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

• ChemBase ID: 5549
• Molecular Formular: C13H12N2O
• Molecular Mass: 212.24718
• Monoisotopic Mass: 212.09496301
• SMILES: Cc1nccc2c1[nH]c1cc(ccc21)OC
• Canonical SMILES: COc1ccc2c(c1)[nH]c1c2ccnc1C
• InChI: InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
• InChIKey: BXNJHAXVSOCGBA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
• IUPAC Traditional name: harmine; 7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
• Synonyms: Harmine; 7-Methoxy-1-methyl-β-carboline; 6-Methoxyharmane; 7-METHOXY-1-METHYL-9H-BETA-CARBOLINE; 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole; HARMINE; Leucoharmine; Telepathin; Telepathine; Yagein; Yageine; 1-Methyl-7-methoxy-β-carboline; Banisterin; Banisterine; Harmin; 7-甲氧基-1-甲基-9H-吡啶并[3,4-b]吲哚; 肉叶云香碱; 骆驼蓬碱

Database IDs

• CAS Number: 442-51-3
• EC Number: 207-131-4
• MDL Number: MFCD00004958
• Beilstein Number: 178813
• Merck Index: 144616
• PubChem SID: 160968977; 24857229; 24873729; 99444390
• PubChem CID: 5280953
• CHEBI ID: 28121
• CHEMBL: 269538
• Chemspider ID: 4444445
• DrugBank ID: DB07919
• KEGG ID: C06538
• Unique Ingredient Identifier: 4FHH5G48T7
• Wikipedia Title: Harmine

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.542986
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.1702937
• LogD (pH = 7.4): 1.8238173
• Log P: 1.8469121
• Molar Refractivity: 62.37 cm^3
• Polarizability: 26.53343 Å^3
• Polar Surface Area: 37.91 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.05
• LOG S: -3.54
• Solubility (Water): 6.13e-02 g/l

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White to Orange Solid; Powder
• Melting Point: >230°C (dec.); 262-264 °C(lit.); 262-266°C; 321 °C (·HCl); 262 °C (·HCl·2H₂O)

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: UV0175000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36; 20/22-36
• Safety Statements: 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H319-H332; H302-H332-H319
• GHS Precautionary statements: P280H-P305+P351+P338; P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... CDC2(983), CYP2D6(1565)
• Mechanism of Action: CNS stimulant; MAO-A inhibitor

Product Information

• Purity: ≥98.0% (NT); 98%; 98.5; 98+%
• Grade: purum
• Biological Source: Alkaloid from Peganum harmala, several Banisteriopsis spp., Passiflora edulis and several other spp. (Zygophyllaceae, Malphigiaceae, Passifloraceae)
• Application(s): Active against gram-positive bacteria and fungi; Antiparkinsonian agent
• Empirical Formula (Hill Notation): C13H12N2O

DETAILS

MP Biomedicals - 02157296

Free Base
White crystals.

DrugBank - DB07919

Drug information: experimental

Sigma Aldrich - 286044

Biochem/physiol Actions
Central nervous system stimulant.
Packaging
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 51400

Biochem/physiol Actions
Central nervous system stimulant.

Toronto Research Chemicals - H105250

A CNS stimulant isolated from seeds of Peganum harmala L. Zygophyllaceae.

REFERENCES

• Chen, K.K., et al.: J. Pharmacol. Exp. Ther., 79, 127 (1943)
• DiStefano, S., et al.: J. Pharmacol. Exp. Ther., 174, 456 (1943)
• Ahmad, A. et al., J. Ethnopharmacol., 1992, 35, 289-294, (activity)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1376
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HAI500
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 682C, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 166B; 166C, (nmr)
• Spth, E. et al., Ber., 1930, 63, 120, (synth)
• Ismailov, N.A. et al., Farm. Farmakol, 1938, 4, 8, (use)
• Doig, G.G. et al., J.C.S., 1952, 3912, (uv)
• Schlittler, E. et al., Helv. Chim. Acta, 1953, 36, 996, (synth)
• Bishop, E., Indicators, Pergamon, Oxford, 1972, 695, (use)
• Hernandez, N.M.R. et al., Rev. Cubana Farm., 1977, 11, 249-255, (activity)
• Shoemaker, D.W. et al., J. Chromatogr., 1979, 174, 159, (glc, ms)
• Ross, S.A. et al., Fitoterapia, 1980, 6, 309-312, (activity)
• Al-Shamma, A. et al., J. Nat. Prod., 1981, 44, 745-747, (activity)
• Siddiqui, S. et al., Heterocycles, 1989, 29, 521, (isol, uv, ir, pmr, ms, bibl, Norharmine)