Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:01:33 UTC
Update Date2023-02-21 17:17:49 UTC
HMDB IDHMDB0012488
Secondary Accession Numbers
  • HMDB12488
Metabolite Identification
Common Name1,2,3,4-Tetrahydro-beta-carboline
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
Structure
Data?1676999869
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 Weight172.2264
Monoisotopic Molecular Weight172.100048394
IUPAC Name1H,2H,3H,4H,9H-pyrido[3,4-b]indole
Traditional Nametryptoline
CAS Registry NumberNot Available
SMILES
C1CC2=C(CN1)NC1=C2C=CC=C1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.86831661259
DarkChem[M-H]-136.82331661259
DeepCCS[M+H]+135.85730932474
DeepCCS[M-H]-133.17730932474
DeepCCS[M-2H]-168.96630932474
DeepCCS[M+Na]+144.50430932474
AllCCS[M+H]+137.132859911
AllCCS[M+H-H2O]+132.532859911
AllCCS[M+NH4]+141.332859911
AllCCS[M+Na]+142.532859911
AllCCS[M-H]-140.832859911
AllCCS[M+Na-2H]-140.932859911
AllCCS[M+HCOO]-141.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,2,3,4-Tetrahydro-beta-carbolineC1CC2=C(CN1)NC1=C2C=CC=C12940.9Standard polar33892256
1,2,3,4-Tetrahydro-beta-carbolineC1CC2=C(CN1)NC1=C2C=CC=C11862.9Standard non polar33892256
1,2,3,4-Tetrahydro-beta-carbolineC1CC2=C(CN1)NC1=C2C=CC=C11951.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #1C[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C212071.0Semi standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #1C[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C211919.5Standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #1C[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C212411.6Standard polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #2C[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C211995.8Semi standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #2C[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C211755.9Standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #2C[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C212316.2Standard polar33892256
1,2,3,4-Tetrahydro-beta-carboline,2TMS,isomer #1C[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C)C1=CC=CC=C212054.8Semi standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,2TMS,isomer #1C[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C)C1=CC=CC=C212041.7Standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,2TMS,isomer #1C[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C)C1=CC=CC=C212232.2Standard polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C212317.1Semi standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C212147.1Standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C212617.7Standard polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C212220.2Semi standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C211989.8Standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C212421.5Standard polar33892256
1,2,3,4-Tetrahydro-beta-carboline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C212473.8Semi standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C212477.3Standard non polar33892256
1,2,3,4-Tetrahydro-beta-carboline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C212488.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-0900000000-0c12ea5ede1ecce0b8a02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline LC-ESI-qTof , Positive-QTOFsplash10-0006-3900000000-59256f2013af0388b6092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline , positive-QTOFsplash10-0006-0900000000-298d086f2db7bfb96c7f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline , positive-QTOFsplash10-0006-3900000000-59256f2013af0388b6092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 35V, Positive-QTOFsplash10-0006-0900000000-0e95cd13061c8268d13d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 10V, Positive-QTOFsplash10-00di-0900000000-d1cf77f85d424207ea202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 20V, Positive-QTOFsplash10-006x-0900000000-fa3e868e9ca6a59d5b912017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 40V, Positive-QTOFsplash10-0560-0900000000-76a12e37b5faa4cbb8562017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 10V, Negative-QTOFsplash10-00di-0900000000-2305b865b13eae850bbb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 20V, Negative-QTOFsplash10-00di-0900000000-d58681edbdcc31aced922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 40V, Negative-QTOFsplash10-0596-0900000000-3e4b9943ce69d390f2aa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 10V, Positive-QTOFsplash10-00di-0900000000-ff5f70dda818b96730302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 20V, Positive-QTOFsplash10-00di-0900000000-1b2e7c8ce9fa45740ef02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 40V, Positive-QTOFsplash10-00bc-2900000000-f5466bd5eff0535cb5b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 10V, Negative-QTOFsplash10-00di-0900000000-84df739a23ca1993145c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 20V, Negative-QTOFsplash10-00di-0900000000-84df739a23ca1993145c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 40V, Negative-QTOFsplash10-0006-0900000000-234e77ff29e2c20617612021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029095
KNApSAcK IDC00052418
Chemspider ID96979
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107838
PDB IDNot Available
ChEBI ID100417
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:7213417 ]