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6027-98-1 molecular structure
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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 and InChIs

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

Cite this record

CBID:102502 http://www.chembase.cn/molecule-102502.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
1-Methyl-7-methoxy-3,4-dihydro-β-carboline hydrochloride
HARMALINE
Harmidine
NSC 407285
1-Methyl-7-methoxy-3,4-dihydro-β-carboline
Harmaline
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
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

CALCULATED PROPERTIES

JChem
Acid pKa 14.954947  H Acceptors
H Donor LogD (pH = 5.5) -0.750205 
LogD (pH = 7.4) 1.0009356  Log P 1.6682112 
Molar Refractivity 64.1514 cm3 Polarizability 25.353348 Å3
Polar Surface Area 37.38 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Apperance
Powder expand Show data source
Melting Point
232–234 °C expand Show data source
232-234 °C(lit.) expand Show data source
Storage Condition
0°C expand Show data source
RTECS
MG8750000 expand Show data source
UU9800000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) 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
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
R:36/37/38 expand Show data source
Safety Statements
S:20-25-26-37/39 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Drug Control
regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
stupéfiantregulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
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) expand Show data source
Mechanism of Action
CNS stimulant expand Show data source
MAO inhibitor expand Show data source
Purity
97% expand Show data source
98.5 expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Biological Source
Alkaloid from Peganum harmala, Passiflora incarnata, Banisteria caapi and some Banisteriopsis spp. (Zygophyllaceae, Passifloraceae, Malphigiaceae) expand Show data source
Application(s)
Component of a S. American hallucinogenic drink expand Show data source
Possesses antiparkinsonian props. expand Show data source
Empirical Formula (Hill Notation)
C13H14N2O expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02151225 external link
Hydrochloride
Crystalline
Dihydrate
Monoamine oxidase inhibitor
MP Biomedicals - 05211576 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02101915 external link
Free Base
Crystalline
Fluoresces blue in solution.
Sigma Aldrich - 286036 external link
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†
Sigma Aldrich - 51330 external link
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†

REFERENCES

REFERENCES

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

PATENTS

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