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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:06 UTC
Update Date2023-02-21 17:17:41 UTC
HMDB IDHMDB0012153
Secondary Accession Numbers
  • HMDB12153
Metabolite Identification
Common Name3,4-Dihydroxybenzylamine
Description3,4-Dihydroxybenzylamine is an alternative substrates for dopamine that is a member of the catecholamine family in the brain, and is a precursor to epinephrine and norepinephrine. Catecholamines contain a catechol group, and are derived from the amino acid and tyrosine. They are produced mainly by the chromaffin cells of the adrenal medulla and the postganglionic fibers of the sympathetic nervous system. Catecholamine synthesis is inhibited by alpha-Methyltyrosine, by inhibiting tyrosine-3 monooxygenase.Wikipedia.
Structure
Data?1676999861
Synonyms
ValueSource
4-(Aminomethyl)-1,2-benzenediolHMDB
4-(Aminomethyl)pyrocatechol hydrobromideHMDB
3,4-Dihydroxybenzylamine hydrobromideMeSH, HMDB
3,4-Dihydroxybenzylamine hydrochlorideMeSH, HMDB
3,4-DihydroxybenzylamineMeSH
Chemical FormulaC7H9NO2
Average Molecular Weight139.1519
Monoisotopic Molecular Weight139.063328537
IUPAC Name4-(aminomethyl)benzene-1,2-diol
Traditional Name3,4-dihydroxybenzylamine
CAS Registry Number37491-68-2
SMILES
NCC1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C7H9NO2/c8-4-5-1-2-6(9)7(10)3-5/h1-3,9-10H,4,8H2
InChI KeyYFMPSMITLLBENU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Benzylamine
  • Catechol
  • Phenylmethylamine
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility38.4 g/LALOGPS
logP-0.94ALOGPS
logP-0.066ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)9.61ChemAxon
pKa (Strongest Basic)8.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.49 m³·mol⁻¹ChemAxon
Polarizability14.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.7731661259
DarkChem[M-H]-126.23331661259
DeepCCS[M+H]+127.13430932474
DeepCCS[M-H]-123.30130932474
DeepCCS[M-2H]-160.55730932474
DeepCCS[M+Na]+136.09730932474
AllCCS[M+H]+130.432859911
AllCCS[M+H-H2O]+125.732859911
AllCCS[M+NH4]+134.732859911
AllCCS[M+Na]+135.932859911
AllCCS[M-H]-127.332859911
AllCCS[M+Na-2H]-129.032859911
AllCCS[M+HCOO]-131.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-DihydroxybenzylamineNCC1=CC=C(O)C(O)=C12458.6Standard polar33892256
3,4-DihydroxybenzylamineNCC1=CC=C(O)C(O)=C11596.5Standard non polar33892256
3,4-DihydroxybenzylamineNCC1=CC=C(O)C(O)=C11609.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxybenzylamine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(CN)C=C1O1541.5Semi standard non polar33892256
3,4-Dihydroxybenzylamine,1TMS,isomer #2C[Si](C)(C)OC1=CC(CN)=CC=C1O1532.7Semi standard non polar33892256
3,4-Dihydroxybenzylamine,1TMS,isomer #3C[Si](C)(C)NCC1=CC=C(O)C(O)=C11823.4Semi standard non polar33892256
3,4-Dihydroxybenzylamine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CN)C=C1O[Si](C)(C)C1597.0Semi standard non polar33892256
3,4-Dihydroxybenzylamine,2TMS,isomer #2C[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C)C(O)=C11725.9Semi standard non polar33892256
3,4-Dihydroxybenzylamine,2TMS,isomer #3C[Si](C)(C)NCC1=CC=C(O)C(O[Si](C)(C)C)=C11722.2Semi standard non polar33892256
3,4-Dihydroxybenzylamine,2TMS,isomer #4C[Si](C)(C)N(CC1=CC=C(O)C(O)=C1)[Si](C)(C)C1942.4Semi standard non polar33892256
3,4-Dihydroxybenzylamine,3TMS,isomer #1C[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11772.0Semi standard non polar33892256
3,4-Dihydroxybenzylamine,3TMS,isomer #1C[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11759.8Standard non polar33892256
3,4-Dihydroxybenzylamine,3TMS,isomer #1C[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11777.6Standard polar33892256
3,4-Dihydroxybenzylamine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C)[Si](C)(C)C)C=C1O1913.5Semi standard non polar33892256
3,4-Dihydroxybenzylamine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C)[Si](C)(C)C)C=C1O1920.6Standard non polar33892256
3,4-Dihydroxybenzylamine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C)[Si](C)(C)C)C=C1O1864.7Standard polar33892256
3,4-Dihydroxybenzylamine,3TMS,isomer #3C[Si](C)(C)OC1=CC(CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O1898.1Semi standard non polar33892256
3,4-Dihydroxybenzylamine,3TMS,isomer #3C[Si](C)(C)OC1=CC(CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O1924.5Standard non polar33892256
3,4-Dihydroxybenzylamine,3TMS,isomer #3C[Si](C)(C)OC1=CC(CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O1894.2Standard polar33892256
3,4-Dihydroxybenzylamine,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C1962.0Semi standard non polar33892256
3,4-Dihydroxybenzylamine,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C1887.0Standard non polar33892256
3,4-Dihydroxybenzylamine,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C1744.2Standard polar33892256
3,4-Dihydroxybenzylamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CN)C=C1O1825.1Semi standard non polar33892256
3,4-Dihydroxybenzylamine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(CN)=CC=C1O1807.8Semi standard non polar33892256
3,4-Dihydroxybenzylamine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NCC1=CC=C(O)C(O)=C12028.5Semi standard non polar33892256
3,4-Dihydroxybenzylamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CN)C=C1O[Si](C)(C)C(C)(C)C2125.2Semi standard non polar33892256
3,4-Dihydroxybenzylamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12225.5Semi standard non polar33892256
3,4-Dihydroxybenzylamine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12193.5Semi standard non polar33892256
3,4-Dihydroxybenzylamine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CC1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C2359.8Semi standard non polar33892256
3,4-Dihydroxybenzylamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12456.4Semi standard non polar33892256
3,4-Dihydroxybenzylamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12409.5Standard non polar33892256
3,4-Dihydroxybenzylamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12202.1Standard polar33892256
3,4-Dihydroxybenzylamine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O2599.4Semi standard non polar33892256
3,4-Dihydroxybenzylamine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O2534.5Standard non polar33892256
3,4-Dihydroxybenzylamine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O2223.0Standard polar33892256
3,4-Dihydroxybenzylamine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2583.5Semi standard non polar33892256
3,4-Dihydroxybenzylamine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2556.7Standard non polar33892256
3,4-Dihydroxybenzylamine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2240.9Standard polar33892256
3,4-Dihydroxybenzylamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2843.3Semi standard non polar33892256
3,4-Dihydroxybenzylamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2644.6Standard non polar33892256
3,4-Dihydroxybenzylamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2231.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzylamine GC-MS (Non-derivatized)splash10-0v4i-1895000000-17fe3f72ca5626566a5b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzylamine GC-MS (4 TMS)splash10-00di-1943200000-7e877068d51120c0bc8a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzylamine GC-MS (Non-derivatized)splash10-0v4i-1895000000-17fe3f72ca5626566a5b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzylamine GC-MS (Non-derivatized)splash10-00di-1943200000-7e877068d51120c0bc8a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxybenzylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2900000000-d832e8a8aed3df2e3f0d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxybenzylamine GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9570000000-a4c90864a7bd7b5594c42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxybenzylamine 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 - 3,4-Dihydroxybenzylamine 10V, Positive-QTOFsplash10-006x-0900000000-6ba4530eaf146a3cb2de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 20V, Positive-QTOFsplash10-00di-2900000000-353cda34c3fb2af030d02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 40V, Positive-QTOFsplash10-0gi1-9200000000-f84c60dd7e155912a06e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 10V, Negative-QTOFsplash10-000i-0900000000-9691fe2b85b62d0ab5992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 20V, Negative-QTOFsplash10-000i-1900000000-0a540f4ed71782ecb27b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 40V, Negative-QTOFsplash10-0a4l-9600000000-8c1cb6610b7d7d7d274f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 10V, Positive-QTOFsplash10-00di-1900000000-b74182e9a1455bf5aeee2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 20V, Positive-QTOFsplash10-00di-3900000000-a3272e9d97e12a96017b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 40V, Positive-QTOFsplash10-0gb9-9000000000-c74c6629e19a8fa3656f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 10V, Negative-QTOFsplash10-000i-0900000000-bcdad9cc7013b3dbe2ed2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 20V, Negative-QTOFsplash10-000i-1900000000-aeaf19f22da0179f796f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzylamine 40V, Negative-QTOFsplash10-00kf-9100000000-55d3a3ea77162b4a9ee52021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart 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 IDFDB028810
KNApSAcK IDNot Available
Chemspider ID82729
KEGG Compound IDNot Available
BioCyc IDCPD-7667
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91623
PDB IDNot Available
ChEBI IDNot Available
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