51330

Harmaline

≥95%

• 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: 12352100
• PubChem Substance ID: 57651320
• NACRES: NA.22

Properties

• Assay: ≥95%
• form: powder
• 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
• Gene Information: human ... ADRA1A(148) , ADRA1B(147) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152) , ADRB1(153) , ADRB2(154) , CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133) , DRD1(1812) , DRD5(1816) , HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR2C(3358) , HTR3A(3359) , HTR5A(3361) , HTR6(3362) , HTR7(3363) , SLC6A2(6530) , SLC6A4(6532) , SLC9A2(6549) , SLC9A5(6553) ; rat ... Drd2(24318) , Drd3(29238) , Drd4(25432) , Htr2a(29595) , Maoa(29253) , Maob(25750) , Slc9a1(24782) , Slc9a3(24784)

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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves