Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2019-11-26 03:06:18 UTC
Primary IDFDB012163
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 very strong basic compound (based on its pKa). Dopamine exists in all living organisms, ranging from bacteria to humans. Dopamine is found, on average, in the highest concentration within a few different foods, such as swiss chards, oats, and red beetroots and in a lower concentration in ryes, spinachs, and wheats. Dopamine has also been detected, but not quantified in, several different foods, such as cocoa beans, potato, purslanes, milk (cow), and eggplants. This could make dopamine a potential biomarker for the consumption of these foods. Dopamine is a potentially toxic compound.
CAS Number62-31-7
Structure
Thumb
Synonyms
SynonymSource
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
(3H)-Dopaminebiospider
1,2-Benzenediol, 4-(2-aminoethyl)- (9CI)biospider
3-Hydroxtyraminebiospider
4-(2-Aminoethyl)-1,2-benzenediol, 9CIdb_source
4-(2-aminoethyl)benzene-1,2-diolbiospider
ASL 279db_source
Cardiosterildb_source
NSC 169105db_source
Predicted Properties
PropertyValueSource
Water Solubility7.43 g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H11NO2
IUPAC name4-(2-aminoethyl)benzene-1,2-diol
InChI IdentifierInChI=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
Isomeric SMILESNCCC1=CC(O)=C(O)C=C1
Average Molecular Weight153.1784
Monoisotopic Molecular Weight153.078978601
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 62.73%; H 7.24%; N 9.14%; O 20.89%DFC
Melting Point128 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-0.98HANSCH,C ET AL. (1995)
Experimental pKa8.93
Isoelectric pointNot Available
Charge+1
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1900000000-117a1a7207245f5377e7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-1900000000-8b7dcae82868308513daJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-117a1a7207245f5377e7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1900000000-8b7dcae82868308513daJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-8900000000-752bc8c11fa321b8a7acJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-9280000000-c894c19dda88ac048dd4JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uxu-4900000000-ff51177ebcb89b8c956cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9200000000-a554eb700a06cecb8292JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-db9813e1025f237a549bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-27e0d71db6d14d79759cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0uk9-0900000000-f1cf97c0d0dd509e229eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-0900000000-aa09a2411e287abe74edJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-1900000000-97c42b109cab2005373dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-006x-9700000000-974bd18febffcceea2d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0f79-0900000000-099173d4201beca9e548JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-9dc09f2661247c9d84b0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9300000000-8b85fa9aac1ffb4c2873JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-9ea16d2057010279d433JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-9000000000-32ca2db8fe2b4729ab94JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0f79-0900000000-ff587935c79b4592ffcfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-8a35d8a2241bc18d6c50JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9300000000-356a4b8f268863c7893eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-a88c1004f357858fbc6cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-9000000000-271874005dcb90288512JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0900000000-cfa7e1cb9f02ffb4447dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-4e409c6edda911de39feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-90aa0e0866454c2eacc7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9400000000-210fd696305d8cf76164JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-ff95007680e484d3c57eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-6dcfecebbd98220ef746JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kil-6900000000-f476cfd569c441bc84aaJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00e9-8900000000-88acdc978fe4a64e0fc5JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID661
ChEMBL IDCHEMBL59
KEGG Compound IDC03758
Pubchem Compound ID681
Pubchem Substance IDNot Available
ChEBI ID18243
Phenol-Explorer IDNot Available
DrugBank IDDB00988
HMDB IDHMDB00073
CRC / DFC (Dictionary of Food Compounds) IDHDV99-C:HDV99-C
EAFUS IDNot Available
Dr. Duke ID3-HYDROXYTYRAMINE|DOPAMINE
BIGG ID42467
KNApSAcK IDC00001408
HET IDLDP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDopamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
adrenergic37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
anti lactagogueDUKE
anti myocontractantDUKE
anti neurogenicDUKE
anti Parkinsonian48407 A drug used in the treatment of Parkinson's disease.DUKE
anti prolactinDUKE
anti shockDUKE
anti thyreotropicDUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hypertensiveDUKE
inotropicDUKE
myocontractantDUKE
natriureticDUKE
neurotransmitter25512 An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.DUKE
priapisticDUKE
sympathomimetic35524 A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.DUKE
teratogenic50905 A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.DUKE
vasoconstrictor50514 Drug used to cause constriction of the blood vessels.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
dopaminergic48560 A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.CHEBI
Enzymes
NameGene NameUniProt ID
Aromatic-L-amino-acid decarboxylaseDDCP20711
D(2) dopamine receptorDRD2P14416
D(4) dopamine receptorDRD4P21917
Pathways
NameSMPDB LinkKEGG Link
Catecholamine BiosynthesisSMP00012 map00350
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.