1,2,3,4-Tetrahydro-beta-carboline (CHEM040919)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:04:40 UTC
Update Date2016-11-09 01:22:21 UTC
Accession NumberCHEM040919
Identification
Common Name1,2,3,4-Tetrahydro-beta-carboline
ClassSmall Molecule
DescriptionTetrahydro-b-carbolines (THbCs)are potential neuroactive alkaloids found in chocolate and cocoa. The formation of 1,2,3,4-tetrahydro-/3-carbolines (THBCs), via the Pictet-Spengler condensation of tryptamines with formaldehyde, has been demonstrated repeatedly in incubations of various mammalian tissues containing added indolethylamine substrate and the methyl donors .5-methyltetrahydrofolate (5-MTHF) or S-adenosylmethionine(SAM). It is concluded that the formation of these THBCs is an artifact produced by the enzymatic liberation of formaldehyde from the methyl donors and the subsequent non-enzymatic condensation of this formaldehyde with the indole substrates. The formation of THBCs in vivo has thus remained a point of contention. (PMID: 7213417). 1,2,3,4-Tetrahydro-beta-carboline is a biomarker for the consumption of beer
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3,4-Tetrahydro-b-carbolineGenerator
1,2,3,4-Tetrahydro-β-carbolineGenerator
1,2,3,4-TetrahydronorharmaneHMDB
THBCHMDB
Tryptoline hydrochlorideMeSH, HMDB
THbetaCMeSH, HMDB
TetrahydronorharmaneMeSH, HMDB
9H-1,2,3,4-tetrahydropyrido(3,4-b)IndoleMeSH, HMDB
NoreleagnineMeSH, HMDB
tetrahydro-beta-CarbolineMeSH, HMDB
Tryptoline monohydrochlorideMeSH, HMDB
TriptolineMeSH, HMDB
1,2,3,4-Tetrahydro-beta-carbolineMeSH
TryptolineMeSH
Chemical FormulaC11H12N2
Average Molecular Mass172.226 g/mol
Monoisotopic Mass172.100 g/mol
CAS Registry NumberNot Available
IUPAC Name1H,2H,3H,4H,9H-pyrido[3,4-b]indole
Traditional Nametryptoline
SMILESC1CC2=C(CN1)NC1=C2C=CC=C1
InChI IdentifierInChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2
InChI KeyCFTOTSJVQRFXOF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyridoindoles
Direct ParentBeta carbolines
Alternative Parents
Substituents
  • Beta-carboline
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.43 g/LALOGPS
logP1.31ALOGPS
logP1.59ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)16.46ChemAxon
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area27.82 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity53.58 m³·mol⁻¹ChemAxon
Polarizability19.62 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, Positivesplash10-0596-0900000000-0c12ea5ede1ecce0b8a0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-3900000000-59256f2013af0388b609Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0900000000-298d086f2db7bfb96c7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-3900000000-59256f2013af0388b609Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-0900000000-0e95cd13061c8268d13dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-d1cf77f85d424207ea20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0900000000-fa3e868e9ca6a59d5b91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0560-0900000000-76a12e37b5faa4cbb856Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-2305b865b13eae850bbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-d58681edbdcc31aced92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-0900000000-3e4b9943ce69d390f2aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ff5f70dda818b9673030Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-1b2e7c8ce9fa45740ef0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00bc-2900000000-f5466bd5eff0535cb5b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-84df739a23ca1993145cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-84df739a23ca1993145cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-234e77ff29e2c2061761Spectrum
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 IDHMDB0012488
FooDB IDFDB029095
Phenol Explorer IDNot Available
KNApSAcK IDC00052418
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID96979
ChEBI ID100417
PubChem Compound ID107838
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Barker SA, Harrison RE, Monti JA, Brown GB, Christian ST: Identification and quantification of 1,2,3,4-tetrahydro-beta-carboline, 2-methyl-1,2,3,4-tetrahydro-beta-carboline, and 6-methoxy-1,2,3,4-tetrahydro-beta-carboline as in vivo constituents of rat brain and adrenal gland. Biochem Pharmacol. 1981 Jan 1;30(1):9-17.