{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"ZELUXPWDPVXUEI-ZWKOTPCHSA-N","prefName":"7-hidroxicannabidiol","symbol":"7-OH-CBD","iupacName":"2-[(1R,6R)-3-(hydroxymethyl)-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol","aliases":["7-OH-CBD","7-hydroxy-CBD","7-OH-cannabidiol","7-hydroxy-cannabidiol"],"cas":"50725-17-2","pubchemCid":"11301963","chebiId":null,"smiles":"C=1(C(=CC(=CC1O)CCCCC)O)[C@H]2[C@](CCC(=C2)CO)([H])C(C)=C","molecularFormula":"C21H30O3","molecularWeight":330.21949481999997,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/11301963"}},"classification":{"family":"ecs_tool","familyLabel":"Modulador del ECS (investigación)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origen (herramienta de investigación)","summaryFr":"No existe ninguna vía biosintética vegetal: el 7-OH-CBD es un producto del metabolismo animal. Nace de la hidroxilación del carbono 7 del cannabidiol por los citocromos P450 hepáticos, principalmente el CYP2C19 y el CYP2C9, interviniendo el CYP3A4 sobre todo en otras posiciones de la molécula. El material de referencia empleado en el laboratorio se obtiene por oxidación selectiva del cannabidiol.","originNote":"El 7-OH-CBD no existe en la planta de cannabis. Aparece en el organismo tras la ingestión de cannabidiol, por oxidación hepática. Fuera del cuerpo, solo existe como patrón analítico preparado en el laboratorio a partir del cannabidiol, destinado a los laboratorios de dosificación y de investigación.","discovered":""},"pharmacology":{"summaryFr":"El 7-hidroxicannabidiol es el principal metabolito activo del cannabidiol. Su formación reposa sobre la hidroxilación del carbono 7 por los citocromos P450 hepáticos, encargándose el CYP2C19 y el CYP2C9 de lo esencial de esta etapa, antes de una oxidación ulterior en 7-COOH-CBD, desprovisto de actividad. Las autoridades de registro del cannabidiol farmacéutico consideran el 7-OH-CBD como metabolito activo a partir de los modelos animales de crisis convulsiva, donde se comporta como el cannabidiol mientras que el 7-COOH-CBD es allí inactivo. La exposición plasmática al 7-OH-CBD sigue siendo inferior a la del cannabidiol original, mientras que el 7-COOH-CBD alcanza con mucho las concentraciones más elevadas. En el plano mecanicista, la literatura es claramente más escasa que para el cannabidiol: no se publica para este compuesto ninguna afinidad medida en CB1 ni en CB2, y la hipótesis de una modulación alostérica negativa de CB1 procede de la literatura de patentes y de cálculos de acoplamiento, no de una farmacología funcional validada. Lo que está demostrado atañe al metabolismo: el 7-OH-CBD inhibe el CYP2A6 y el CYP2B6 a concentraciones pertinentes, lo que lo convierte en un actor posible de las interacciones medicamentosas atribuidas al cannabidiol. Faltan los datos humanos de efecto propio, ya que nadie ha administrado este metabolito solo a voluntarios.","receptorSummaryFr":"El 7-OH-CBD comparte el esqueleto del cannabidiol, pero su perfil de dianas sigue mal definido. No se ha publicado para este compuesto ninguna constante de afinidad medida en CB1 ni en CB2: la literatura de patentes lo presenta como un modulador alostérico negativo de CB1, a imagen del propio cannabidiol, y un estudio de acoplamiento molecular de 2025 lo sitúa en el bolsillo de CB1 con una energía calculada ligeramente más favorable que la del cannabidiol. Estos resultados son computacionales y no establecen una actividad funcional. Ningún dato sólido documenta TRPV1, GPR55, PPARγ o 5-HT1A para este metabolito en particular, ya que los trabajos disponibles versan sobre el cannabidiol original. La diana mejor documentada del 7-OH-CBD no es, por lo demás, un receptor sino una enzima: inhibe el CYP2A6, principal metabolizador de la nicotina, así como el CYP2B6, a concentraciones próximas a las alcanzadas en la clínica.","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":15,"reported":null,"confidence":"low"},{"target":"CB2","efficacy":"modulator","relativeActivity":10,"reported":null,"confidence":"low"},{"target":"CYP2A6 (enzyme)","efficacy":"antagonist","relativeActivity":70,"reported":"IC50,u 0,45 ± 0,18 µM pour la formation de cotinine sur microsomes hépatiques humains","confidence":"medium"}],"references":[{"label":"Beers JL, Fu D, Jackson KD. Cytochrome P450-Catalyzed Metabolism of Cannabidiol to the Active Metabolite 7-Hydroxy-Cannabidiol. Drug Metab Dispos. 2021;49(10):882-891.","pmid":null,"doi":null,"url":"https://dmd.aspetjournals.org/content/49/10/882"},{"label":"Inhibition of Nicotine Metabolism by Cannabidiol (CBD) and 7-Hydroxycannabidiol (7-OH-CBD). Chem Res Toxicol. 2023.","pmid":"36626330","doi":"10.1021/acs.chemrestox.2c00259","url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC9945182/"},{"label":"Zhang Q, Melchert PW, Markowitz JS. Pharmacokinetic Variability of Oral Cannabidiol and Its Major Metabolites after Short-Term High-Dose Exposure in Healthy Subjects. Med Cannabis Cannabinoids. 2024;7(1):1-9.","pmid":"38292071","doi":"10.1159/000535726","url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC10824522/"},{"label":"Metabolism of Cannabidiol in Respiratory-Associated Cells and HepG2-Derived Cells and Molecular Docking of Cannabidiol and Its Metabolites with CYP Enzymes and Cannabinoid Receptors. Int J Mol Sci. 2025;26:8384.","pmid":"40943305","doi":"10.3390/ijms26178384","url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC12428432/"},{"label":"Li Y, Li X, Wu Q, et al. 7-Hydroxycannabidiol and 7-carboxycannabidiol induced cytotoxicity via apoptosis and endoplasmic reticulum stress in human hepatic cells. Arch Toxicol. 2025;99:2627-2638.","pmid":null,"doi":null,"url":"https://link.springer.com/article/10.1007/s00204-025-04001-7"},{"label":"Wu Q, Fang JL, Nagumalli SK, Guo X, Beland FA. NAD(P)+-dependent alcohol oxidoreductases oxidize 7-hydroxycannabidiol to a reactive formyl metabolite. Arch Toxicol. 2025;99(11):4411-4421.","pmid":null,"doi":null,"url":"https://link.springer.com/article/10.1007/s00204-025-04140-x"},{"label":"FDA, EPIDIOLEX (cannabidiol) oral solution, prescribing information, section 12.3 Pharmacokinetics (metabolites 7-OH-CBD and 7-COOH-CBD).","pmid":null,"doi":null,"url":"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210365lbl.pdf"},{"label":"Agence européenne des médicaments, Epidyolex (cannabidiol), EPAR, autorisation de mise sur le marché du 19 septembre 2019.","pmid":null,"doi":null,"url":"https://www.ema.europa.eu/en/medicines/human/EPAR/epidyolex"},{"label":"Légifrance, arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants, annexe IV (tétrahydrocannabinols, leurs esters, éthers et sels).","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/loda/article_lc/LEGIARTI000020689963/2009-02-27"},{"label":"Ujváry I, Hanuš L. Human Metabolites of Cannabidiol: A Review on Their Formation, Biological Activity, and Relevance in Therapy. Cannabis Cannabinoid Res. 2016.","pmid":null,"doi":null,"url":"https://journals.sagepub.com/doi/full/10.1089/can.2015.0012"},{"label":"Nilsson I, Agurell S, Nilsson JL, Widman M, Leander K. Two cannabidiol metabolites formed by rat liver. J Pharm Pharmacol. 1973.","pmid":null,"doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/4146589/"},{"label":"Martin B, et al. Identification of monohydroxylated metabolites of cannabidiol formed by rat liver. J Pharm Pharmacol. 1976.","pmid":null,"doi":null,"url":"https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.1976.tb04152.x"},{"label":"Tchilibon S, Mechoulam R. Synthesis of a Primary Metabolite of Cannabidiol. Org Lett. 2000.","pmid":null,"doi":null,"url":"https://pubs.acs.org/doi/10.1021/ol006369a"},{"label":"In vitro effects of cannabidiol and its main metabolites in mouse and human Sertoli cells. Food Chem Toxicol. 2022.","pmid":null,"doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/34871667/"},{"label":"Automated Workflow for High-Throughput LC-MS/MS Therapeutic Monitoring of Cannabidiol and 7-Hydroxy-cannabidiol in Patients with Epilepsy. Int J Mol Sci. 2025.","pmid":null,"doi":null,"url":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12295711/"},{"label":"7-Hydroxycannabidiol, article de synthèse Wikipedia (identifiants et repères historiques).","pmid":null,"doi":null,"url":"https://en.wikipedia.org/wiki/7-Hydroxycannabidiol"}]},"pharmacokinetics":null,"metabolism":null,"detection":null,"subjectiveEffects":{"profile":[{"key":"calm","label":"Calma","description":"Relajación del cuerpo y de la mente; menos ruido mental, sin somnolencia marcada.","intensity":12},{"key":"focus","label":"Claridad","description":"Atención sostenida y pensamiento claro; lucidez funcional, sin euforia.","intensity":6},{"key":"sleep","label":"Sueño","description":"Efecto sedante: favorece la conciliación del sueño y la continuidad del sueño profundo.","intensity":8},{"key":"appetite","label":"Apetito","description":"Estimulación del hambre y de la apreciación gustativa (efecto «munchies»).","intensity":4},{"key":"uplift","label":"High","description":"Euforia e intensidad sensorial; percepción del tiempo y del espacio modificada.","intensity":4}],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":null},"legal":{"scheduleStatus":"unscheduled","scheduleLabel":"No listado","frScheduleStatus":"unscheduled","tiers":[{"jurisdiction":"international","jurisdictionLabel":"International","label":null,"reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"eu","jurisdictionLabel":"Union européenne","label":"Ningún Estado miembro somete el 7-OH-CBD a control como tal, y no figura ni en el sistema de alerta temprana de la EUDA ni en las listas de los convenios internacionales. El cannabidiol del que deriva no está sometido a fiscalización internacional, pero sí está regulado como sustancia activa de medicamento: la Agencia Europea de Medicamentos autorizó en 2019 una solución oral de cannabidiol para determinadas epilepsias raras. El 7-OH-CBD solo aparece en ese expediente como metabolito documentado, sin estatuto reglamentario propio.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"El 7-OH-CBD no está nombrado en ninguna decisión de clasificación de la ANSM. Tampoco lo capta la cláusula genérica del anexo IV del arrêté (orden ministerial) del 22 de febrero de 1990, que contempla los « tétrahydrocannabinols, leurs esters, éthers, sels ainsi que les sels des dérivés précités »: este metabolito deriva del cannabidiol y no de un tetrahidrocannabinol, y no es ni un éster ni un éter de este. Su estatuto es, por tanto, el de sustancia no clasificada. Su presencia en el organismo de una persona que consume cannabidiol no acarrea por sí misma ninguna consecuencia penal.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Beers JL, Fu D, Jackson KD. Cytochrome P450-Catalyzed Metabolism of Cannabidiol to the Active Metabolite 7-Hydroxy-Cannabidiol. Drug Metab Dispos. 2021;49(10):882-891.","pmid":null,"doi":null,"url":"https://dmd.aspetjournals.org/content/49/10/882"},{"label":"Inhibition of Nicotine Metabolism by Cannabidiol (CBD) and 7-Hydroxycannabidiol (7-OH-CBD). Chem Res Toxicol. 2023.","pmid":"36626330","doi":"10.1021/acs.chemrestox.2c00259","url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC9945182/"},{"label":"Zhang Q, Melchert PW, Markowitz JS. Pharmacokinetic Variability of Oral Cannabidiol and Its Major Metabolites after Short-Term High-Dose Exposure in Healthy Subjects. Med Cannabis Cannabinoids. 2024;7(1):1-9.","pmid":"38292071","doi":"10.1159/000535726","url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC10824522/"},{"label":"Metabolism of Cannabidiol in Respiratory-Associated Cells and HepG2-Derived Cells and Molecular Docking of Cannabidiol and Its Metabolites with CYP Enzymes and Cannabinoid Receptors. Int J Mol Sci. 2025;26:8384.","pmid":"40943305","doi":"10.3390/ijms26178384","url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC12428432/"},{"label":"Li Y, Li X, Wu Q, et al. 7-Hydroxycannabidiol and 7-carboxycannabidiol induced cytotoxicity via apoptosis and endoplasmic reticulum stress in human hepatic cells. Arch Toxicol. 2025;99:2627-2638.","pmid":null,"doi":null,"url":"https://link.springer.com/article/10.1007/s00204-025-04001-7"},{"label":"Wu Q, Fang JL, Nagumalli SK, Guo X, Beland FA. NAD(P)+-dependent alcohol oxidoreductases oxidize 7-hydroxycannabidiol to a reactive formyl metabolite. Arch Toxicol. 2025;99(11):4411-4421.","pmid":null,"doi":null,"url":"https://link.springer.com/article/10.1007/s00204-025-04140-x"},{"label":"FDA, EPIDIOLEX (cannabidiol) oral solution, prescribing information, section 12.3 Pharmacokinetics (metabolites 7-OH-CBD and 7-COOH-CBD).","pmid":null,"doi":null,"url":"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210365lbl.pdf"},{"label":"Agence européenne des médicaments, Epidyolex (cannabidiol), EPAR, autorisation de mise sur le marché du 19 septembre 2019.","pmid":null,"doi":null,"url":"https://www.ema.europa.eu/en/medicines/human/EPAR/epidyolex"},{"label":"Légifrance, arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants, annexe IV (tétrahydrocannabinols, leurs esters, éthers et sels).","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/loda/article_lc/LEGIARTI000020689963/2009-02-27"},{"label":"Ujváry I, Hanuš L. Human Metabolites of Cannabidiol: A Review on Their Formation, Biological Activity, and Relevance in Therapy. Cannabis Cannabinoid Res. 2016.","pmid":null,"doi":null,"url":"https://journals.sagepub.com/doi/full/10.1089/can.2015.0012"},{"label":"Nilsson I, Agurell S, Nilsson JL, Widman M, Leander K. Two cannabidiol metabolites formed by rat liver. J Pharm Pharmacol. 1973.","pmid":null,"doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/4146589/"},{"label":"Martin B, et al. Identification of monohydroxylated metabolites of cannabidiol formed by rat liver. J Pharm Pharmacol. 1976.","pmid":null,"doi":null,"url":"https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.1976.tb04152.x"},{"label":"Tchilibon S, Mechoulam R. Synthesis of a Primary Metabolite of Cannabidiol. Org Lett. 2000.","pmid":null,"doi":null,"url":"https://pubs.acs.org/doi/10.1021/ol006369a"},{"label":"In vitro effects of cannabidiol and its main metabolites in mouse and human Sertoli cells. Food Chem Toxicol. 2022.","pmid":null,"doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/34871667/"},{"label":"Automated Workflow for High-Throughput LC-MS/MS Therapeutic Monitoring of Cannabidiol and 7-Hydroxy-cannabidiol in Patients with Epilepsy. Int J Mol Sci. 2025.","pmid":null,"doi":null,"url":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12295711/"},{"label":"7-Hydroxycannabidiol, article de synthèse Wikipedia (identifiants et repères historiques).","pmid":null,"doi":null,"url":"https://en.wikipedia.org/wiki/7-Hydroxycannabidiol"}],"meta":{"slug":"7-oh-cbd","url":"https://es.phytogrammes.com/wiki/7-oh-cbd","lastVerified":"2026-05-01","dataUpdatedAt":"2026-07-29","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}