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dopamine

File:Dopamine.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ170304· pop 87· linked from 4,368 articles

dopamine

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Also known as 3-hydroxytyramine, 4-(2-aminoethyl)catechol, 4-(2-aminoethyl)pyrocatechol, Hydroxytyramin, 4-(2-Aminoethyl)-1,2-benzenediol, 4-(2-azanylethyl)benzene-1,2-diol, Dopastat, alpha-(3,4-Dihydroxyphenyl)-beta-aminoethane

Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized by removing a carboxyl group from a molecule of its precursor chemical, L-DOPA, which is synthesized in the brain and kidneys. Dopamine is also synthesized in plants and most animals. In the brain, dopamine functions as a neurotransmitter—a chemical released by neurons (nerve cells) to send signals to other nerve cells. The brain includes several distinct dopa

OverviewAI-generated

Dopamine is a chemical compound with the formula C₈H₁₁NO₂ and a mass of 153.079. Its IUPAC name is 4-(2-aminoethyl)benzene-1,2-diol. The substance has a melting point of 128 and a defined daily dose of 0.5. It is stylized as "DOPamine" in some contexts.

The compound has a charge of 0 and an xlogP value of -1. It features 66.5 tpsa, with 3 hydrogen bond donors and 3 hydrogen bond acceptors. Its canonical SMILES is C1=CC(=C(C=C1CCN)O)O, and its InChIKey is VYFYYTLLBUKUHU-UHFFFAOYSA-N.

Literature regarding dopamine is extensive. A PubMed query for the term returns 193,546 results. Additionally, the subject is referenced by 4,368 other encyclopedia articles.

Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.IUPAC_name
4-(2-Aminoethyl)benzene-1,2-diol
Drug.image
Dopamine.svg
Drug.image_class
skin-invert-image
Drug.alt
Dopamine structure
Drug.caption
Skeletal formula of dopamine
Drug.image2
Dopamine-based-on-xtal-3D-bs-17.png
Drug.image_class2
bg-transparent
Drug.caption2
Ball-and-stick model of the dopamine molecule as found in solution. In the solid state, dopamine adopts a zwitterionic form.
Drug.source_tissues
Substantia nigra; ventral tegmental area; many others
Drug.target_tissues
System-wide
Drug.receptors
D1, D2, D3, D4, D5, TAAR1
Drug.agonists
Direct: apomorphine, bromocriptineIndirect: cocaine, amphetamine, methylphenidate
Drug.antagonists
Neuroleptics, metoclopramide, domperidone
Drug.precursor
Phenylalanine, tyrosine, and L-DOPA
Drug.biosynthesis
DOPA decarboxylase
Drug.metabolism
MAO, COMT
Drug.CAS_number
51-61-6
Drug.CAS_supplemental
(hydrochloride)

via Wikipedia infobox

Chemical data

Formula
C8H11NO2
Molecular weight
153.18 g/mol
IUPAC name
4-(2-aminoethyl)benzene-1,2-diol
SMILES
C1=CC(=C(C=C1CCN)O)O
InChIKey
VYFYYTLLBUKUHU-UHFFFAOYSA-N
XLogP
-1
Polar surface area
66.5 Ų
H-bond donors
3
H-bond acceptors
3
Formal charge
0

via PubChem

Research

193,546 papers

via PubMed

Wikidata facts

Has part
oxygen
Mass
153.079
Manufacturer
Pfizer
Said to be same as
Dopamine
Has use
medication
Show 14 more facts
Commons category
Dopamine
medical condition treated
neurogenic shock
chemical formula
C₈H₁₁NO₂
topic's main category
Category:Dopamine
canonical SMILES
C1=CC(=C(C=C1CCN)O)O
melting point
128
subject has role
neurotransmitter
found in taxon
Thalictrum flavum
defined daily dose
0.5
contributing factor of
decision making
produced by
Dopaminergic cell groups
different from
Dopamine
stylized name
DOPamine
significant drug interaction
phenelzine
Sources (12)

via Wikidata · CC0

~58 min read

Encyclopedic overview

36 sections
Contents
  • Structure
  • Biochemistry
  • Synthesis
  • Degradation
  • Functions
  • Cellular effects
  • Storage, release, and reuptake
  • {{Anchor|Functions in the brain}} Central nervous system
  • Basal ganglia
  • Reward
  • Pleasure
  • Outside the central nervous system
  • Immune system
  • Kidneys
  • Pancreas
  • Medical uses
  • Disease, disorders, and pharmacology
  • Aging brain
  • Multiple sclerosis
  • Parkinson's disease
  • Drug addiction and psychostimulants
  • Psychosis and antipsychotic drugs
  • Attention deficit hyperactivity disorder
  • Pain
  • Nausea
  • Comparative biology and evolution
  • Microorganisms
  • Animals
  • Plants
  • As a precursor for melanin
  • History and development
  • Polydopamine
  • See also
  • References
  • Further reading
  • External links

Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized by removing a carboxyl group from a molecule of its precursor chemical, L-DOPA, which is synthesized in the brain and kidneys. Dopamine is also synthesized in plants and most animals. In the brain, dopamine functions as a neurotransmitter—a chemical released by neurons (nerve cells) to send signals to other nerve cells. The brain includes several distinct dopamine pathways, one of which plays a major role in the motivational component of reward-motivated behavior. The anticipation of most types of rewards increases the level of dopamine in the brain, and many addictive drugs increase dopamine release or block its reuptake into neurons following release. Other brain dopamine pathways are involved in motor control and in controlling the release of various hormones. These pathways and cell groups form a dopamine system which is neuromodulatory.

In popular culture and media, dopamine is often portrayed as the main chemical of pleasure, but the current opinion in pharmacology is that dopamine instead confers motivational salience; in other words, dopamine signals the perceived motivational prominence (i.e., the desirability or aversiveness) of an outcome, which in turn propels the organism's behavior toward or away from achieving that outcome.

Excerpted from Wikipedia’s “dopamine” article, available under the CC BY-SA 4.0 licence.

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