Harmaline (CHEM024334)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:38:24 UTC
Update Date2016-11-09 01:17:52 UTC
Accession NumberCHEM024334
Identification
Common NameHarmaline
ClassSmall Molecule
DescriptionA harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,4-DihydroharmineChEBI
7-Methoxy-1-methyl-4,9-dihydro-3H-beta-carbolineChEBI
ArmalinChEBI
DihydroharmineChEBI
HarmalinChEBI
Harmalol methyl etherChEBI
HarmidineChEBI
O-MethylharmalolChEBI
7-Methoxy-1-methyl-4,9-dihydro-3H-b-carbolineGenerator
7-Methoxy-1-methyl-4,9-dihydro-3H-β-carbolineGenerator
1-Methyl-7-methoxy-3, 4-dihydro-beta -carbolineHMDB
1-Methyl-7-methoxy-3,4-dihydro- beta-carbolineHMDB
1-Methyl-7-methoxy-3,4-dihydro-beta -carbolineHMDB
1-Methyl-7-methoxy-3,4-dihydro-beta-carbolineHMDB
3, 4-DihydroharmineHMDB
3,4-Dihydro-7-methoxy-1-methyl-9-pyrid(3,4-b)indoleHMDB
3,4-Dihydro-7-methoxy-1-methyl-9-pyrido(3,4-b)indoleHMDB
3,4-Dihydro-7-methoxy-1-methyl-9-pyrid[3,4-b]indoleHMDB
3,4-Dihydro-7-methoxy-1-methyl-b-carbolineHMDB
4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido(3,4-b)indoleHMDB
4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indoleHMDB
Dihydro-harmineHMDB
Chemical FormulaC13H14N2O
Average Molecular Mass214.263 g/mol
Monoisotopic Mass214.111 g/mol
CAS Registry Number304-21-2
IUPAC Name7-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole
Traditional Nameharmaline
SMILESCOC1=CC2=C(C=C1)C1=C(N2)C(C)=NCC1
InChI IdentifierInChI=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
InChI KeyRERZNCLIYCABFS-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
  • Harmaline
  • Harman
  • Beta-carboline
  • Pyridoindole
  • 3-alkylindole
  • Indole or derivatives
  • Indole
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Ketimine
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Ether
  • Organopnictogen compound
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Solubility0.058 g/LALOGPS
logP2.61ALOGPS
logP1.67ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.95ChemAxon
pKa (Strongest Basic)6.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.15 m³·mol⁻¹ChemAxon
Polarizability24.2 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-0900000000-8b0bbd88d925dd13fd02Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-2920000000-44473ef3fbb78c164b21Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-2920000000-44473ef3fbb78c164b21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0390000000-7a3eeedc85dd196eda22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1970000000-c7d3b2a8e9d823519fa4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-0900000000-c887581b709fc57e530fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0190000000-f7b71eafff989f146051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0390000000-3ce7a76fb334f9e591c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nb-1900000000-35911c2afac691df4c3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-f58ebef816fc4a8a6e35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0490000000-59b458e2ccd967f79f65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00l2-0900000000-6ad9c9837aa70579242bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-011b2ae80d93d1a6c938Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-011b2ae80d93d1a6c938Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-022a-1930000000-d1f321217affc513671dSpectrum
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 IDDB13875
HMDB IDHMDB0030310
FooDB IDFDB002148
Phenol Explorer IDNot Available
KNApSAcK IDC00001735
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHarmaline
Chemspider ID10211258
ChEBI ID28172
PubChem Compound ID3564
Kegg Compound IDC06536
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. de Sousa RC: [The cell membrane: a frontier between 2 worlds]. Schweiz Med Wochenschr. 1977 Nov 12;107(45):1605-12.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.