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Record Information
Version1.0
Creation Date2016-09-30 22:19:18 UTC
Update Date2020-06-04 18:58:57 UTC
MCDB ID BMDB0000073
Secondary Accession Numbers
  • BMDB00073
Metabolite Identification
Common NameDopamine
DescriptionDopamine, also known as 3-hydroxytyramine or deoxyepinephrine, belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution. Dopamine is a drug which is used for the correction of hemodynamic imbalances present in the shock syndrome due to myocardial infarction, trauma, endotoxic septicemia, open-heart surgery, renal failure, and chronic cardiac decompensation as in congestive failure. Dopamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Dopamine exists in all living organisms, ranging from bacteria to humans. Dopamine participates in a number of enzymatic reactions, within cattle. In particular, Dopamine can be converted into dopamine; which is catalyzed by the enzyme D(1a) dopamine receptor. In addition, Dopamine can be converted into dopamine through its interaction with the enzyme D(1a) dopamine receptor. In cattle, dopamine is involved in the metabolic pathway called the dopamine activation OF neurological reward system pathway. Dopamine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)ethylamineChEBI
3,4-DihydroxyphenethylamineChEBI
3-HydroxytyramineChEBI
4-(2-Aminoethyl)-1,2-benzenediolChEBI
4-(2-Aminoethyl)benzene-1,2-diolChEBI
4-(2-Aminoethyl)catecholChEBI
4-(2-Aminoethyl)pyrocatecholChEBI
DeoxyepinephrineChEBI
DopaminaChEBI
DopaminumChEBI
HydroxytyraminChEBI
MedopaKegg
3,4-DihydroxyphenylethylamineHMDB
4-(2-Aminoethyl)-pyrocatecholHMDB
a-(3,4-Dihydroxyphenyl)-b-aminoethaneHMDB
alpha-(3,4-Dihydroxyphenyl)-beta-aminoethaneHMDB
DopaminHMDB
DopastatHMDB
DophamineHMDB
DynatraHMDB
HydroxytyramineHMDB
IntropinHMDB
OxytyramineHMDB
RevivanHMDB
3,4 DihydroxyphenethylamineHMDB
Hydrochloride, dopamineHMDB
Dopamine hydrochlorideHMDB
Chemical FormulaC8H11NO2
Average Molecular Weight153.1784
Monoisotopic Molecular Weight153.078978601
IUPAC Name4-(2-aminoethyl)benzene-1,2-diol
Traditional Namedopamine
CAS Registry Number62-31-7
SMILES
NCCC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2
InChI KeyVYFYYTLLBUKUHU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • Catecholamine
  • Phenethylamine
  • 2-arylethylamine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point128 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility535 mg/mLNot Available
LogP-0.98HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.4ALOGPS
logP0.03ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
pKa (Strongest Basic)9.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.25 m³·mol⁻¹ChemAxon
Polarizability16.21 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1900000000-117a1a7207245f5377e72014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-1900000000-8b7dcae82868308513da2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-117a1a7207245f5377e72017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1900000000-8b7dcae82868308513da2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-8900000000-752bc8c11fa321b8a7ac2017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-9280000000-c894c19dda88ac048dd42017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uxu-4900000000-ff51177ebcb89b8c956c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9200000000-a554eb700a06cecb82922012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-db9813e1025f237a549b2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-27e0d71db6d14d79759c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0uk9-0900000000-f1cf97c0d0dd509e229e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-0900000000-aa09a2411e287abe74ed2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-1900000000-97c42b109cab2005373d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-006x-9700000000-974bd18febffcceea2d62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0f79-0900000000-099173d4201beca9e5482012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-9dc09f2661247c9d84b02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9300000000-8b85fa9aac1ffb4c28732012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-9ea16d2057010279d4332012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-9000000000-32ca2db8fe2b4729ab942012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0f79-0900000000-ff587935c79b4592ffcf2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-8a35d8a2241bc18d6c502012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9300000000-356a4b8f268863c7893e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-a88c1004f357858fbc6c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-9000000000-271874005dcb902885122012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0900000000-cfa7e1cb9f02ffb4447d2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-4e409c6edda911de39fe2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-90aa0e0866454c2eacc72017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9400000000-210fd696305d8cf761642017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-ff95007680e484d3c57e2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-6dcfecebbd98220ef7462017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kil-6900000000-f476cfd569c441bc84aa2017-06-28View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00e9-8900000000-88acdc978fe4a64e0fc52014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000073
DrugBank IDDB00988
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012163
KNApSAcK IDC00001408
Chemspider ID661
KEGG Compound IDC03758
BioCyc IDDOPAMINE
BiGG ID42467
Wikipedia LinkDopamine
METLIN ID64
PubChem Compound681
PDB IDNot Available
ChEBI ID18243
References
Synthesis ReferenceKlaus Schoellkopf, Rudolf Albrecht, Manfred Lehmann, Gertrud Schroeder, "Novel dopamine derivatives, processes for their preparation, and their use as medicinal agents." U.S. Patent US4958026, issued February, 1972.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]