2.0 2012-05-31 09:56:41 -0600 2015-06-03 15:53:10 -0600 ECMDB00073 M2MDB000026 Dopamine Dopamine is synthesized 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. 2-(3,4-Dihydroxyphenyl)ethylamine 3,4-Dihydroxyphenethylamine 3,4-Dihydroxyphenylethylamine 3-Hydroxytyramine 4-(2-Aminoethyl)-1,2-benzenediol 4-(2-Aminoethyl)-Pyrocatechol 4-(2-Aminoethyl)benzene-1,2-diol 4-(2-Aminoethyl)catechol 4-(2-Aminoethyl)pyrocatechol A-(3,4-Dihydroxyphenyl)-b-aminoethane Alpha-(3,4-Dihydroxyphenyl)-b-aminoethane Alpha-(3,4-Dihydroxyphenyl)-beta-aminoethane Deoxyepinephrine Dopamin Dopamine Dopaminum Dopastat Dophamine Dynatra Hydroxytyramin Hydroxytyramine Intropin Oxytyramine Revivan α-(3,4-Dihydroxyphenyl)-b-aminoethane α-(3,4-Dihydroxyphenyl)-β-aminoethane C8H11NO2 153.1784 153.078978601 4-(2-aminoethyl)benzene-1,2-diol dopamine 62-31-7 NCCC1=CC(O)=C(O)C=C1 InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2 VYFYYTLLBUKUHU-UHFFFAOYSA-N Solid Extra-organism Periplasm logp -0.40 ALOGPS logs -1.31 ALOGPS solubility 7.43e+00 g/l ALOGPS melting_point 128 oC logp 0.03 ChemAxon pka_strongest_acidic 10.01 ChemAxon pka_strongest_basic 9.27 ChemAxon iupac 4-(2-aminoethyl)benzene-1,2-diol ChemAxon average_mass 153.1784 ChemAxon mono_mass 153.078978601 ChemAxon smiles NCCC1=CC(O)=C(O)C=C1 ChemAxon formula C8H11NO2 ChemAxon inchi InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2 ChemAxon inchikey VYFYYTLLBUKUHU-UHFFFAOYSA-N ChemAxon polar_surface_area 66.48 ChemAxon refractivity 43.25 ChemAxon polarizability 16.21 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Tyrosine metabolism ec00350 Specdb::CMs 314 Specdb::CMs 1775 Specdb::CMs 5743 Specdb::CMs 30527 Specdb::CMs 30983 Specdb::CMs 37282 Specdb::CMs 159201 Specdb::CMs 1049628 Specdb::CMs 1049630 Specdb::CMs 1049632 Specdb::CMs 1049633 Specdb::CMs 1049635 Specdb::CMs 1049637 Specdb::CMs 1049639 Specdb::CMs 1049640 Specdb::CMs 1049642 Specdb::CMs 1049644 Specdb::CMs 1049646 Specdb::CMs 1049648 Specdb::CMs 1049650 Specdb::EiMs 230 Specdb::NmrOneD 1070 Specdb::NmrOneD 142030 Specdb::NmrOneD 142031 Specdb::NmrOneD 142032 Specdb::NmrOneD 142033 Specdb::NmrOneD 142034 Specdb::NmrOneD 142035 Specdb::NmrOneD 142036 Specdb::NmrOneD 142037 Specdb::NmrOneD 142038 Specdb::NmrOneD 142039 Specdb::NmrOneD 142040 Specdb::NmrOneD 142041 Specdb::NmrOneD 142042 Specdb::NmrOneD 142043 Specdb::NmrOneD 142044 Specdb::NmrOneD 142045 Specdb::NmrOneD 142046 Specdb::NmrOneD 142047 Specdb::NmrOneD 142048 Specdb::NmrOneD 142049 Specdb::MsMs 120 Specdb::MsMs 121 Specdb::MsMs 122 Specdb::MsMs 2777 Specdb::MsMs 2778 Specdb::MsMs 2779 Specdb::MsMs 2780 Specdb::MsMs 2781 Specdb::MsMs 2782 Specdb::MsMs 2783 Specdb::MsMs 2784 Specdb::MsMs 2785 Specdb::MsMs 2786 Specdb::MsMs 2787 Specdb::MsMs 2788 Specdb::MsMs 2789 Specdb::MsMs 2790 Specdb::MsMs 2791 Specdb::MsMs 240376 Specdb::MsMs 240377 Specdb::MsMs 240378 Specdb::MsMs 242431 Specdb::MsMs 242432 Specdb::MsMs 242433 Specdb::MsMs 436587 Specdb::NmrTwoD 1128 HMDB00073 681 661 C03758 18243 DOPAMINE LDP Dopamine Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. 6085021 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. 12649306 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. 12834252 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. 10494443 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. 10489384 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. 16601073 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. 16818870 Bauman A: Unilateral adrenal catecholamine excess. Pheochromocytoma or possible sporadic medullary hyperplasia. Arch Intern Med. 1982 Feb;142(2):377-8. 7059264 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. 16412483 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. 12622787 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. 9849813 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. 16806124 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. 16757377 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. 16449954 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. 16317894 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. 7161364 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. 8884658 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. 16146016 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. 15080725 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. 9360553 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. 9858756 Giuliano F, Allard J: Dopamine and sexual function. Int J Impot Res. 2001 Aug;13 Suppl 3:S18-28. 11477488 Giuliano F, Allard J: Dopamine and male sexual function. Eur Urol. 2001 Dec;40(6):601-8. 11805404 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. 14561867 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. 17237217 Budnik, Josef. 2-(3,4-Dihydroxyphenyl)ethylamine hydrochloride. Czech. (1986), 2 pp. Primary amine oxidase P46883 AMO_ECOLI tynA http://ecmdb.ca/proteins/P46883.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Dopamine + Water + Oxygen > 3,4-Dihydroxyphenylacetaldehyde + Hydrogen peroxide + Ammonium Dopamine + Water + Oxygen <> 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide R04300