08472

Harmaline

analytical standard

• 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
• Beilstein: 207310
• EC Number: 206-152-6
• MDL number: MFCD00004955
• UNSPSC Code: 41116107
• NACRES: NA.24

Properties

• grade: analytical standard
• Quality Level: 100
• Assay: ≥95.0% (HPLC)
• shelf life: limited shelf life, expiry date on the label
• drug control: stupéfiant (France); regulated under CDSA - not available from Sigma-Aldrich Canada
• mp: 232-234 °C (lit.)
• format: neat
• 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

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Warning
• Hazard Statements: H302,H371
• Precautionary Statements: P260 - P264 - P301 + P312 - P308 + P311 - P405 - P501
• Hazard Classifications: Acute Tox. 4 Oral - STOT SE 2
• Target Organs: Central nervous system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable