{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"CYQFCXCEBYINGO-IAGOWNOFSA-N","prefName":"Delta-9-tetrahidrocannabinol","symbol":"Δ9-THC","iupacName":"(6aR,10aR)-6,6,9-triméthyl-3-pentyl-6a,7,8,10a-tétrahydro-6H-benzo[c]chromén-1-ol","aliases":["THC","Delta-9-THC","Dronabinol (DCI)"],"cas":"1972-08-3","pubchemCid":"16078","chebiId":"66964","smiles":"CCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O","molecularFormula":"C21H30O2","molecularWeight":314.46,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/16078","chebi":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66964"}},"classification":{"family":"principal","familyLabel":"Fitocannabinoide mayor","origin":"natural","originLabel":"Naturel","structuralClassFr":null},"originSynthesis":{"heading":"Vía biosintética","summaryFr":"Descarboxilación térmica del THCA, producido a su vez a partir del CBGA mediante la THCA-sintasa","originNote":"Planta","discovered":"1964"},"pharmacology":{"summaryFr":"El cannabinoide de referencia - el que permitió a Raphael Mechoulam y Yehiel Gaoni sentar, en 1964 (J. Am. Chem. Soc. 86:1646), los cimientos de toda la farmacología cannábica moderna. Agonista parcial CB1 (Ki = 40,7 nM, Emax ≈ 40 %) y CB2 (Ki = 36 nM) - es sobre este perfil sobre el que se ha calcado toda la química de los cannabinoides sintéticos. Metabolizado por CYP2C9 / CYP3A4 / CYP2C19 en 11-OH-Δ9-THC (metabolito activo, más potente que el parental) y luego en 11-COOH-Δ9-THC (inactivo, el marcador urinario). Biodisponibilidad oral de solo 4–12 %, con una gran variabilidad interindividual; en torno al 30 % por inhalación. Semivida terminal de 20–30 h. En el plano terapéutico, el THC sintético se comercializa bajo el nombre de dronabinol (Marinol/Syndros, FDA 1985) para las náuseas inducidas por quimioterapia y la anorexia ligada al VIH; el Sativex (nabiximoles, THC + CBD 1:1) está autorizado en el Reino Unido desde 2010 para la espasticidad de la EM. Para Phytogrammes, el Δ9-THC nunca supera 0,3 % de la masa total del producto acabado, conforme al reglamento (UE) 2021/2115 (artículo 4, en vigor desde el 1 de enero de 2023) y a la decisión del Conseil d'État del 29 de diciembre de 2022 - es ese umbral el que hace que nuestras flores y resinas sean vendibles en Francia y en otros 26 países de la UE.","receptorSummaryFr":"Agonista parcial CB1 (Ki ≈ 40,7 nM, Emax ≈ 40 %) y CB2 (Ki ≈ 36 nM)","binding":[{"target":"CB1","efficacy":"partial_agonist","relativeActivity":90,"reported":"Ki = 40,7 nM · Emax ≈ 40 %","confidence":"medium"},{"target":"CB2","efficacy":"partial_agonist","relativeActivity":70,"reported":"Ki = 36 nM","confidence":"medium"},{"target":"GPR55","efficacy":"full_agonist","relativeActivity":40,"reported":"agoniste faible · µM range","confidence":"medium"},{"target":"TRPV2","efficacy":"full_agonist","relativeActivity":50,"reported":"agoniste · activation thermique","confidence":"medium"},{"target":"PPARγ","efficacy":"modulator","relativeActivity":35,"reported":"agoniste partiel","confidence":"medium"}],"references":[{"label":"Pertwee - BJP 2008 · récepteurs CB1/CB2","pmid":"17828291","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/17828291/"},{"label":"Huestis - PK orale 4–12 %","pmid":"16237477","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/16237477/"},{"label":"Gaoni & Mechoulam - JACS 1964","pmid":null,"doi":"10.1021/ja01062a046","url":"https://doi.org/10.1021/ja01062a046"}]},"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":50},{"key":"focus","label":"Claridad","description":"Atención sostenida y pensamiento claro; lucidez funcional, sin euforia.","intensity":30},{"key":"sleep","label":"Sueño","description":"Efecto sedante: favorece la conciliación del sueño y la continuidad del sueño profundo.","intensity":65},{"key":"appetite","label":"Apetito","description":"Estimulación del hambre y de la apreciación gustativa (efecto «munchies»).","intensity":85},{"key":"uplift","label":"High","description":"Euforia e intensidad sensorial; percepción del tiempo y del espacio modificada.","intensity":95}],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[{"brand":"Marinol / Syndros (dronabinol)","context":""},{"brand":"Sativex (nabiximols)","context":""}]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":null},"legal":{"scheduleStatus":"controlled-named","scheduleLabel":"Estupefaciente: listado nominalmente","frScheduleStatus":null,"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":"Convenio de 1971 · Anexo II: umbral en producto acabado 0,3 %","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Estupefaciente: arrêté (orden ministerial) del 22 de febrero de 1990","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Pertwee - BJP 2008 · récepteurs CB1/CB2","pmid":"17828291","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/17828291/"},{"label":"Huestis - PK orale 4–12 %","pmid":"16237477","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/16237477/"},{"label":"Gaoni & Mechoulam - JACS 1964","pmid":null,"doi":"10.1021/ja01062a046","url":"https://doi.org/10.1021/ja01062a046"}],"meta":{"slug":"thc","url":"https://es.phytogrammes.com/wiki/thc","lastVerified":"2026-05-01","dataUpdatedAt":"2026-05-01","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}