Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2018-05-28 18:28:41 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 in a few different foods, such as swiss chards, oats, and red beetroots and in a lower concentration in ryes, saskatoon berries, and dills. Dopamine has also been detected, but not quantified in, several different foods, such as cocoa beans, custard apples, french plantains, garden tomato, and purslanes. 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
Bioavailability1ChemAxon
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 Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1900000000-117a1a7207245f5377e7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-1900000000-8b7dcae82868308513daView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-117a1a7207245f5377e7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1900000000-8b7dcae82868308513daView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-8900000000-752bc8c11fa321b8a7acView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-9280000000-c894c19dda88ac048dd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uxu-4900000000-ff51177ebcb89b8c956cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9200000000-a554eb700a06cecb8292View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-db9813e1025f237a549bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-27e0d71db6d14d79759cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0uk9-0900000000-f1cf97c0d0dd509e229eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-0900000000-aa09a2411e287abe74edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-1900000000-97c42b109cab2005373dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-006x-9700000000-974bd18febffcceea2d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0f79-0900000000-099173d4201beca9e548View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-9dc09f2661247c9d84b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9300000000-8b85fa9aac1ffb4c2873View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-9ea16d2057010279d433View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-9000000000-32ca2db8fe2b4729ab94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0f79-0900000000-ff587935c79b4592ffcfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-8a35d8a2241bc18d6c50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9300000000-356a4b8f268863c7893eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-a88c1004f357858fbc6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-9000000000-271874005dcb90288512View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0900000000-cfa7e1cb9f02ffb4447dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-4e409c6edda911de39feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-90aa0e0866454c2eacc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9400000000-210fd696305d8cf76164View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-ff95007680e484d3c57eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-6dcfecebbd98220ef746View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kil-6900000000-f476cfd569c441bc84aaView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00e9-8900000000-88acdc978fe4a64e0fc5View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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.