preparations of Medical Cannabis | journal = Pharmaceuticals (Basel, Switzerland) | volume = 13 | issue = 12 | date = December 2020 | page = 459 | pmid = 33322849 | pmc = 7763054 | doi = 10.3390/ph13120459 | doi-access = free }} its pharmacology has been relatively little studied, though it has been found to possess similar anticonvulsant effects to cannabidiol itself,{{cite patent | country = WO | number = 2015198078 | title = 7-hydroxy-cannabidiol (7-OH-CBD) and/or 7-oh-cannabidivarin (7-OH-CBDV) for use in the treatment of epilepsy. | inventor = Colin S, Nick Jones N, Whalley B, Stephens G, Williams C | assign1 = GW Pharma Limited | pubdate = 30 December 2015 }} 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.{{cite patent | country = WO | number = 2015198077 | pubdate = 30 December 2015 | title = 7-Hydroxy cannabidiol (7-OH-CBD) for use in the treatment of non-alcoholic fatty liver disease (NAFLD) | inventor = Stott C, Duncan M, Di Marzo V, Silverstri C, Martella A | assign1 = GW Pharma Limited }}