Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:51 UTC
HMDB IDHMDB00073
Secondary Accession NumbersNone
Metabolite Identification
Common NameDopamine
DescriptionDopamine is a member of the catecholamine (Neurotransmitters) family in the brain, and is a precursor to epinephrine (adrenaline) and norepinephrine (noradrenaline). Dopamine is synthesized in the body (mainly by nervous tissue and adrenal glands) first by the hydration of the amino acid tyrosine to DOPA by tyrosine hydroxylase and then by the decarboxylation of DOPA by aromatic-L-amino-acid decarboxylase. Dopamine is a major transmitter in the extrapyramidal system of the brain, and important in regulating movement. A family of receptors (Dopamine receptors) mediates its action. --PubChem.
Structure
Thumb
Synonyms
  1. 2-(3,4-Dihydroxyphenyl)ethylamine
  2. 3,4-Dihydroxyphenethylamine
  3. 3,4-Dihydroxyphenylethylamine
  4. 3-Hydroxytyramine
  5. 4-(2-Aminoethyl)-1,2-benzenediol
  6. 4-(2-Aminoethyl)-Pyrocatechol
  7. 4-(2-Aminoethyl)catechol
  8. 4-(2-Aminoethyl)pyrocatechol
  9. a-(3,4-Dihydroxyphenyl)-b-aminoethane
  10. alpha-(3,4-Dihydroxyphenyl)-beta-aminoethane
  11. Deoxyepinephrine
  12. Dopamin
  13. Dopamine
  14. Dopaminum
  15. Dopastat
  16. Dophamine
  17. Dynatra
  18. Hydroxytyramin
  19. Hydroxytyramine
  20. Intropin
  21. Oxytyramine
  22. Revivan
Chemical FormulaC8H11NO2
Average Molecular Weight153.1784
Monoisotopic Molecular Weight153.078978601
IUPAC Name4-(2-aminoethyl)benzene-1,2-diol
Traditional IUPAC Namedopamine
CAS Registry Number62-31-7
SMILES
NCCC1=CC=C(O)C(O)=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
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassBenzenediols
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Biogenic amines(KEGG)
  • Dopamine(KEGG)
  • Tyramine derivatives(KEGG)
  • catecholamine(ChEBI)
Substituents
  • 1,2 Diphenol
  • Phenethylamine
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentCatecholamines and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Tyrosine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
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
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 area66.48ChemAxon
rotatable bond count2ChemAxon
refractivity43.25ChemAxon
polarizability16.21ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Kidney
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
  • Striatum
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Catecholamine BiosynthesisSMP00012map00350
Tyrosine MetabolismSMP00006map00350
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified22.50 +/- 4.50 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.002+/-0.002 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.0059 +/- 0.002 uMElderly (>65 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.0045 +/- 0.0026 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.107 (0.043-0.172) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified0.22 +/- 0.07 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified0.44 +/- 0.13 umol/mmol creatinineAdolescent (13-18 years old)BothNormal
UrineDetected and Quantified860 (179-1541) nmol/mmol creatinineInfant (0-1 year old)Not SpecifiedCommentNormal
UrineDetected and Quantified2626 (30-5221) nmol/mmol creatinineInfant (0-1 year old)Not SpecifiedCommentNormal
UrineDetected and Quantified0.4 (0.2-0.7) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified0.10 (0.066-0.16) umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified18.0284 +/- 2.4552 uMElderly (>65 years old)BothAlzheimer's disease
Cerebrospinal Fluid (CSF)Detected and Quantified0.000268 +/- 0.000124 uMAdult (>18 years old)Not SpecifiedCerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value
Cerebrospinal Fluid (CSF)Detected and Quantified0.000300 uMAdult (>18 years old)Not SpecifiedCerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value but renal insufficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.000392 uMAdult (>18 years old)Not SpecifiedHaemorrhagic infraction
Cerebrospinal Fluid (CSF)Detected and Quantified0.000510 uMAdult (>18 years old)Not SpecifiedBacterial meningitis
Cerebrospinal Fluid (CSF)Detected and Quantified0.000810 uMAdult (>18 years old)Not SpecifiedLeucemic meningiosa
Cerebrospinal Fluid (CSF)Detected and Quantified0.000287 uMAdult (>18 years old)Not SpecifiedEncephalitis
Cerebrospinal Fluid (CSF)Detected and Quantified0.34 +/- 0.10 uMAdult (>18 years old)BothAlzheimer's disease
Cerebrospinal Fluid (CSF)Detected and Quantified0.00002 +/- 0.000006 uMAdult (>18 years old)BothHypothyroidism
Cerebrospinal Fluid (CSF)Detected and Quantified0.000021 (0.000015-0.000027) uMAdult (>18 years old)BothHypothyroidism
Cerebrospinal Fluid (CSF)Detected and Quantified0.000078 (0.0000065-0.00015) uMAdult (>18 years old)BothAlzheimer's disease
UrineDetected and Quantified0.49 +/- 0.06 umol/mmol creatinineInfant (0-1 year old)BothVitiligo
UrineDetected and Quantified0.37 +/- 0.03 umol/mmol creatinineChildren (1-13 year old)BothCommentVitiligo
UrineDetected and Quantified0.4 +/- 0.05 umol/mmol creatinineChildren (1-13 year old)BothCommentVitiligo
UrineDetected and Quantified2426 +/- 0 nmol/mmol creatinineInfant (0-1 year old)MaleCommentAromatic L-amino acid decarboxylase deficiency
UrineDetected and Quantified3119 +/- 0 nmol/mmol creatinineInfant (0-1 year old)MaleCommentAromatic L-amino acid decarboxylase deficiency
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  • Raskind MA, Peskind ER, Holmes C, Goldstein DS: Patterns of cerebrospinal fluid catechols support increased central noradrenergic responsiveness in aging and Alzheimer's disease. Biol Psychiatry. 1999 Sep 15;46(6):756-65. Pubmed: 10494443
  • Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479
Aromatic L-amino acid decarboxylase deficiency
  • Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. Pubmed: 16288991
Hypothyroidism
  • Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. Pubmed: 9849813
Vitiligo
  • Cucchi ML, Frattini P, Santagostino G, Preda S, Orecchia G: Catecholamines increase in the urine of non-segmental vitiligo especially during its active phase. Pigment Cell Res. 2003 Apr;16(2):111-6. Pubmed: 12622787
Associated OMIM IDs
DrugBank IDDB00988
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012163
KNApSAcK IDC00001408
Chemspider ID661
KEGG Compound IDC03758
BioCyc IDDOPAMINE
BiGG ID42467
Wikipedia LinkDopamine
NuGOwiki LinkHMDB00073
Metagene LinkHMDB00073
METLIN ID64
PubChem Compound681
PDB IDLDP
ChEBI ID18243
References
Synthesis ReferenceBudnik, Josef. 2-(3,4-Dihydroxyphenyl)ethylamine hydrochloride. Czech. (1986), 2 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. Pubmed: 6085021
  2. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. Pubmed: 12649306
  3. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252
  4. Raskind MA, Peskind ER, Holmes C, Goldstein DS: Patterns of cerebrospinal fluid catechols support increased central noradrenergic responsiveness in aging and Alzheimer's disease. Biol Psychiatry. 1999 Sep 15;46(6):756-65. Pubmed: 10494443
  5. Mannelli M, Ianni L, Lazzeri C, Castellani W, Pupilli C, La Villa G, Barletta G, Serio M, Franchi F: In vivo evidence that endogenous dopamine modulates sympathetic activity in man. Hypertension. 1999 Sep;34(3):398-402. Pubmed: 10489384
  6. Jiang H, Betancourt L, Smith RG: Ghrelin amplifies dopamine signaling by cross talk involving formation of growth hormone secretagogue receptor/dopamine receptor subtype 1 heterodimers. Mol Endocrinol. 2006 Aug;20(8):1772-85. Epub 2006 Apr 6. Pubmed: 16601073
  7. Brody AL, Mandelkern MA, Olmstead RE, Scheibal D, Hahn E, Shiraga S, Zamora-Paja E, Farahi J, Saxena S, London ED, McCracken JT: Gene variants of brain dopamine pathways and smoking-induced dopamine release in the ventral caudate/nucleus accumbens. Arch Gen Psychiatry. 2006 Jul;63(7):808-16. Pubmed: 16818870
  8. Bauman A: Unilateral adrenal catecholamine excess. Pheochromocytoma or possible sporadic medullary hyperplasia. Arch Intern Med. 1982 Feb;142(2):377-8. Pubmed: 7059264
  9. King BM: The rise, fall, and resurrection of the ventromedial hypothalamus in the regulation of feeding behavior and body weight. Physiol Behav. 2006 Feb 28;87(2):221-44. Epub 2006 Jan 18. Pubmed: 16412483
  10. Cucchi ML, Frattini P, Santagostino G, Preda S, Orecchia G: Catecholamines increase in the urine of non-segmental vitiligo especially during its active phase. Pigment Cell Res. 2003 Apr;16(2):111-6. Pubmed: 12622787
  11. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. Pubmed: 9849813
  12. Kobayashi K, Yasuhara T, Agari T, Muraoka K, Kameda M, Ji Yuan W, Hayase H, Matsui T, Miyoshi Y, Shingo T, Date I: Control of dopamine-secretion by Tet-Off system in an in vivo model of parkinsonian rat. Brain Res. 2006 Aug 2;1102(1):1-11. Epub 2006 Jun 27. Pubmed: 16806124
  13. Schenarts PJ, Sagraves SG, Bard MR, Toschlog EA, Goettler CE, Newell MA, Rotondo MF: Low-dose dopamine: a physiologically based review. Curr Surg. 2006 May-Jun;63(3):219-25. Pubmed: 16757377
  14. Piazza O, Zito G, Valente A, Tufano R: Effects of dopamine infusion on forearm blood flow in critical patients. Med Sci Monit. 2006 Feb;12(2):CR90-3. Epub 2006 Jan 26. Pubmed: 16449954
  15. Wang HY, Xiao Y, Han J, Chang XS: Simultaneous determination of dopamine and carvedilol in human serum and urine by first-order derivative fluorometry. Anal Sci. 2005 Nov;21(11):1281-5. Pubmed: 16317894
  16. Elchisak MA, Carlson JH: Assay of free and conjugated catecholamines by high-performance liquid chromatography with electrochemical detection. J Chromatogr. 1982 Dec 10;233:79-88. Pubmed: 7161364
  17. Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. Pubmed: 8884658
  18. Kopieniak M, Wieczorkiewicz-Plaza A, Maciejewski R: Dopamine activity changes in cerebral cortex in the course of experimental acute pancreatitis. Ann Univ Mariae Curie Sklodowska [Med]. 2004;59(1):382-6. Pubmed: 16146016
  19. Nikolelis DP, Drivelos DA, Simantiraki MG, Koinis S: An optical spot test for the detection of dopamine in human urine using stabilized in air lipid films. Anal Chem. 2004 Apr 15;76(8):2174-80. Pubmed: 15080725
  20. Eisenhofer G, Aneman A, Friberg P, Hooper D, Fandriks L, Lonroth H, Hunyady B, Mezey E: Substantial production of dopamine in the human gastrointestinal tract. J Clin Endocrinol Metab. 1997 Nov;82(11):3864-71. Pubmed: 9360553
  21. Berridge KC, Robinson TE: What is the role of dopamine in reward: hedonic impact, reward learning, or incentive salience? Brain Res Brain Res Rev. 1998 Dec;28(3):309-69. Pubmed: 9858756
  22. Giuliano F, Allard J: Dopamine and sexual function. Int J Impot Res. 2001 Aug;13 Suppl 3:S18-28. Pubmed: 11477488
  23. Giuliano F, Allard J: Dopamine and male sexual function. Eur Urol. 2001 Dec;40(6):601-8. Pubmed: 11805404
  24. Pecina S, Cagniard B, Berridge KC, Aldridge JW, Zhuang X: Hyperdopaminergic mutant mice have higher "wanting" but not "liking" for sweet rewards. J Neurosci. 2003 Oct 15;23(28):9395-402. Pubmed: 14561867
  25. Barron AB, Maleszka R, Vander Meer RK, Robinson GE: Octopamine modulates honey bee dance behavior. Proc Natl Acad Sci U S A. 2007 Jan 30;104(5):1703-7. Epub 2007 Jan 19. Pubmed: 17237217

Enzymes

Gene Name:
TYR
Uniprot ID:
P14679
Reactions
Tyramine + Oxygen + NADH + Hydrogen Ion unknown Dopamine + NAD + Waterdetails
Gene Name:
MAOB
Uniprot ID:
P27338
Reactions
Dopamine + Water + Oxygen unknown 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Gene Name:
MAOA
Uniprot ID:
P21397
Reactions
Dopamine + Water + Oxygen unknown 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Gene Name:
DBH
Uniprot ID:
P09172
Reactions
Dopamine + Ascorbic acid + Oxygen unknown xi-Norepinephrine + Dehydroascorbic acid + Waterdetails
Dopamine + Ascorbic acid + Oxygen unknown Norepinephrine + Dehydroascorbic acid + Waterdetails
Gene Name:
COMT
Uniprot ID:
P21964
Reactions
S-Adenosylmethionine + Dopamine unknown S-Adenosylhomocysteine + 3-Methoxytyraminedetails
Gene Name:
DDC
Uniprot ID:
P20711
Reactions
L-Dopa unknown Dopamine + CO(2)details
L-Dopa unknown Dopamine + Carbon dioxidedetails
Gene Name:
AOC3
Uniprot ID:
Q16853
Reactions
Dopamine + Water + Oxygen unknown 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Gene Name:
AOC2
Uniprot ID:
O75106
Reactions
Dopamine + Water + Oxygen unknown 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
DRD2
Uniprot ID:
P14416
Gene Name:
DRD4
Uniprot ID:
P21917
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Gene Name:
CADPS2
Uniprot ID:
Q86UW7
Gene Name:
DRD3
Uniprot ID:
P35462
Gene Name:
DRD1
Uniprot ID:
P21728
Gene Name:
DRD5
Uniprot ID:
P21918
Gene Name:
dopamine D4 receptor
Uniprot ID:
Q99586
Gene Name:
dopamine D4 receptor
Uniprot ID:
Q99587

Transporters

Gene Name:
SLC22A5
Uniprot ID:
O76082
Gene Name:
SLC22A1
Uniprot ID:
O15245
Gene Name:
SLC22A2
Uniprot ID:
O15244
Gene Name:
SLC22A3
Uniprot ID:
O75751