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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:59:03 UTC
NP-MRD IDNP0001334
Secondary Accession NumbersNone
Natural Product Identification
Common NameDopamine
DescriptionDopamine is a member of the catecholamine family of neurotransmitters 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, which plays a major role in reward-motivated behaviour. Dopamine has many other functions outside the brain. In blood vessels, dopamine inhibits norepinephrine release and acts as a vasodilator (at normal concentrations); in the kidneys, it increases sodium excretion and urine output; in the pancreas, it reduces insulin production; in the digestive system, it reduces gastrointestinal motility and protects intestinal mucosa; and in the immune system, it reduces the activity of lymphocytes. Parkinson's disease, a degenerative condition causing tremor and motor impairment, is caused by a loss of dopamine-secreting neurons in an area of the midbrain called the substantia nigra. There is evidence that schizophrenia involves altered levels of dopamine activity, and most antipsychotic drugs used to treat this are dopamine antagonists, which reduce dopamine activity. Attention deficit hyperactivity disorder, bipolar disorder, and addiction are also characterized by defects in dopamine production or metabolism. It has been suggested that animals derived their dopamine-synthesizing machinery from bacteria via horizontal gene transfer that may have occurred relatively late in evolutionary time. This is perhaps a result of the symbiotic incorporation of bacteria into eukaryotic cells that gave rise to mitochondria. Dopamine is elevated in the urine of people who consume bananas. When present in sufficiently high levels, dopamine can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of dopamine are associated with neuroblastoma, Costello syndrome, leukemia, phaeochromocytoma, aromatic L-amino acid decarboxylase deficiency, and Menkes disease (MNK). High levels of dopamine can lead to hyperactivity, insomnia, agitation and anxiety, depression, delusions, excessive salivation, nausea, and digestive problems.
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 Mass153.1784 Da
Monoisotopic Mass153.07898 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Acacia berlandieriKNApSAcK Database
Acacia rigidula Benth.KNApSAcK Database
Actaea racemosaKNApSAcK Database
Alangium lamarckiiKNApSAcK Database
Alangium salviifoliumKNApSAcK Database
Argemone mexicanaKNApSAcK Database
Aristolochia giganteaKNApSAcK Database
Berberis amurensisKNApSAcK Database
Berberis aquifoliumKNApSAcK Database
Berberis aristataKNApSAcK Database
Berberis thunbergiiKNApSAcK Database
Berberis vulgarisKNApSAcK Database
Berberis wilsoniaeKNApSAcK Database
Brassica olereaceaKNApSAcK Database
Caulophyllum thalicroidesKNApSAcK Database
Cephaelis acuminataKNApSAcK Database
Chelidonium majusKNApSAcK Database
Cissampelos pareiraKNApSAcK Database
Citrus sinensisKNApSAcK Database
Clematis parvilobaKNApSAcK Database
Cocculus diversifoliusKNApSAcK Database
Cocculus japonicusKNApSAcK Database
Coptis japonicaKNApSAcK Database
Corydalis cavaKNApSAcK Database
Cyclea barbataKNApSAcK Database
Cyclea peltataKNApSAcK Database
Cytisus copariusKNApSAcK Database
Cytisus scopariusKNApSAcK Database
Delphinium pentagynumKNApSAcK Database
Dicentra spectabilisKNApSAcK Database
Erythrina crista-galliKNApSAcK Database
Eschscholzia californicaKNApSAcK Database
Fumaria officinalisKNApSAcK Database
Glaucium flavumKNApSAcK Database
Gnetum montanumKNApSAcK Database
Hermidium alipesKNApSAcK Database
Hydrastis canadensisKNApSAcK Database
Hypecoum lactiflorumKNApSAcK Database
Lindera angustifoliaKNApSAcK Database
Lophophora diffusaKNApSAcK Database
Lophophora friciiKNApSAcK Database
Lophophora jourdanianaKNApSAcK Database
Lophophora williamsiiKNApSAcK Database
Lyallia kerguelensisKNApSAcK Database
Macleaya cordataKNApSAcK Database
Magnolia obovataKNApSAcK Database
Magnolia officinalisKNApSAcK Database
Mahonia aquifoliumKNApSAcK Database
Meconopsis cambricaKNApSAcK Database
Monodora junodiiKNApSAcK Database
Musa acuminataKNApSAcK Database
Musa sapientumKNApSAcK Database
Myrtillocactus geometrizansKNApSAcK Database
Opuntia acanthocarpaKNApSAcK Database
Opuntia cylindricaKNApSAcK Database
Opuntia echinocarpaKNApSAcK Database
Opuntia ficus-indicaKNApSAcK Database
Opuntia imbricataKNApSAcK Database
Opuntia spinosiorKNApSAcK Database
Papaver bracteatumKNApSAcK Database
Papaver rhoeasKNApSAcK Database
Papaver somniferumKNApSAcK Database
Pelecyphora aselliformisKNApSAcK Database
Pereskia corrugataKNApSAcK Database
Pereskia tamicanaKNApSAcK Database
Pereskiopsis scandensKNApSAcK Database
Persea americanaKNApSAcK Database
Phaseolus vulgarisKNApSAcK Database
Phellodendron chinensisKNApSAcK Database
Pisum sativumKNApSAcK Database
Plantago majorKNApSAcK Database
Portulaca grandifloraKNApSAcK Database
Psychotria burucanaKNApSAcK Database
Psychotria ipecacuanhaKNApSAcK Database
Psychotria klugiiKNApSAcK Database
Romneya coulteriKNApSAcK Database
Solanum esculentumKNApSAcK Database
Solanum lycopersicum L.KNApSAcK Database
Solanum melanogenaKNApSAcK Database
Solanum tuberosum L.KNApSAcK Database
Spinacia oleraceaKNApSAcK Database
Stenocereus beneckeiKNApSAcK Database
Stenocereus erucaKNApSAcK Database
Stenocereus stellatusKNApSAcK Database
Stenocereus treleaseiKNApSAcK Database
Stephania hernandifoliaKNApSAcK Database
Stephania tetrandraKNApSAcK Database
Thalictrum flavumKNApSAcK Database
Theobroma cacaoKNApSAcK Database
Tinospora cordifoliaKNApSAcK Database
Trichocereus pachanoiKNApSAcK Database
Trichocereus peruvianusKNApSAcK Database
Trichocereus spachianusKNApSAcK Database
Trichocereus strigosusKNApSAcK Database
Vicia fabaKNApSAcK Database
Xylopia parvifloraKNApSAcK Database
Zizyphus jujuba var. spinosaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point128 °CNot Available
Boiling Point216.26 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
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 Area66.48 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.25 m³·mol⁻¹ChemAxon
Polarizability16.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
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
Good Scents IDrw1696771
References
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 ]