ContaminantDB: Dopamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (18)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:17:08 UTC

Update Date

2026-05-14 16:55:05 UTC

Accession Number

CHEM003260

Identification

Common Name

Dopamine

Class

Small Molecule

Description

One of the catecholamine neurotransmitters in the brain. It is derived from tyrosine and is the precursor to norepinephrine and epinephrine. Dopamine is a major transmitter in the extrapyramidal system of the brain, and important in regulating movement. A family of receptors (receptors, dopamine) mediate its action. [PubChem]

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Animal Toxin
Cardiotonic Agent
Dopamine Agent
Drug
Food Toxin
Human Neurotoxin
Metabolite
Natural Compound
Organic Compound
Sympathomimetic

Chemical Structure

MOL SDF PDB SMILES InChI

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 Mass

153.178 g/mol

Monoisotopic Mass

153.079 g/mol

CAS Registry Number

51-61-6

IUPAC Name

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

Traditional Name

dopamine

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Brain
Epidermis
Fibroblasts
Kidney
Muscle
Myelin
Nerve Cells
Neuron
Pancreas
Placenta
Platelet
Skeletal Muscle
Spleen
Striatum
Testes

Pathways

Name	SMPDB Link	KEGG Link
Catecholamine Biosynthesis	SMP00012	map00350
Tyrosine Metabolism	SMP00006	map00350
Aromatic L-Aminoacid Decarboxylase Deficiency	SMP00170	Not Available
Dopamine beta-hydroxylase deficiency	SMP00498	Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	128°C
Boiling Point	227°C at 2.30E+01 mm Hg
Solubility	600 g/L

Predicted 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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-1900000000-117a1a7207245f5377e7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-00di-1900000000-8b7dcae82868308513da	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-117a1a7207245f5377e7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-1900000000-8b7dcae82868308513da	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-8900000000-752bc8c11fa321b8a7ac	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0089-9280000000-c894c19dda88ac048dd4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0uxu-4900000000-ff51177ebcb89b8c956c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9200000000-a554eb700a06cecb8292	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9000000000-db9813e1025f237a549b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-27e0d71db6d14d79759c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0uk9-0900000000-f1cf97c0d0dd509e229e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-0900000000-aa09a2411e287abe74ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-1900000000-97c42b109cab2005373d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-006x-9700000000-974bd18febffcceea2d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0f79-0900000000-099173d4201beca9e548	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-1900000000-9dc09f2661247c9d84b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9300000000-8b85fa9aac1ffb4c2873	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-9ea16d2057010279d433	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014l-9000000000-32ca2db8fe2b4729ab94	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0f79-0900000000-ff587935c79b4592ffcf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-1900000000-8a35d8a2241bc18d6c50	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9300000000-356a4b8f268863c7893e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-a88c1004f357858fbc6c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014l-9000000000-271874005dcb90288512	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-0900000000-cfa7e1cb9f02ffb4447d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0900000000-4e409c6edda911de39fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-90aa0e0866454c2eacc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9400000000-210fd696305d8cf76164	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-ff95007680e484d3c57e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-6dcfecebbd98220ef746	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kil-6900000000-f476cfd569c441bc84aa	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00e9-8900000000-88acdc978fe4a64e0fc5	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Dopamine is rapidly absorbed from the small intestine.

Mechanism of Toxicity

Dopamine is a precursor to norepinephrine in noradrenergic nerves and is also a neurotransmitter in certain areas of the central nervous system. Dopamine produces positive chronotropic and inotropic effects on the myocardium, resulting in increased heart rate and cardiac contractility. This is accomplished directly by exerting an agonist action on beta-adrenoceptors and indirectly by causing release of norepinephrine from storage sites in sympathetic nerve endings. In the brain, dopamine actas as an agonist to the five dopamine receptor subtypes (D!, D2, D3, D4, D5).

Metabolism

Biotransformation of dopamine proceeds rapidly to yield the principal excretion products, 3-4-dihydroxy-phenylacetic acid (DOPAC) and 3-methoxy-4-hydroxy-phenylacetic acid (homovanillic acid, HVA). Route of Elimination: It has been reported that about 80% of the drug is excreted in the urine within 24 hours, primarily as HVA and its sulfate and glucuronide conjugates and as 3,4-dihydroxyphenylacetic acid. A very small portion is excreted unchanged. Half Life: 2 minutes

Toxicity Values

LD₅₀ oral mice = 1460 mg/kg, LD₅₀ oral rats = 1780 mg/kg

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the correction of hemodynamic imbalances present in the shock syndrome due to myocardial infarction, trauma, endotoxic septicemia, open-heart surgery, renal failure, and chronic cardiac decompensation as in congestive failure

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of dopamine are associated with at least 2 inborn errors of metabolism including: Aromatic L-Amino acid Decarboxylase Deficiency and Norepinephrine deficiency.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00988

HMDB ID

HMDB0000073

FooDB ID

FDB012163

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001408

BiGG ID

42467

BioCyc ID

DOPAMINE

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB00073

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.

MSDS

Link

General References

1. 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.

2. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.

3. 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.

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.

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.

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.

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.

8. Bauman A: Unilateral adrenal catecholamine excess. Pheochromocytoma or possible sporadic medullary hyperplasia. Arch Intern Med. 1982 Feb;142(2):377-8.

9. 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.