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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (24)transporters (4) Show 28 proteins XML

enzymes (24)transporters (4) Show 28 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:51 UTC

HMDB ID

HMDB0000073

Secondary Accession Numbers

HMDB00073
HMDB0060277
HMDB60277

Metabolite Identification

Common Name

Dopamine

Description

Dopamine 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. A study has shown that urinary dopamine is produced by Bacillus and Serratia (PMID: 24621061 )

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)ethylamine	ChEBI
3,4-Dihydroxyphenethylamine	ChEBI
3-Hydroxytyramine	ChEBI
4-(2-Aminoethyl)-1,2-benzenediol	ChEBI
4-(2-Aminoethyl)benzene-1,2-diol	ChEBI
4-(2-Aminoethyl)catechol	ChEBI
4-(2-Aminoethyl)pyrocatechol	ChEBI
Deoxyepinephrine	ChEBI
Dopamina	ChEBI
Dopaminum	ChEBI
Hydroxytyramin	ChEBI
Medopa	Kegg
3,4-Dihydroxyphenylethylamine	HMDB
4-(2-Aminoethyl)-pyrocatechol	HMDB
a-(3,4-Dihydroxyphenyl)-b-aminoethane	HMDB
alpha-(3,4-Dihydroxyphenyl)-beta-aminoethane	HMDB
Dopamin	HMDB
Dopastat	HMDB
Dophamine	HMDB
Dynatra	HMDB
Hydroxytyramine	HMDB
Intropin	HMDB
Oxytyramine	HMDB
Revivan	HMDB
3,4 Dihydroxyphenethylamine	HMDB
Hydrochloride, dopamine	HMDB
Dopamine hydrochloride	HMDB

Chemical Formula

C₈H₁₁NO₂

Average Molecular Weight

153.1784

Monoisotopic Molecular Weight

153.078978601

IUPAC Name

4-(2-aminoethyl)benzene-1,2-diol

Traditional Name

dopamine

CAS Registry Number

62-31-7

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 Key

VYFYYTLLBUKUHU-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Catecholamines 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

catecholamine (CHEBI:18243 )
Biogenic amines (C03758 )
Tyramine derivatives (C03758 )
Dopamine (C03758 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060277)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	135.357	30932474
[M-H]-	MetCCS_train_neg	129.515	30932474
[M+H]+	Baker	125.236	30932474
[M-H]-	Not Available	132.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000284
[M+H]+	Not Available	137.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000284

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.43 g/L	ALOGPS
logP	-0.4	ALOGPS
logP	0.03	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	9.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.25 m³·mol⁻¹	ChemAxon
Polarizability	16.21 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	131.829	31661259
DarkChem	[M-H]-	130.154	31661259
AllCCS	[M+H]+	133.866	32859911
AllCCS	[M-H]-	132.601	32859911
DeepCCS	[M+H]+	134.759	30932474
DeepCCS	[M-H]-	130.961	30932474
DeepCCS	[M-2H]-	168.689	30932474
DeepCCS	[M+Na]+	144.228	30932474
AllCCS	[M+H]+	133.9	32859911
AllCCS	[M+H-H2O]+	129.4	32859911
AllCCS	[M+NH4]+	138.0	32859911
AllCCS	[M+Na]+	139.2	32859911
AllCCS	[M-H]-	132.6	32859911
AllCCS	[M+Na-2H]-	134.0	32859911
AllCCS	[M+HCOO]-	135.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dopamine	NCCC1=CC(O)=C(O)C=C1	2713.4	Standard polar	33892256
Dopamine	NCCC1=CC(O)=C(O)C=C1	1778.9	Standard non polar	33892256
Dopamine	NCCC1=CC(O)=C(O)C=C1	1715.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dopamine,1TMS,isomer #1	C[Si](C)(C)OC1=CC(CCN)=CC=C1O	1642.9	Semi standard non polar	33892256
Dopamine,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CCN)C=C1O	1644.1	Semi standard non polar	33892256
Dopamine,1TMS,isomer #3	C[Si](C)(C)NCCC1=CC=C(O)C(O)=C1	1877.1	Semi standard non polar	33892256
Dopamine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN)C=C1O[Si](C)(C)C	1682.2	Semi standard non polar	33892256
Dopamine,2TMS,isomer #2	C[Si](C)(C)NCCC1=CC=C(O)C(O[Si](C)(C)C)=C1	1773.8	Semi standard non polar	33892256
Dopamine,2TMS,isomer #3	C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C(O)=C1	1786.3	Semi standard non polar	33892256
Dopamine,2TMS,isomer #4	C[Si](C)(C)N(CCC1=CC=C(O)C(O)=C1)[Si](C)(C)C	2027.2	Semi standard non polar	33892256
Dopamine,3TMS,isomer #1	C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1826.6	Semi standard non polar	33892256
Dopamine,3TMS,isomer #1	C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1896.2	Standard non polar	33892256
Dopamine,3TMS,isomer #1	C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1843.6	Standard polar	33892256
Dopamine,3TMS,isomer #2	C[Si](C)(C)OC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	1989.8	Semi standard non polar	33892256
Dopamine,3TMS,isomer #2	C[Si](C)(C)OC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2056.4	Standard non polar	33892256
Dopamine,3TMS,isomer #2	C[Si](C)(C)OC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2037.9	Standard polar	33892256
Dopamine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O	2016.0	Semi standard non polar	33892256
Dopamine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O	2061.3	Standard non polar	33892256
Dopamine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O	1986.9	Standard polar	33892256
Dopamine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2063.8	Semi standard non polar	33892256
Dopamine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2013.3	Standard non polar	33892256
Dopamine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	1841.9	Standard polar	33892256
Dopamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(CCN)=CC=C1O	1902.0	Semi standard non polar	33892256
Dopamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN)C=C1O	1912.1	Semi standard non polar	33892256
Dopamine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O)C(O)=C1	2096.1	Semi standard non polar	33892256
Dopamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN)C=C1O[Si](C)(C)C(C)(C)C	2170.2	Semi standard non polar	33892256
Dopamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2264.6	Semi standard non polar	33892256
Dopamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2288.8	Semi standard non polar	33892256
Dopamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCC1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C	2433.5	Semi standard non polar	33892256
Dopamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2527.0	Semi standard non polar	33892256
Dopamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2520.3	Standard non polar	33892256
Dopamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2254.5	Standard polar	33892256
Dopamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2676.6	Semi standard non polar	33892256
Dopamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2672.8	Standard non polar	33892256
Dopamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2350.4	Standard polar	33892256
Dopamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	2701.8	Semi standard non polar	33892256
Dopamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	2658.4	Standard non polar	33892256
Dopamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	2313.3	Standard polar	33892256
Dopamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2962.2	Semi standard non polar	33892256
Dopamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2769.3	Standard non polar	33892256
Dopamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2312.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dopamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-1900000000-117a1a7207245f5377e7	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dopamine GC-MS (4 TMS)	splash10-00di-1900000000-8b7dcae82868308513da	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dopamine GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-117a1a7207245f5377e7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dopamine GC-MS (Non-derivatized)	splash10-00di-1900000000-8b7dcae82868308513da	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-8900000000-752bc8c11fa321b8a7ac	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (2 TMS) - 70eV, Positive	splash10-0089-9280000000-c894c19dda88ac048dd4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00e9-8900000000-88acdc978fe4a64e0fc5	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0uxu-4900000000-ff51177ebcb89b8c956c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-9200000000-a554eb700a06cecb8292	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014l-9000000000-db9813e1025f237a549b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0udi-0900000000-27e0d71db6d14d79759c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0uk9-0900000000-f1cf97c0d0dd509e229e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-00di-0900000000-aa09a2411e287abe74ed	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-00di-1900000000-97c42b109cab2005373d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-006x-9700000000-974bd18febffcceea2d6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0f79-0900000000-099173d4201beca9e548	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-000i-1900000000-9dc09f2661247c9d84b0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0006-9300000000-8b85fa9aac1ffb4c2873	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-0006-9000000000-9ea16d2057010279d433	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-014l-9000000000-32ca2db8fe2b4729ab94	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0f79-0900000000-ff587935c79b4592ffcf	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-000i-1900000000-8a35d8a2241bc18d6c50	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0006-9300000000-356a4b8f268863c7893e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-0006-9000000000-a88c1004f357858fbc6c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-014l-9000000000-271874005dcb90288512	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dopamine LC-ESI-QFT , negative-QTOF	splash10-0udi-0900000000-cfa7e1cb9f02ffb4447d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 10V, Positive-QTOF	splash10-0udr-0900000000-4e409c6edda911de39fe	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 20V, Positive-QTOF	splash10-000i-1900000000-90aa0e0866454c2eacc7	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 40V, Positive-QTOF	splash10-1000-9400000000-210fd696305d8cf76164	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 10V, Negative-QTOF	splash10-0udi-0900000000-ff95007680e484d3c57e	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 20V, Negative-QTOF	splash10-0udi-1900000000-6dcfecebbd98220ef746	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 40V, Negative-QTOF	splash10-0kil-6900000000-f476cfd569c441bc84aa	2017-06-28	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Brain
Epidermis
Fibroblasts
Kidney
Neuron
Pancreas
Placenta
Platelet
Skeletal Muscle
Spleen
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Tyrosine metabolism	Not Available
Aromatic L-Aminoacid Decarboxylase Deficiency		Not Available
Tyrosine hydroxylase deficiency		Not Available
Alkaptonuria		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	< 0.00013 uM	Adult (>18 years old)	Both	Normal	Emedicine	details
Blood	Detected and Quantified	0.00000-0.00013 uM	Adult (>18 years old)	Both	Normal	Emedicine	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.002+/-0.002 uM	Adult (>18 years old)	Both	Normal	12834252	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0059 +/- 0.002 uM	Elderly (>65 years old)	Both	Normal	10494443	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0045 +/- 0.0026 uM	Adult (>18 years old)	Both	Normal	10494443	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Urine	Detected and Quantified	0.5024 +/- 0.2337 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.107 (0.043-0.172) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15080725	details
Urine	Detected and Quantified	0.84 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	21670092	details
Urine	Detected and Quantified	0.22 +/- 0.07 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12622787	details
Urine	Detected and Quantified	0.44 +/- 0.13 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	12622787	details
Urine	Detected and Quantified	0.86 (0.179-1.541) umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	16288991	details
Urine	Detected and Quantified	2.626 (0.030-5.221) umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	16288991	details
Urine	Detected and Quantified	0.29 +/- 0.02 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.102 (0.0673-0.163) umol/mmol creatinine	Not Specified	Not Specified	Normal	Geigy Scientific ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25729574	details
Urine	Detected and Quantified	0.4 (0.2-0.7) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.13-2.63 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	1.31 +/- 0.76 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	1.1 +/- 0.7 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	0.200-5.220 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	9686366	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.261-1.697 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	23363473	details
Urine	Detected and Quantified	0.10 (0.066-0.16) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	>0.000650 uM	Adult (>18 years old)	Not Specified	Dopamine Beta-Hydroxylase Deficiency	GeneReviews:...	details
Blood	Detected and Quantified	18.0284 +/- 2.4552 uM	Elderly (>65 years old)	Both	Alzheimer's disease	17031479	details
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	4031843	details
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	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000392 uM	Adult (>18 years old)	Not Specified	Haemorrhagic infarction	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000510 uM	Adult (>18 years old)	Not Specified	Bacterial meningitis	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000810 uM	Adult (>18 years old)	Not Specified	Leucemic meningiosa	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000287 uM	Adult (>18 years old)	Not Specified	Encephalitis	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.34 +/- 0.10 uM	Adult (>18 years old)	Both	Alzheimer's disease	17031479	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00002 +/- 0.000006 uM	Adult (>18 years old)	Both	Hypothyroidism	9849813	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000021 (0.000015-0.000027) uM	Adult (>18 years old)	Both	Hypothyroidism	9849813	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000078 (0.0000065-0.00015) uM	Adult (>18 years old)	Both	Alzheimer's disease	10494443	details
Urine	Detected and Quantified	0.5565 +/- 0.3993 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.6381 +/- 0.2948 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	0.49 +/- 0.06 umol/mmol creatinine	Infant (0-1 year old)	Both	Vitiligo	12622787	details
Urine	Detected and Quantified	0.37 +/- 0.03 umol/mmol creatinine	Children (1-13 years old)	Both	Vitiligo	12622787	details
Urine	Detected and Quantified	0.4 +/- 0.05 umol/mmol creatinine	Children (1-13 years old)	Both	Vitiligo	12622787	details
Urine	Detected and Quantified	2426 +/- 0 nmol/mmol creatinine	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	16288991	details
Urine	Detected and Quantified	3.119 +/- 0 umol/mmol creatinine	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	16288991	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	25729574	details
Urine	Detected and Quantified	0.124 umol/mmol creatinine	Adolescent (13-18 years old)	Female	Dopamine-serotonin Vesicular Transport Defect	23363473	details
Urine	Detected and Quantified	2.7 umol/mmol creatinine	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details
Urine	Detected and Quantified	3.91 umol/mmol creatinine	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details

Associated Disorders and Diseases

Disease References

Dopamine Beta-Hydroxylase Deficiency
GeneReviews: Dopamine Beta-Hydroxylase Deficiency [Link]
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 ]
Cerebral infarction
Ratge D, Bauersfeld W, Wisser H: The relationship of free and conjugated catecholamines in plasma and cerebrospinal fluid in cerebral and meningeal disease. J Neural Transm. 1985;62(3-4):267-84. [PubMed:4031843 ]
Bacterial meningitis
Ratge D, Bauersfeld W, Wisser H: The relationship of free and conjugated catecholamines in plasma and cerebrospinal fluid in cerebral and meningeal disease. J Neural Transm. 1985;62(3-4):267-84. [PubMed:4031843 ]
Encephalitis
Ratge D, Bauersfeld W, Wisser H: The relationship of free and conjugated catecholamines in plasma and cerebrospinal fluid in cerebral and meningeal disease. J Neural Transm. 1985;62(3-4):267-84. [PubMed:4031843 ]
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 ]
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 ] Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Schizophrenia
Fryar-Williams S, Strobel JE: Biomarkers of a five-domain translational substrate for schizophrenia and schizoaffective psychosis. Biomark Res. 2015 Feb 6;3:3. doi: 10.1186/s40364-015-0028-1. eCollection 2015. [PubMed:25729574 ]
Dopamine-serotonin Vesicular Transport Defect
Rilstone JJ, Alkhater RA, Minassian BA: Brain dopamine-serotonin vesicular transport disease and its treatment. N Engl J Med. 2013 Feb 7;368(6):543-50. doi: 10.1056/NEJMoa1207281. Epub 2013 Jan 30. [PubMed:23363473 ]

Associated OMIM IDs

223360 (Dopamine Beta-Hydroxylase Deficiency)
104300 (Alzheimer's disease)
193200 (Vitiligo)
608643 (Aromatic L-amino acid decarboxylase deficiency)
610247 (Eosinophilic esophagitis)
181500 (Schizophrenia)

External Links

DrugBank ID

DB00988

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

681

PDB ID

Not Available

ChEBI ID

18243

Food Biomarker Ontology

Not Available

VMH ID

DOPA

MarkerDB ID

MDB00000039

Good Scents ID

Not Available

References

Synthesis Reference

Klaus 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

Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed: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. [PubMed: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. [PubMed: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. [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 ]
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 ]
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 ]
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 ]
Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
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 ]
Giuliano F, Allard J: Dopamine and sexual function. Int J Impot Res. 2001 Aug;13 Suppl 3:S18-28. [PubMed:11477488 ]
Giuliano F, Allard J: Dopamine and male sexual function. Eur Urol. 2001 Dec;40(6):601-8. [PubMed: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. [PubMed: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. [PubMed:17237217 ]
Mezzelani A, Landini M, Facchiano F, Raggi ME, Villa L, Molteni M, De Santis B, Brera C, Caroli AM, Milanesi L, Marabotti A: Environment, dysbiosis, immunity and sex-specific susceptibility: a translational hypothesis for regressive autism pathogenesis. Nutr Neurosci. 2015 May;18(4):145-61. doi: 10.1179/1476830513Y.0000000108. Epub 2014 Jan 21. [PubMed:24621061 ]

Only showing the first 10 proteins. There are 28 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Reactions

Tyramine + Oxygen + NADH + Hydrogen Ion → Dopamine + NAD + Water	details

Enzyme Details

2. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
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. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

Dopamine + Water + Oxygen → 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide	details

References

Bortolato M, Chen K, Shih JC: Monoamine oxidase inactivation: from pathophysiology to therapeutics. Adv Drug Deliv Rev. 2008 Oct-Nov;60(13-14):1527-33. doi: 10.1016/j.addr.2008.06.002. Epub 2008 Jul 4. [PubMed:18652859 ]
Kaludercic N, Carpi A, Menabo R, Di Lisa F, Paolocci N: Monoamine oxidases (MAO) in the pathogenesis of heart failure and ischemia/reperfusion injury. Biochim Biophys Acta. 2011 Jul;1813(7):1323-32. doi: 10.1016/j.bbamcr.2010.09.010. Epub 2010 Sep 24. [PubMed:20869994 ]

Enzyme Details

3. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
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:: P21397
Molecular weight:: 59681.27

Reactions

Dopamine + Water + Oxygen → 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide	details

References

Bortolato M, Chen K, Shih JC: Monoamine oxidase inactivation: from pathophysiology to therapeutics. Adv Drug Deliv Rev. 2008 Oct-Nov;60(13-14):1527-33. doi: 10.1016/j.addr.2008.06.002. Epub 2008 Jul 4. [PubMed:18652859 ]
Kaludercic N, Carpi A, Menabo R, Di Lisa F, Paolocci N: Monoamine oxidases (MAO) in the pathogenesis of heart failure and ischemia/reperfusion injury. Biochim Biophys Acta. 2011 Jul;1813(7):1323-32. doi: 10.1016/j.bbamcr.2010.09.010. Epub 2010 Sep 24. [PubMed:20869994 ]
Volavka J, Bilder R, Nolan K: Catecholamines and aggression: the role of COMT and MAO polymorphisms. Ann N Y Acad Sci. 2004 Dec;1036:393-8. [PubMed:15817751 ]

Enzyme Details

4. Dopamine beta-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of dopamine to noradrenaline.
Gene Name:: DBH
Uniprot ID:: P09172
Molecular weight:: 69064.45

Reactions

Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Water	details
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Water	details

References

Goldman JM, Cooper RL, Murr AS: Reproductive functions and hypothalamic catecholamines in response to the soil fumigant metam sodium: adaptations to extended exposures. Neurotoxicol Teratol. 2007 May-Jun;29(3):368-76. Epub 2006 Dec 6. [PubMed:17258889 ]
Arboleda G, Huang TJ, Waters C, Verkhratsky A, Fernyhough P, Gibson RM: Insulin-like growth factor-1-dependent maintenance of neuronal metabolism through the phosphatidylinositol 3-kinase-Akt pathway is inhibited by C2-ceramide in CAD cells. Eur J Neurosci. 2007 May;25(10):3030-8. [PubMed:17561816 ]
Garland EM, Black BK, Harris PA, Robertson D: Dopamine-beta-hydroxylase in postural tachycardia syndrome. Am J Physiol Heart Circ Physiol. 2007 Jul;293(1):H684-90. [PubMed:17625104 ]
Pyatskowit JW, Prohaska JR: Rodent brain and heart catecholamine levels are altered by different models of copper deficiency. Comp Biochem Physiol C Toxicol Pharmacol. 2007 Mar;145(2):275-81. Epub 2007 Jan 12. [PubMed:17287146 ]
LeBlanc J, Ducharme MB: Plasma dopamine and noradrenaline variations in response to stress. Physiol Behav. 2007 Jun 8;91(2-3):208-11. Epub 2007 Mar 2. [PubMed:17433386 ]

Enzyme Details

5. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
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.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

S-Adenosylmethionine + Dopamine → S-Adenosylhomocysteine + 3-Methoxytyramine	details

References

Ittiwut R, Listman JB, Ittiwut C, Cubells JF, Weiss RD, Brady K, Oslin D, Farrer LA, Kranzler HR, Gelernter J: Association between polymorphisms in catechol-O-methyltransferase (COMT) and cocaine-induced paranoia in European-American and African-American populations. Am J Med Genet B Neuropsychiatr Genet. 2011 Sep;156B(6):651-60. doi: 10.1002/ajmg.b.31205. Epub 2011 Jun 8. [PubMed:21656904 ]
Boot E, Booij J, Abeling N, Meijer J, da Silva Alves F, Zinkstok J, Baas F, Linszen D, van Amelsvoort T: Dopamine metabolism in adults with 22q11 deletion syndrome, with and without schizophrenia--relationship with COMT Val(1)(0)(8)/(1)(5)(8)Met polymorphism, gender and symptomatology. J Psychopharmacol. 2011 Jul;25(7):888-95. doi: 10.1177/0269881111400644. Epub 2011 Mar 29. [PubMed:21447540 ]
Volavka J, Bilder R, Nolan K: Catecholamines and aggression: the role of COMT and MAO polymorphisms. Ann N Y Acad Sci. 2004 Dec;1036:393-8. [PubMed:15817751 ]

Enzyme Details

6. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
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:: P20711
Molecular weight:: 53893.755

Reactions

L-Dopa → Dopamine + CO(2)	details
L-Dopa → Dopamine + Carbon dioxide	details

Enzyme Details

7. Amiloride-sensitive amine oxidase [copper-containing]

General function:: Involved in copper ion binding
Specific function:: Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:: ABP1
Uniprot ID:: P19801
Molecular weight:: 85377.1

Enzyme Details

8. Membrane primary amine oxidase

General function:: Involved in copper ion binding
Specific function:: Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:: AOC3
Uniprot ID:: Q16853
Molecular weight:: 84621.27

Reactions

Dopamine + Water + Oxygen → 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

9. Retina-specific copper amine oxidase

General function:: Involved in copper ion binding
Specific function:: Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:: AOC2
Uniprot ID:: O75106
Molecular weight:: 80515.11

Reactions

Dopamine + Water + Oxygen → 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

10. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

References

Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873 ]
Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528 ]

Enzyme Details

2. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]
Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]
Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
Busch AE, Quester S, Ulzheimer JC, Gorboulev V, Akhoundova A, Waldegger S, Lang F, Koepsell H: Monoamine neurotransmitter transport mediated by the polyspecific cation transporter rOCT1. FEBS Lett. 1996 Oct 21;395(2-3):153-6. [PubMed:8898084 ]
Breidert T, Spitzenberger F, Grundemann D, Schomig E: Catecholamine transport by the organic cation transporter type 1 (OCT1). Br J Pharmacol. 1998 Sep;125(1):218-24. [PubMed:9776363 ]

Enzyme Details

3. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]
Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]
Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
Busch AE, Karbach U, Miska D, Gorboulev V, Akhoundova A, Volk C, Arndt P, Ulzheimer JC, Sonders MS, Baumann C, Waldegger S, Lang F, Koepsell H: Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52. [PubMed:9687576 ]
Grundemann D, Koster S, Kiefer N, Breidert T, Engelhardt M, Spitzenberger F, Obermuller N, Schomig E: Transport of monoamine transmitters by the organic cation transporter type 2, OCT2. J Biol Chem. 1998 Nov 20;273(47):30915-20. [PubMed:9812985 ]
Verhaagh S, Schweifer N, Barlow DP, Zwart R: Cloning of the mouse and human solute carrier 22a3 (Slc22a3/SLC22A3) identifies a conserved cluster of three organic cation transporters on mouse chromosome 17 and human 6q26-q27. Genomics. 1999 Jan 15;55(2):209-18. [PubMed:9933568 ]

Enzyme Details

4. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]

Only showing the first 10 proteins. There are 28 proteins in total.

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Showing metabocard for Dopamine (HMDB0000073)

MOL for HMDB0000073 (Dopamine)

3D MOL for HMDB0000073 (Dopamine)

3D SDF for HMDB0000073 (Dopamine)

3D-SDF for HMDB0000073 (Dopamine)

PDB for HMDB0000073 (Dopamine)

3D PDB for HMDB0000073 (Dopamine)

SMILES for HMDB0000073 (Dopamine)

INCHI for HMDB0000073 (Dopamine)

Structure for HMDB0000073 (Dopamine)

3D Structure for HMDB0000073 (Dopamine)

Experimental Collision Cross Sections

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