| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:51 -0700 |
| HMDB ID |
HMDB00073 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Dopamine |
| Description |
Dopamine 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 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)catechol
- 4-(2-Aminoethyl)pyrocatechol
- a-(3,4-Dihydroxyphenyl)-b-aminoethane
- alpha-(3,4-Dihydroxyphenyl)-beta-aminoethane
- Deoxyepinephrine
- Dopamin
- Dopamine
- Dopaminum
- Dopastat
- Dophamine
- Dynatra
- Hydroxytyramin
- Hydroxytyramine
- Intropin
- Oxytyramine
- Revivan
|
| Chemical Formula |
C8H11NO2 |
| Average Molecular Weight |
153.1784 |
| Monoisotopic Molecular Weight |
153.078978601 |
| IUPAC Name |
4-(2-aminoethyl)benzene-1,2-diol |
| Traditional IUPAC Name |
dopamine |
| CAS Registry Number |
62-31-7 |
| 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 Key |
VYFYYTLLBUKUHU-UHFFFAOYSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Homomonocyclic Compounds |
| Class |
Phenols and Derivatives |
| Sub Class |
Benzenediols |
| 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 Parent |
Catecholamines and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Tyrosine metabolism
|
| Application |
Not Available |
| Cellular locations |
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
128 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
535 mg/mL |
Not Available |
| LogP |
-0.98 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|
| Gas-MS Spectrum |
| 1H NMR Spectrum |
| MS/MS Spectrum Quattro_QQQ 10 |
| MS/MS Spectrum Quattro_QQQ 25 |
| MS/MS Spectrum Quattro_QQQ 40 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 |
| [1H,13C] 2D NMR Spectrum |
|
| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
|
| Tissue Location |
- Muscle
- Skeletal Muscle
- Bladder
- Fibroblasts
- Neuron
- Pancreas
- Placenta
- Testes
- Kidney
- Epidermis
- Brain
- Myelin
- Adrenal Gland
- Adipose Tissue
- Adrenal Cortex
- Adrenal Medulla
- Nerve Cells
- Platelet
- Spleen
- Striatum
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
22.50 +/- 4.50 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.002+/-0.002 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0059 +/- 0.002 uM |
Elderly (>65 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0045 +/- 0.0026 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.107 (0.043-0.172) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.22 +/- 0.07 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.44 +/- 0.13 umol/mmol creatinine |
Adolescent (13-18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
860 (179-1541) nmol/mmol creatinine |
Infant (0-1 year old) |
Not Specified |
Normal |
Free dopamine levels
|
| Urine |
Detected and Quantified |
|
2626 (30-5221) nmol/mmol creatinine |
Infant (0-1 year old) |
Not Specified |
Normal |
Total dopamine levels
|
| Urine |
Detected and Quantified |
|
0.4 (0.2-0.7) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
by LC-MS/MS (Biocrates kit)
|
| Urine |
Detected and Quantified |
|
0.10 (0.066-0.16) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
18.0284 +/- 2.4552 uM |
Elderly (>65 years old) |
Both |
Alzheimer's disease |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000268 +/- 0.000124 uM |
Adult (>18 years old) |
Not Specified |
Cerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000300 uM |
Adult (>18 years old) |
Not Specified |
Cerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value but renal insufficiency |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000392 uM |
Adult (>18 years old) |
Not Specified |
Haemorrhagic infraction |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000510 uM |
Adult (>18 years old) |
Not Specified |
Bacterial meningitis |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000810 uM |
Adult (>18 years old) |
Not Specified |
Leucemic meningiosa |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000287 uM |
Adult (>18 years old) |
Not Specified |
Encephalitis |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.34 +/- 0.10 uM |
Adult (>18 years old) |
Both |
Alzheimer's disease |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00002 +/- 0.000006 uM |
Adult (>18 years old) |
Both |
Hypothyroidism |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000021 (0.000015-0.000027) uM |
Adult (>18 years old) |
Both |
Hypothyroidism |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000078 (0.0000065-0.00015) uM |
Adult (>18 years old) |
Both |
Alzheimer's disease |
Not Available |
| Urine |
Detected and Quantified |
|
0.49 +/- 0.06 umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Vitiligo |
Not Available |
| Urine |
Detected and Quantified |
|
0.37 +/- 0.03 umol/mmol creatinine |
Children (1-13 year old) |
Both |
Vitiligo |
Age group: 1-5 years old
|
| Urine |
Detected and Quantified |
|
0.4 +/- 0.05 umol/mmol creatinine |
Children (1-13 year old) |
Both |
Vitiligo |
Age group: 6-10 years old
|
| Urine |
Detected and Quantified |
|
2426 +/- 0 nmol/mmol creatinine |
Infant (0-1 year old) |
Male |
Aromatic L-amino acid decarboxylase deficiency |
Free dopamine levels
|
| Urine |
Detected and Quantified |
|
3119 +/- 0 nmol/mmol creatinine |
Infant (0-1 year old) |
Male |
Aromatic L-amino acid decarboxylase deficiency |
Total dopamine levels
|
|
| Associated Disorders and Diseases |
| Disease References |
| 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
|
| 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
|
| 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
|
|
| Associated OMIM IDs |
- 104300
(Alzheimer's disease)
- 107930
(Aromatic L-amino acid decarboxylase deficiency)
- 218700
(Hypothyroidism)
- 193200
(Vitiligo)
|
| External Links |
| DrugBank ID |
DB00988  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB012163 |
| KNApSAcK ID |
C00001408  |
| Chemspider ID |
661  |
| KEGG Compound ID |
C03758  |
| BioCyc ID |
DOPAMINE  |
| BiGG ID |
42467  |
| Wikipedia Link |
Dopamine  |
| NuGOwiki Link |
HMDB00073  |
| Metagene Link |
HMDB00073  |
| METLIN ID |
64  |
| PubChem Compound |
681  |
| PDB ID |
LDP  |
| ChEBI ID |
18243  |
| References |
| Synthesis Reference |
Budnik, Josef. 2-(3,4-Dihydroxyphenyl)ethylamine hydrochloride. Czech. (1986), 2 pp. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- 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
- 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
- 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
- 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
- Bauman A: Unilateral adrenal catecholamine excess. Pheochromocytoma or possible sporadic medullary hyperplasia. Arch Intern Med. 1982 Feb;142(2):377-8.
Pubmed: 7059264
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9.
Pubmed: 6085021
- 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
- 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
|
| Enzymes |
|
|
|
|
| Name: |
Dopamine beta-hydroxylase
|
| Reactions: |
- 3,4-dihydroxyphenethylamine + ascorbate + O2 = noradrenaline + dehydroascorbate + H2O [RN:R02535]
|
| Gene Name: |
DBH |
| Uniprot ID: |
P09172  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
| Name: |
Aromatic-L-amino-acid decarboxylase
|
| Reactions: |
- (1) 3,4-dihydroxy-L-phenylalanine = dopamine + CO2 [RN:R02080]
- (2) 5-hydroxy-L-tryptophan = 5-hydroxytryptamine + CO2 [RN:R02701]
|
| Gene Name: |
DDC |
| Uniprot ID: |
P20711  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
| Name: |
Cytochrome P450 2C9
|
| Reactions: |
- (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
|
| Gene Name: |
CYP2C9 |
| Uniprot ID: |
P11712  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Cytochrome P450 2C19
|
| Reactions: |
- (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
|
| Gene Name: |
CYP2C19 |
| Uniprot ID: |
P33261  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Cytochrome P450 2D6
|
| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
|
| Gene Name: |
CYP2D6 |
| Uniprot ID: |
P10635  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Cytochrome P450 1A2
|
| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
|
| Gene Name: |
CYP1A2 |
| Uniprot ID: |
P05177  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|