Record Information
Version1.0
Creation Date2016-09-30 22:19:18 UTC
Update Date2020-06-04 18:58:57 UTC
BMDB IDBMDB0000073
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Myelin sheath
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Myelin sheath
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Milk
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal CortexExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal MedullaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified2 +/- 2 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000073
DrugBank IDDB00988
Phenol Explorer Compound IDNot Available
FooDB 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 ]

Enzymes

General function:
Involved in catechol O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol (By similarity).
Gene Name:
COMT
Uniprot ID:
A7MBI7
Molecular weight:
30485.0
Reactions
Dopamine + Guaiacol → 3-Methoxytyramine + Pyrocatecholdetails
General function:
Involved in copper ion binding
Specific function:
Conversion of dopamine to noradrenaline.
Gene Name:
DBH
Uniprot ID:
P15101
Molecular weight:
68141.0
Reactions
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Waterdetails
General function:
Involved in copper ion binding
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the initial and rate limiting step in the cascade of reactions leading to melanin production from tyrosine. In addition to hydroxylating tyrosine to DOPA (3,4-dihydroxyphenylalanine), also catalyzes the oxidation of DOPA to DOPA-quinone, and possibly the oxidation of DHI (5,6-dihydroxyindole) to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
Q8MIU0
Molecular weight:
60304.0
Reactions
Tyramine + Oxygen → Dopamine + Waterdetails
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21398
Molecular weight:
59758.0
Reactions
Dopamine + Water + Oxygen → 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P27718
Molecular weight:
54294.0
General function:
Carbohydrate transport and metabolism
Specific function:
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis.
Gene Name:
SLC18A2
Uniprot ID:
Q27963
Molecular weight:
55756.0
General function:
Involved in dopamine:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
P27922
Molecular weight:
75691.0
General function:
Not Available
Specific function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P20288
Molecular weight:
50672.0
General function:
Involved in dopamine receptor binding
Specific function:
Not Available
Gene Name:
NSG1
Uniprot ID:
Q08DZ1
Molecular weight:
20968.0
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
D5 dopamine receptor
Uniprot ID:
Q28919
Molecular weight:
7597.0
General function:
Involved in GTP binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q9TSC8
Molecular weight:
10097.0
General function:
Involved in dopamine receptor binding
Specific function:
Not Available
Gene Name:
CALY
Uniprot ID:
Q0VCJ9
Molecular weight:
24662.0
General function:
Involved in dopamine receptor activity
Specific function:
Not Available
Gene Name:
DRD4
Uniprot ID:
Q8WNT0
Molecular weight:
11933.0
General function:
Involved in dopamine receptor binding
Specific function:
Not Available
Gene Name:
NSG2
Uniprot ID:
Q0VCZ0
Molecular weight:
19028.0
General function:
Not Available
Specific function:
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
DRD5
Uniprot ID:
Q95137
Molecular weight:
19589.0
General function:
Involved in dopamine receptor activity
Specific function:
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
DRD1
Uniprot ID:
Q95136
Molecular weight:
49317.0