{"ATC Code":"A - Alimentary tract and metabolism","Abbreviation":"THC","Aliases":["Dronabinol","Tetrahydrocannabinol","Δ9-Tetrahydrocannabinol","Δ9-THC","Δnyne","Abbott 40566","Δ-9-THC","Δ(9)-THC","Dronabinolum","Δ1-THC"],"Biological Half-Life":"The elimination phase of dronabinol can be described using a two-compartment model with an initial (alpha) half-life of about 4 hours and a terminal (beta) half-life of 25 to 36 hours.","Boiling Point":"392 °","CAS":"1972-08-3","ChEBI":"CHEBI:66964","ChEMBL":"CHEMBL465","ChemicalClasses":["benzochromene"],"Chirality":"absolute","Color/Form":"Light yellow resinous oil","DEA no":7369,"Decomposition":"When heated to decomposition it emits acrid smoke and irritating fumes.","Dosing Info":[],"Drug Classes":"Breast Feeding; Lactation; Milk, Human; Antiemetics; Cannabinoids","Drug Indication":"Dronabinol is indicated for the treatment of anorexia associated with weight loss in patients with AIDS, and nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments.","Drug Warnings":"Dronabinol capsules are contraindicated in any patient who has a known sensitivity to dronabinol or any of its ingredients. It contains cannabinoid and sesame oil and should never be used by patients allergic to these substances.","DrugClasses":["cannabinoid","hallucinogens","stimulant"],"DurationOfAction":"","EliminationHalfLife":"1.6–59 h, 25–36 h (orally administered dronabinol)","European Community (EC) Number":"625-153-6","FDA Pharmacological Classification":"7J8897W37S","HMDB ID":"HMDB0014613","HMDB Metabolite":[{"average_molecular_weight":314.4617,"biospecimens":["Blood","Urine"],"cas_registry_number":"1972-08-3","chebi_id":"66964","chemical_formula":"C21H30O2","chemspider_id":"15266","direct_substituent":"2,2-dimethyl-1-benzopyrans","drugbank_id":"DB00470","inchi":"InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1","inchikey":"CYQFCXCEBYINGO-IAGOWNOFSA-N","iupac_name":"(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol","kegg_id":"C06972","name":"Tetrahydrocannabinol","pdb_id":"","proteins":[{"gene_name":"PTGS1","name":"Prostaglandin G/H synthase 1","protein_accession":"HMDBP00976","protein_type":"Unknown","uniprot_id":"P23219"},{"gene_name":"CYP3A4","name":"Cytochrome P450 3A4","protein_accession":"HMDBP01018","protein_type":"Unknown","uniprot_id":"P08684"},{"gene_name":"CYP2C9","name":"Cytochrome P450 2C9","protein_accession":"HMDBP01036","protein_type":"Unknown","uniprot_id":"P11712"},{"gene_name":"CYP2C19","name":"Cytochrome P450 2C19","protein_accession":"HMDBP01038","protein_type":"Unknown","uniprot_id":"P33261"},{"gene_name":"CYP1A1","name":"Cytochrome P450 1A1","protein_accession":"HMDBP01555","protein_type":"Unknown","uniprot_id":"P04798"},{"gene_name":"CYP2A6","name":"Cytochrome P450 2A6","protein_accession":"HMDBP01567","protein_type":"Unknown","uniprot_id":"P11509"},{"gene_name":"ABCB1","name":"Multidrug resistance protein 1","protein_accession":"HMDBP02101","protein_type":"Transporter","uniprot_id":"P08183"},{"gene_name":"ABCG2","name":"ATP-binding cassette sub-family G member 2","protein_accession":"HMDBP02257","protein_type":"Transporter","uniprot_id":"Q9UNQ0"},{"gene_name":"CNR1","name":"Cannabinoid receptor 1","protein_accession":"HMDBP10803","protein_type":"Unknown","uniprot_id":"P21554"}],"pubchem_compound_id":"16078","smiles":"[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21","substituents":["1-hydroxy-2-unsubstituted benzenoid","1-hydroxy-4-unsubstituted benzenoid","2,2-dimethyl-1-benzopyran","Alkyl aryl ether","Aromatic heteropolycyclic compound","Benzenoid","Ether","Hydrocarbon derivative","Organic oxygen compound","Organooxygen compound","Oxacycle"],"synonyms":["(-)-delta9-trans-Tetrahydrocannabinol","1-trans-delta-9-Tetrahydrocannabinol","3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,D)pyran-1-ol","6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol","Delta(1)-Tetrahydrocannabinol","delta9-Tetrahydrocannabinol","Delta(9)-THC","Dronabinol","Dronabinolum","Syndros","THC","Marinol","(-)-Δ9-trans-tetrahydrocannabinol","1-trans-Δ-9-tetrahydrocannabinol","Δ(1)-tetrahydrocannabinol","Δ9-tetrahydrocannabinol","Δ(9)-THC","DELTA-9-THC","DELTA-9-TETRAHYDROCANNABINOL","Δ-9-THC","Δ-9-tetrahydrocannabinol","Tetrahydrocannabinol, (6a-trans)-isomer","9-Ene-tetrahydrocannabinol","Tetrahydrocannabinol, (6ar-cis)-isomer","Tetrahydrocannabinol, (6as-cis)-isomer","Tetrahydrocannabinol, trans isomer","delta(9)-Tetrahydrocannabinol","delta(1)-THC","9 Ene tetrahydrocannabinol","Solvay brand OF tetrahydrocannabinol","Tetrahydrocannabinol, trans-(+-)-isomer","Tetrahydrocannabinol, trans-isomer","delta 1-Tetrahydrocannabinol","(-)- delta 9-Tetrahydrocannabinol","(-)-delta 1-Tetrahydrocannabinol","(-)-delta 9-THC","(-)-delta 9-trans-Tetrahydrocannabinol","(-)-trans-delta 1-Tetrahydrocannabinol","(-)-trans-delta 9-Tetrahydrocannabinol","(-)-trans-delta 9-THC","(L)-delta 1-Tetrahydrocannabinol","1-trans-delta 9-Tetrahydrocannabinol","14C-delta 1-Tetrahydrocannabinol","delta 1-THC","delta 9-Tetrahydrocannabinol","delta 9-THC","delta 9-trans-Tetrahydrocannabinol","Exocyclic delta (9)(11)-tetrahydrocannabiol","L-delta 1-trans-Tetrahydrocannabinol","L-trans-delta 9-Tetrahydrocannabinol","Primolut","trans-delta (-)-9-Tetrahydrocannabinol","trans-delta 9-Tetrahydrocannabinol","Tetrahydrocannabinol","(-)-3,4-trans-delta1-Tetrahydrocannabinol","(-)-3,4-trans-Δ1-Tetrahydrocannabinol","(-)-delta1-Tetrahydrocannabinol","(-)-delta9-THC","(-)-delta9-Tetrahydrocannabinol","(-)-trans-delta1-Tetrahydrocannabinol","(-)-trans-delta9-THC","(-)-trans-delta9-Tetrahydrocannabinol","(-)-trans-Δ1-Tetrahydrocannabinol","(-)-trans-Δ9-THC","(-)-trans-Δ9-Tetrahydrocannabinol","(-)-Δ1-Tetrahydrocannabinol","(-)-Δ9-THC","(-)-Δ9-Tetrahydrocannabinol","(l)-delta1-Tetrahydrocannabinol","(l)-Δ1-Tetrahydrocannabinol","delta1-THC","delta1-Tetrahydrocannabinol","delta9-THC","delta9-trans-Tetrahydrocannabinol","l-delta1-trans-Tetrahydrocannabinol","l-trans-delta9-Tetrahydrocannabinol","l-trans-Δ9-Tetrahydrocannabinol","l-Δ1-trans-Tetrahydrocannabinol","trans-(-)-delta9-Tetrahydrocannabinol","trans-(-)-Δ9-Tetrahydrocannabinol","trans-delta9-Tetrahydrocannabinol","trans-Δ9-Tetrahydrocannabinol","Δ1-THC","Δ1-Tetrahydrocannabinol","Δ9-THC","Δ9-trans-Tetrahydrocannabinol"],"tissue":[],"wikipedia_id":"Tetrahydrocannabinol"}],"HeavyAtomCount":23,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Antiemetics; Cannabinoids","IUPACName":"(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol","Impurities":["exo-tetrahydrocannabinol","cannabinol","delta-8-tetrahydrocannabinol"],"InChI":"InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1","InChIKey":"CYQFCXCEBYINGO-IAGOWNOFSA-N","MeSH Pharmacological Classification":"Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise. (See all compounds classified as Hallucinogens.)","Melting Point":"200 °C","MolecularFormula":"C\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"314.5 g/mol","Opticalactivity":"UNSPECIFIED","Pharmacodynamics":"Dronabinol-induced sympathomimetic activity may result in tachycardia and/or conjunctival injection. Its effects on blood pressure are inconsistent, but subjects have experienced orthostatic hypotension and/or syncope upon abrupt standing.  Dronabinol also demonstrates reversible effects on appetite, mood, cognition, memory, and perception. These phenomena appear to be dose-related, increasing in frequency with higher dosages, and subject to great inter-patient variability. After oral administration, dronabinol capsules have an onset of action of approximately 0.5 to 1 hour and a peak effect at 2 to 4 hours. Duration of action for psychoactive effects is 4 to 6 hours, but the appetite stimulant effect of dronabinol may continue for 24 hours or longer after administration.  Tachyphylaxis and tolerance develop to some of the cardiovascular and CNS pharmacologic effects of dronabinol with chronic use, suggesting an indirect effect on sympathetic neurons. In a study of the pharmacodynamics of chronic dronabinol exposure, healthy male subjects (N = 12) received 12 times the maximum dose for anorexia associated with weight loss in patients with AIDS of dronabinol capsules in divided doses for 16 days. An initial tachycardia induced by dronabinol was replaced successively by normal sinus rhythm and then bradycardia. A decrease in supine blood pressure, made worse by standing, was also observed initially. These subjects developed tolerance to the cardiovascular and subjective adverse CNS effects of dronabinol within 12 days of treatment initiation.   Tachyphylaxis and tolerance do not appear to develop to the appetite stimulant effect of dronabinol. In clinical studies of dronabinol capsules in AIDS patients, at the recommended dosage, the appetite stimulant effect was sustained for up to five months.","Physical Description":"1-trans-delta-9-tetrahydrocannabinol appears as brown amorphous semi-solid, viscous oil or chunky golden yellow solid. (NTP, 1992)","PrevSalts":[],"PubChemId":16078,"Record Description":["delta-9-Tetrahydrocannabinol (Δ9-THC) can cause developmental toxicity according to an independent committee of scientific and health experts.","1-trans-delta-9-tetrahydrocannabinol appears as brown amorphous semi-solid, viscous oil or chunky golden yellow solid. (NTP, 1992)","Delta(9)-tetrahydrocannabinol is a diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy. It has a role as a metabolite, a non-narcotic analgesic, a hallucinogen, a cannabinoid receptor agonist and an epitope. It is a diterpenoid, a benzochromene, a polyketide and a phytocannabinoid.","Dronabinol is a DEA Schedule II controlled substance. Substances in the DEA Schedule II have a high potential for abuse which may lead to severe psychological or physical dependence. It is a Hallucinogenic substances substance.","Dronabinol (marketed as Marinol) is a synthetic form of delta-9-tetrahydrocannabinol (Δ⁹-THC), the primary psychoactive component of cannabis (marijuana). THC demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, which results in the well-known effects of smoking cannabis such as increased appetite, reduced pain, and changes in emotional and cognitive processes. Due to its evidence as an appetite stimulant and an anti-nauseant, Dronabinol is approved for use in anorexia associated with weight loss in patients with AIDS and for the treatment of nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments.  Tetrahydrocannabinol (THC) and cannabidiol (CBD) are the two most abundant cannabinoids found naturally in the resin of the marijuana plant, both of which are pharmacologically active due to their interaction with cannabinoid receptors that are found throughout the body. While both CBD and THC are used for medicinal purposes, they have different receptor activity, function, and physiological effects. If not provided in their activated form (such as through synthetic forms like Dronabinol or [DB00486]), THC and CBD are obtained through conversion from their precursors, tetrahydrocannabinolic acid-A (THCA-A) and cannabidiolic acid (CBDA), through decarboxylation reactions. This can be achieved through heating, smoking, vaporization, or baking of dried unfertilized female cannabis flowers.  From a pharmacological perspective, Cannabis' diverse receptor profile explains its potential application for such a wide variety of medical conditions. Cannabis contains more than 400 different chemical compounds, of which 61 are considered cannabinoids, a class of compounds that act upon endogenous cannabinoid receptors of the body. The endocannabinoid system is widely distributed throughout the central and peripheral nervous system (via the Cannabinoid Receptors CB1 and CB2) and plays a role in many physiological processes such as inflammation, cardiovascular function, learning, pain, memory, stress and emotional regulation, and the sleep/wake cycle among many others. CB1 receptors are found in both the central and peripheral nervous system, and are most abundant in the hippocampus and amygdala, which are the areas of the brain responsible for short-term memory storage and emotional regulation. CB2 receptors are mainly located in the peripheral nervous system and can be found on lymphoid tissue where they are involved in regulation of immune function.","Dronabinol is a Cannabinoid.","Dronabinol is an orally available cannabinoid agonist that is used to treat nausea and vomiting and to stimulate appetite, particularly in patients with wasting disease or cachexia. Dronabinol is associated with a minimal rate of serum enzyme elevations during therapy and has not been linked to cases of clinically apparent liver injury with jaundice.","Dronabinol has been reported in Cannabis sativa with data available.","Dronabinol is an isomer of tetrahydrocannabinol (THC) that is the main and most active isomer found in the Cannabis sativa L. plant, with potential anti-emetic, analgesic and appetite stimulating activities. Upon administration, dronabinol, also called delta-9-THC, targets and binds to cannabinoid receptors (CBRs) located in the central nervous system (CNS). Dronabinol acts directly on the appetite and vomiting control centers in the brain to stimulate appetite and prevent emesis. In addition, this agent induces analgesia. Urine levels may be used as a marker to determine the exposure to certain preparations containing parts of the cannabis plant, such as marijuana.","DRONABINOL is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1985 and has 5 approved and 31 investigational indications.","A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound. Dronabinol is a synthetic form of delta-9-THC. THC has a very low solubility in water, but good solubility in most organic solvents, specifically lipids and alcohols. There has never been a documented human fatality solely from overdosing on tetrahydrocannabinol or cannabis in its natural form. However, numerous reports have suggested an association of cannabis smoking with an increased risk of myocardial infarction.","A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.","delta-9-Tetrahydrocannabinol (Δ9-THC) can cause developmental toxicity according to an independent committee of scientific and health experts.","Delta(9)-tetrahydrocannabinol is a diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy. It has a role as a metabolite, a non-narcotic analgesic, a hallucinogen, a cannabinoid receptor agonist and an epitope. It is a diterpenoid, a benzochromene, a polyketide and a phytocannabinoid.","LiverTox|Gastroinestinal|Antiemetic|Cannabinoid"],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Tetrahydrocannabinol","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q190067","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00470","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/16078","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL465","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66964","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=1972-08-3","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014613","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D00306","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/7J8897W37S","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID6021327","Name":"Δ-9-tetrahydrocannabinol","Sub":false}]}],"Reported Fatal Dose":"The estimated lethal human dose of intravenous dronabinol is 30 mg/kg (2100 mg/70 kg).","SMILES":"CCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O","Scheduling":[{"gov":"Brazil","schedule":"Dronabinol: A3; THC \u003c30mg/ml: A3; others: F2 (prohibited). substance"},{"gov":"Canada","schedule":"Unscheduled substance"},{"gov":"Germany","schedule":"Dronabinol: II, other isomers and their stereochemical variants: I. substance"},{"gov":"United Kingdom","schedule":"Class B substance"},{"act":"Convention on Psychotropic Substances 1971","gov":"United Nations","schedule":"Schedule I drug"}],"Solubility":"2.8 mg/L at 73 °F (NTP, 1992)","Stability/Shelf Life":"Readily degraded in acid solutions.","StoreUNII":["7J8897W37S"],"Therapeutic Uses":"Hallucinogens Psychotropic Drugs Analgesics, Non-Narcotic Cannabinoid Receptor Agonists","Title":"Δ-9-tetrahydrocannabinol","UNII":"7J8897W37S","Wikidata":"Q190067","Wikipedia":"Tetrahydrocannabinol","XLogP":7}