1-methyl-9H-pyrido[3,4-b]indole (CHEM021308)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 03:19:18 UTC
Update Date2016-11-09 01:17:19 UTC
Accession NumberCHEM021308
Identification
Common Name1-methyl-9H-pyrido[3,4-b]indole
ClassSmall Molecule
DescriptionAn indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.
Contaminant Sources
  • FooDB Chemicals
  • Suspected Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-Methyl-2-carbolineChEBI
1-Methyl-9H-beta-carbolineChEBI
1-Methyl-beta-carbolineChEBI
1-MethylnorharmanChEBI
AribinChEBI
AribineChEBI
HarmaneChEBI
L-MethylpyridobindoleChEBI
LocuturinChEBI
LocuturineChEBI
LoturineChEBI
PassiflorinChEBI
1-Methyl-9H-b-carbolineGenerator
1-Methyl-9H-β-carbolineGenerator
1-Methyl-b-carbolineGenerator
1-Methyl-β-carbolineGenerator
1-Methyl-9H-pyrido[3,4-b]indoleHMDB
1-Methyl-9H-pyrido[3,4-b]indole, 9ciHMDB
2-Methyl-beta-carbolineHMDB
3-Methyl-4-carbolineHMDB
L-Methyl-pyridobindoleHMDB
PassiflorineHMDB
ZygofabagineHMDB
Harman hydrochlorideHMDB
Chemical FormulaC12H10N2
Average Molecular Mass182.221 g/mol
Monoisotopic Mass182.084 g/mol
CAS Registry Number486-84-0
IUPAC Name1-methyl-9H-pyrido[3,4-b]indole
Traditional Nameharmane
SMILESCC1=C2NC3=CC=CC=C3C2=CC=N1
InChI IdentifierInChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3
InChI KeyPSFDQSOCUJVVGF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassHarmala alkaloids
Sub ClassNot Available
Direct ParentHarmala alkaloids
Alternative Parents
Substituents
  • Harman
  • Beta-carboline
  • Pyridoindole
  • Indole
  • Indole or derivatives
  • Methylpyridine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP3.36ALOGPS
logP2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)13.72ChemAxon
pKa (Strongest Basic)5.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.91 m³·mol⁻¹ChemAxon
Polarizability20.28 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-4900000000-2caa4dc9ec4e3750fe94Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-4900000000-2caa4dc9ec4e3750fe94Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-0900000000-1eb823770f43aa96d079Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-8a722b1b5d7b5941896bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-c3e22e3a50c1a33d3313Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-da3abe12c596a25c4fc7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00lr-0900000000-a0630fe37a9dae900711Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-fe40ad28de7c40fde973Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-2c091f7fb293a5702807Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-2900000000-37a11b66e75cedf3e072Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-2900000000-753e83180abd8e8f4306Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-053r-4900000000-a0c45efe16d695cf0465Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-2900000000-4e2e84a5d7cb4f3b6e5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , negativesplash10-001i-0900000000-da5f8f71b14a2afaf96bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-b61926dd87fa8a8bf547Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-be2b3d6251e5698ec184Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-2467a87546dc5758f74cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-6222b796373c7d683eddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-5f9fc354bf2eb82f440cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-8f767ae14c8cb390abd4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-3206fb22991bbadfb410Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-fbe37bd173c6820a5fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-f0389c36d5ddc1a056cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-f4d0d496031eda8faccaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-0900000000-24a22633d62b61cf09b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-c6d6c9589b7c3045e05eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-155dea2165739f0af46eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-067i-0900000000-78073f143aded0ccce81Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0035196
FooDB IDFDB021482
Phenol Explorer IDNot Available
KNApSAcK IDC00001736
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHarman
Chemspider ID4444755
ChEBI ID5623
PubChem Compound ID5281404
Kegg Compound IDC09209
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11473435
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19645722
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20732341
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22757671
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22981972
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23544153
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24103378
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24300779
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24486683
10. Abramets II, Dolzhenko AT: [Harman and its derivatives as potential atypical antidepressants]. Farmakol Toksikol. 1986 Jul-Aug;49(4):15-9.
11. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.