{"Abbreviation":"","Aliases":["Dihydroharmine","Harmidine","Armalin","3,4-Dihydroharmine","Harmalol methyl ether","O-Methylharmalol","Harmine, dihydro-","3H-Pyrido[3,4-b]indole, 4,9-dihydro-7-methoxy-1-methyl-","harmalin","1-Methyl-7-methoxy-3,4-dihydro-beta-carboline"],"CAS":"304-21-2","ChEBI":"CHEBI:28172","ChEMBL":"CHEMBL340807","ChemicalClasses":["beta-carboline"],"Chirality":"achiral","Color/Form":"Orthorhombic bipyramidal prisms, tablets from methanol, rhombic octahedra from ethanol","DrugClasses":["stimulant"],"EINECS":"206-152-6","European Community (EC) Number":"206-152-6","Human Drugs":"Pharmaceuticals","IUPACName":"7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole","InChI":"InChI=1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3","InChIKey":"RERZNCLIYCABFS-UHFFFAOYSA-N","MeSH Pharmacological Classification":"A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here. (See all compounds classified as Central Nervous System Stimulants.)","Melting Point":"229-231 °C","MolecularFormula":"C\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO","MolecularWeight":"214.26 g/mol","PD":"PD056221","Physical Description":"Solid","PubChemId":3564,"Record Description":["Harmaline is a harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond. It has a role as a oneirogen. It derives from a hydride of a harman.","Harmaline has been reported in Passiflora phoenicia, Daphnia pulex, and other organisms with data available.","A beta-carboline alkaloid isolated from seeds of PEGANUM.","Harmaline is a harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond. It has a role as a oneirogen. It derives from a hydride of a harman.","Wikipedia|TiHKAL|Tryptamines"],"References":[{"name":"Wikipedia","url":"https://en.wikipedia.org/wiki/Harmaline"},{"name":"Wikidata","url":"https://www.wikidata.org/wiki/Q104252234"},{"name":"DrugBank","url":"https://go.drugbank.com/drugs/DB13875"},{"name":"PubChem","url":"https://pubchem.ncbi.nlm.nih.gov/compound/3564"},{"name":"ChemSpider","url":"https://www.chemspider.com/Chemical-Structure.4444444.html"},{"name":"ChEMBL","url":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL340807"},{"name":"ChEBI","url":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28172"},{"name":"Probes \u0026 Drugs","url":"https://www.probes-drugs.org/compound/PD056221"},{"name":"Common Chemistry","url":"https://commonchemistry.cas.org/detail?cas_rn=304-21-2"},{"name":"HMDB","url":"https://hmdb.ca/metabolites/HMDB0030310"},{"name":"KEGG","url":"https://www.kegg.jp/entry/C06536"},{"name":"UNII","url":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/CN58I4TOET"},{"name":"EPA DSSTox","url":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID8041038"}],"SMILES":"CC1=NCCC2=C1NC3=C2C=CC(=C3)OC","Solubility":"30.6 [ug/mL] (The mean of the results at pH 7.4)","StructureBase64":"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Uses":"/EXPL THER/ Oxidative modification of low-density lipoprotein (LDL) particles has been implicated in the process of atherogenesis. Antioxidants that prevent LDL from oxidation may reduce atherosclerosis. We have investigated the protective effect of Peganum harmala-extract (P-extract) and the two major alkaloids (harmine and harmaline) from the seeds of P. harmala against CuSO4-induced LDL oxidation. Through determination of the formation of malondialdehyde (MDA) and conjugated diene as well as the lag phase, the extract (P-extract) and compounds were found to possess an inhibitory effect. Moreover, harmaline and harmine reduced the rate of vitamin E disappearance and exhibited a significant free radical scavenging capacity (DPPH*). However, harmaline had a markedly higher antioxidant capacity than harmine in scavenging or preventive capacity against free radicals as well as inhibiting the aggregation of the LDL protein moiety (apolipoprotein B) induced by oxidation. The results suggested that P. harmala compounds could be a major source of compounds that inhibit LDL oxidative modification induced by copper.","Title":"Harmaline","UNII":"CN58I4TOET","Wikidata":"Q104252234","XLogP":2.1}