{"Abbreviation":"","Aliases":["7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole","Banisterine","Telepathine","Leucoharmine","Yageine","Yajeine","9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl-","7-Methoxy-1-methyl-9H-β-carboline","Banisterin","Telepathin"],"CAS":"442-51-3","ChEBI":"CHEBI:28121","ChEMBL":"CHEMBL269538","ChemicalClasses":["β-carboline"],"Chirality":"achiral","Classes":["Monoamine oxidase inhibitor"],"Dosing Info":[],"DrugClasses":[],"EINECS":"207-131-4","European Community (EC) Number":"207-131-4","FullSalts":["Harmine hydrochloride"],"HMDB ID":"HMDB0030311","HeavyAtomCount":16,"IUPACName":"7-methoxy-1-methyl-9H-pyrido[3,4-b]indole","InChI":"InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3","InChIKey":"BXNJHAXVSOCGBA-UHFFFAOYSA-N","MeSH Pharmacological Classification":"A chemically heterogeneous group of drugs that have in common the ability to block oxidative deamination of naturally occurring monoamines. (From Gilman, et al., Goodman and Gilman\u0026apos;s The Pharmacological Basis of Therapeutics, 8th ed, p414) (See all compounds classified as Monoamine Oxidase Inhibitors.)","Melting Point":"264 - 265 °C","MolecularFormula":"C\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO","MolecularWeight":"212.25 g/mol","Physical Description":"Solid","PrevSalts":["hydrochloride"],"PubChemId":5280953,"Record Description":["Harmine is a harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7. It has a role as a metabolite, an anti-HIV agent and an EC 1.4.3.4 (monoamine oxidase) inhibitor. It derives from a hydride of a harman.","Harmine has been reported in Passiflora phoenicia, Symplocos setchuensis, and other organisms with data available.","HARMINE is a small molecule drug with a maximum clinical trial phase of I and has 1 investigational indication.","Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.","Harmine is a harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7. It has a role as a metabolite, an anti-HIV agent and an EC 1.4.3.4 (monoamine oxidase) inhibitor. It derives from a hydride of a harman.","Wikipedia|TiHKAL|Tryptamines"],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Harmine","Name":"Harmine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q128381","Name":"Harmine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB07919","Name":"Harmine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5280953","Name":"Harmine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL269538","Name":"Harmine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28121","Name":"Harmine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=442-51-3","Name":"Harmine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0030311","Name":"Harmine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C06538","Name":"Harmine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/4FHH5G48T7","Name":"Harmine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID30196066","Name":"Harmine","Sub":false}]}],"SMILES":"CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC","Salts":["hydrochloride"],"SaltsAcidCount":[1],"SaltsAmineCount":[1],"SaltsUNII":["T89I34ODAA"],"StoreUNII":["4FHH5G48T7"],"StructureBase64":"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