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442-51-3 molecular structure
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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 and InChIs

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

Cite this record

CBID:5549 http://www.chembase.cn/molecule-5549.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
442-51-3
EC Number
207-131-4
MDL Number
MFCD00004958
Beilstein Number
178813
Merck Index
144616
PubChem SID
24873729
99444390
24857229
160968977
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.542986  H Acceptors
H Donor LogD (pH = 5.5) 1.1702937 
LogD (pH = 7.4) 1.8238173  Log P 1.8469121 
Molar Refractivity 62.37 cm3 Polarizability 26.53343 Å3
Polar Surface Area 37.91 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.05  LOG S -3.54 
Solubility (Water) 6.13e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Methanol expand Show data source
Apperance
Off-White to Orange Solid expand Show data source
Powder expand Show data source
Melting Point
>230°C (dec.) expand Show data source
262-264 °C(lit.) expand Show data source
262-266°C expand Show data source
321 °C (·HCl); 262 °C (·HCl·2H2O) expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
UV0175000 expand Show data source
European Hazard Symbols
X expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
20/21/22-36 expand Show data source
20/22-36 expand Show data source
Safety Statements
26-36/37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H312-H319-H332 expand Show data source
H302-H332-H319 expand Show data source
GHS Precautionary statements
P280H-P305+P351+P338 expand Show data source
P280-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Gene Information
human ... CDC2(983), CYP2D6(1565) expand Show data source
Mechanism of Action
CNS stimulant expand Show data source
MAO-A inhibitor expand Show data source
Purity
≥98.0% (NT) expand Show data source
98% expand Show data source
98.5 expand Show data source
98+% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Biological Source
Alkaloid from Peganum harmala, several Banisteriopsis spp., Passiflora edulis and several other spp. (Zygophyllaceae, Malphigiaceae, Passifloraceae) expand Show data source
Application(s)
Active against gram-positive bacteria and fungi expand Show data source
Antiparkinsonian agent expand Show data source
Empirical Formula (Hill Notation)
C13H12N2O expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02157296 external link
Free Base
White crystals.
DrugBank - DB07919 external link
Drug information: experimental
Sigma Aldrich - 286044 external link
Biochem/physiol Actions
Central nervous system stimulant.
Packaging
1 g in glass bottle
250 mg in glass bottle
Sigma Aldrich - 51400 external link
Biochem/physiol Actions
Central nervous system stimulant.
Toronto Research Chemicals - H105250 external link
A CNS stimulant isolated from seeds of Peganum harmala L. Zygophyllaceae.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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