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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:01:34 UTC
Update Date2023-02-21 17:17:49 UTC
HMDB IDHMDB0012489
Secondary Accession Numbers
  • HMDB12489
Metabolite Identification
Common Name1,2,3,4-Tetrahydroisoquinoline
DescriptionTetrahydroisoquinoline is a secondary amine with the chemical formula C9H11N.Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.The tetrahydroisoquinoline skeleton is commonly encountered in pharmaceutical drugs, notably quaternary ammonium muscle relaxants. Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism.This theory has now been discredited and is no longer generally accepted by the scientific community, but endogenous production of neurotoxic tetrahydroisoquinoline derivatives such as norsalsolinol continue to be investigated as possible causes for some conditions such as Parkinson's disease.{from wiki).
Structure
Data?1676999869
Synonyms
ValueSource
1234-TetrahydroisoquinolineChEMBL, HMDB
1234-tetrahydro-IsoquinolineChEMBL, HMDB
TetrahydroisoquinolineHMDB, MeSH
1,2,3,4-tetrahydro-2-AzanaphthaleneHMDB, MeSH
1,2,3,4-tetrahydro-2-IsoquinolineHMDB
1,2,3,4-TetrahydroleucolineHMDB
HCL OF 1,2,3,4-TetrahydroisoquinolineMeSH, HMDB
3,4-Dihydro-1H-isoquinolineMeSH
Chemical FormulaC9H11N
Average Molecular Weight133.1903
Monoisotopic Molecular Weight133.089149357
IUPAC Name1,2,3,4-tetrahydroisoquinoline
Traditional Nametetrahydroisoquinoline
CAS Registry Number14099-81-1
SMILES
C1CC2=C(CN1)C=CC=C2
InChI Identifier
InChI=1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2
InChI KeyUWYZHKAOTLEWKK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
  • Aralkylamine
  • Benzenoid
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< -15 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.81 g/LALOGPS
logP1.31ALOGPS
logP1.57ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)9.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.62 m³·mol⁻¹ChemAxon
Polarizability15.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+126.77931661259
DarkChem[M-H]-123.7831661259
DeepCCS[M+H]+130.230932474
DeepCCS[M-H]-126.76830932474
DeepCCS[M-2H]-164.09730932474
DeepCCS[M+Na]+139.17730932474
AllCCS[M+H]+126.932859911
AllCCS[M+H-H2O]+122.032859911
AllCCS[M+NH4]+131.432859911
AllCCS[M+Na]+132.832859911
AllCCS[M-H]-128.532859911
AllCCS[M+Na-2H]-129.832859911
AllCCS[M+HCOO]-131.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,2,3,4-TetrahydroisoquinolineC1CC2=C(CN1)C=CC=C21838.9Standard polar33892256
1,2,3,4-TetrahydroisoquinolineC1CC2=C(CN1)C=CC=C21233.4Standard non polar33892256
1,2,3,4-TetrahydroisoquinolineC1CC2=C(CN1)C=CC=C21264.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,2,3,4-Tetrahydroisoquinoline,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC=CC=C2C11428.5Semi standard non polar33892256
1,2,3,4-Tetrahydroisoquinoline,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC=CC=C2C11385.5Standard non polar33892256
1,2,3,4-Tetrahydroisoquinoline,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC=CC=C2C11736.3Standard polar33892256
1,2,3,4-Tetrahydroisoquinoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C11670.3Semi standard non polar33892256
1,2,3,4-Tetrahydroisoquinoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C11654.2Standard non polar33892256
1,2,3,4-Tetrahydroisoquinoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C11941.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline EI-B (Non-derivatized)splash10-001i-7900000000-880ecb945a866c58a8692017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline EI-B (Non-derivatized)splash10-001i-7900000000-880ecb945a866c58a8692018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-100r-2900000000-241c80cb6dc81b9b83e02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 10V, Positive-QTOFsplash10-001i-0900000000-9cda6a8e29a836be071a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 20V, Positive-QTOFsplash10-00lr-1900000000-0fffb087a6b9e5f092fa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 40V, Positive-QTOFsplash10-066u-9800000000-ed1397065d659994d9962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 10V, Negative-QTOFsplash10-001i-0900000000-8b124bc9800fbbc9a3c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 20V, Negative-QTOFsplash10-001i-0900000000-7c43cb3e6b9cef43d2212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 40V, Negative-QTOFsplash10-0uyi-3900000000-58d4ecc958f729594d6b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 10V, Positive-QTOFsplash10-001i-1900000000-750b3fc0ed1857cd3d2e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 20V, Positive-QTOFsplash10-001l-4900000000-c1118a9a9962f041fb342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 40V, Positive-QTOFsplash10-0006-9100000000-2ee9aad24737bda777962021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 10V, Negative-QTOFsplash10-001i-0900000000-163cef49a8efd2ca85d52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 20V, Negative-QTOFsplash10-001i-0900000000-7cb157b4702fa57056e62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 40V, Negative-QTOFsplash10-0ge9-2900000000-53cc67b7ef90d1c880f42021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB029096
KNApSAcK IDNot Available
Chemspider ID6779
KEGG Compound IDNot Available
BioCyc IDDIHYDRO-DIOH-BENZOATE
BiGG IDNot Available
Wikipedia LinkTetrahydroisoquinoline
METLIN IDNot Available
PubChem Compound7046
PDB IDNot Available
ChEBI ID114116
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 ReferencesNot Available