286036

Harmaline

97%

• Synonym(s): 1-Methyl-7-methoxy-3,4-dihydro-β-carboline, 3,4-Dihydroharmine, 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole, Dihydroharmine, Harmalol methyl ether, Harmidine, NSC 407285
• Empirical Formula (Hill Notation): C₁₃H₁₄N₂O
• CAS Number: 304-21-2
• Molecular Weight: 214.26
• EC Number: 206-152-6
• UNSPSC Code: 12352100
• MDL number: MFCD00004955
• Beilstein/REAXYS Number: 207310
• eCl@ss: 32160701

Properties

• assay: 97%
• drug control: regulated under CDSA - not available from Sigma-Aldrich Canada, stupéfiant (France); regulated under CDSA - not available from Sigma-Aldrich Canada
• mp: 232-234 °C (lit.)
• SMILES string: COc1ccc2c3CCN=C(C)c3[nH]c2c1
• 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
• InChI key: RERZNCLIYCABFS-UHFFFAOYSA-N

Description

Application

Reactant for preparation of:

• Acylated harmalines via Friedel-Crafts reaction
• Phenacyl derivatives of 1-methyl-7-methoxy-β-carbolines as central nervous system affectors
• Palladium harmaline DMSO chloro complex as anti-tumor agent

Natural product scaffold in preparation of:

• Trypanothione reductase inhibitors†

Biochem/physiol Actions

CNS stimulant; may act through NMDA receptors