3,4-Dihydroxyphenylacetic acid

3,4-Dihydroxyphenylacetic acid
Identifiers
CAS number 102-32-9 YesY
PubChem 547
ChemSpider 532 YesY
DrugBank DB01702
MeSH 3,4-Dihydroxyphenylacetic+Acid
ChEBI CHEBI:41941 YesY
ChEMBL CHEMBL1284 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H8O4
Molar mass 168.15 g mol−1
 YesY acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

3,4-Dihydroxyphenylacetic acid (DOPAC) is a metabolite of the neurotransmitter dopamine.

Dopamine can be metabolized into one of three substances. One such substance is DOPAC. Another is 3-methoxytyramine (3-MT). Both of these substances are degraded to form homovanillic acid (HVA). Both degradations involve the enzymes monoamine oxidase (MAO) and catechol-O-methyl transferase (COMT), albeit in reverse order: MAO catalyzes dopamine to DOPAC, and COMT catalyzes DOPAC to HVA; whereas COMT catalyzes dopamine to 3-MT and MAO catalyzes 3-MT to HVA. The third metabolic end-product of dopamine is norepinephrine (noradrenaline).

DOPAC can be oxidized by hydrogen peroxide, leading to the formation of toxic metabolites which destroy dopamine storage vesicles in the substantia nigra. This may contribute to the failure of levodopa treatment of Parkinson's disease. A MAO-B inhibitor such as selegiline or rasagiline can prevent this from happening.

Biodegradation of dopamine

References


Wikimedia Foundation. 2010.

Look at other dictionaries:

  • Homogentisic acid — IUPAC name (2,5 Dihydroxyphenyl)acetic acid …   Wikipedia

  • homogentisic acid — noun 2,5 dihydroxyphenylacetic acid. Syn: alcapton, alkapton, melanic acid …   Wiktionary

  • Dopac — chembox new ImageFile=3,4 Dihydroxyphenylacetic acid.svg ImageSize= IUPACName=2 (3,4 dihydroxyphenyl)acetic acid OtherNames= Section1=Chembox Identifiers CASNo=102 32 9 MeSHName=3,4 Dihydroxyphenylacetic+Acid PubChem=547 ChemSpiderID = 532 SMILES …   Wikipedia

  • Metabolic intermediate — Metabolic intermediates refers to molecules which are the precursors or metabolites of biologically significant molecules. Although these intermediates are of relatively minor direct importance to cellular function, they can play important roles… …   Wikipedia

  • Dictionary of natural phenols and polyphenols molecular formulas — Natural polyphenols molecular formulas are generally formed from C, H and O. The entries are sorted by mass. Formula Example Exact mass (u) C8H10O 4 Ethylphenol, others 122.073164 C6H6O3 Hydroxyquinol, others 126.031694 C7H6O3 2 Hydroxybenzoic… …   Wikipedia

  • Monoamine oxidase — MAO redirects here. For other uses, see Mao (disambiguation). Monoamine oxidase Identifiers EC number 1.4.3.4 CAS number …   Wikipedia

  • Tyrosine — NatOrganicBox name=( S ) 2 Amino 3 (4 hydroxyphenyl) propanoic acid PubChem = 1153 CAS = 60 18 4 SMILES = N [C@@H] (Cc1ccc(O)cc1)C(O)=O C=9 | H=11 | N=1 | O=3 mass=181.19 g/molTyrosine (abbreviated as Tyr or Y) [cite web | author=IUPAC IUBMB… …   Wikipedia

  • Dopamine — For other uses, see Dopamine (disambiguation). Dopamine …   Wikipedia

  • Myopia — For other uses, see Myopia (disambiguation). Myopia Classification and external resources ICD 10 H …   Wikipedia

  • Mesocarb — Systematic (IUPAC) name 5 (Phenylcarbamoylimino) 3 (1 phenylpropan 2 yl) 5H 1,2,3 oxadiazol 3 ium 2 ide Clinical data Pregnancy cat …   Wikipedia


Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”

We are using cookies for the best presentation of our site. Continuing to use this site, you agree with this.