7-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole

• ChemBase ID: 102502
• Molecular Formular: C13H14N2O
• Molecular Mass: 214.26306
• Monoisotopic Mass: 214.11061308
• SMILES: COc1cc2c(cc1)c1c([nH]2)C(=NCC1)C
• Canonical SMILES: COc1ccc2c(c1)[nH]c1c2CCN=C1C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole
• IUPAC Traditional name: harmaline; 7-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole
• Synonyms: 1-Methyl-7-methoxy-3,4-dihydro-β-carboline; Dihydroharmine; Harmalol methyl ether; 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole; HARMALINE; Harmidine; NSC 407285; 1-Methyl-7-methoxy-3,4-dihydro-β-carboline; Harmaline; 1-Methyl-7-methoxy-3,4-dihydro-β-carboline hydrochloride; 1-甲基-7-甲氧基-3,4-二氢-β-咔啉; 3,4-二氢骆驼蓬碱; 7-甲氧基-1-甲基-4,9-二氢-3H-吡啶并[3,4-b]吲哚; O-甲基骆驼蓬酚; 骆驼蓬灵

Database IDs

• CAS Number: 6027-98-1; 304-21-2
• EC Number: 206-152-6
• MDL Number: MFCD00004955
• Beilstein Number: 207310
• PubChem SID: 24873687; 162088113
• PubChem CID: 5280951
• CHEBI ID: 28172
• CHEMBL: 340807
• Chemspider ID: 10211258
• KEGG ID: C06536
• Unique Ingredient Identifier: CN58I4TOET
• Wikipedia Title: Harmaline

CALCULATED PROPERTIES

• Acid pKa: 14.954947
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.750205
• LogD (pH = 7.4): 1.0009356
• Log P: 1.6682112
• Molar Refractivity: 64.1514 cm^3
• Polarizability: 25.353348 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 232–234 °C; 232-234 °C(lit.)

Safety Information

• Storage Condition: 0°C
• RTECS: MG8750000; UU9800000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada; stupéfiantregulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• 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)
• Mechanism of Action: CNS stimulant; MAO inhibitor

Product Information

• Purity: 97%; 98.5
• Biological Source: Alkaloid from Peganum harmala, Passiflora incarnata, Banisteria caapi and some Banisteriopsis spp. (Zygophyllaceae, Passifloraceae, Malphigiaceae)
• Application(s): Component of a S. American hallucinogenic drink; Possesses antiparkinsonian props.
• Empirical Formula (Hill Notation): C13H14N2O

DETAILS

MP Biomedicals - 02101915

Free Base
Crystalline
Fluoresces blue in solution.

MP Biomedicals - 02151225

Hydrochloride
Crystalline
Dihydrate
Monoamine oxidase inhibitor

MP Biomedicals - 05211576

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 51330

Biochem/physiol Actions
CNS stimulant; may act through NMDA receptors
Packaging
1 g in glass bottle
Application
Reactant for preparation of:
• Acylated harmalines via Friedel-Crafts reaction1
• Phenacyl derivatives of 1-methyl-7-methoxy-β-carbolines as central nervous system affectors2
• Palladium harmaline DMSO chloro complex as anti-tumor agent3Natural product scaffold in preparation of:
• Trypanothione reductase inhibitors†

Sigma Aldrich - 286036

Biochem/physiol Actions
CNS stimulant; may act through NMDA receptors
Application
Reactant for preparation of:
• Acylated harmalines via Friedel-Crafts reaction1
• Phenacyl derivatives of 1-methyl-7-methoxy-β-carbolines as central nervous system affectors2
• Palladium harmaline DMSO chloro complex as anti-tumor agent3Natural product scaffold in preparation of:
• Trypanothione reductase inhibitors†

REFERENCES

• Fischer, O., Ber., 1889, 22, 637, (synth)
• Spth, E. et al., Ber., 1930, 63, 120, (Me ether, synth)
• Konovalova, R. et al., Arch. Pharm. (Weinheim, Ger.), 1935, 273, 156, (synth)
• Spenser, I.D., Can. J. Chem., 1959, 37, 1851, (derivs, synth, uv, ir)
• Robinson, B., Chem. Ind. (London), 1965, 605, (Me ether, pmr)
• Allen, J.R.F. et al., Phytochemistry, 1980, 19, 1573, (occur, bibl)
• Coune, C.A. et al., Phytochemistry, 1980, 19, 2009, (cmr)
• Verpoorte, R. et al., Org. Magn. Reson., 1984, 22, 328, (cmr)
• Biondic, M.C. et al., J.C.S. Perkin 2, 1992, 1049, (Me ether, uv)