3,4-Dihydroxyphenylglycolaldehyde

Neurotransmitter metabolite and neurotoxin From Wikipedia, the free encyclopedia

3,4-Dihydroxyphenylglycolaldehyde (also known as DOPEGAL, 3,4-dihydroxymandelaldehyde, DHMAL, norepinephrine aldehyde, or epinephrine aldehyde) is a metabolite of the monoamine neurotransmitters norepinephrine and epinephrine. DOPEGAL is a noradrenergic neurotoxin.[1]

Quick facts Names, Identifiers ...
3,4-Dihydroxyphenylglycolaldehyde
Names
Preferred IUPAC name
(3,4-Dihydroxyphenyl)(hydroxy)acetaldehyde
Other names
DHMAL; 3,4-Dihydroxyphenylglycolaldehyde; 3,4-Dihydroxyphenylglycol aldehyde; DOPEGAL; DOPGAL; DHPGALD; Norepinephrine aldehyde; Epinephrine aldehyde; Noradrenaline aldehyde; Adrenaline aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C8H8O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-4,8,10-12H
    Key: YUGMCLJIWGEKCK-UHFFFAOYSA-N
  • C1=CC(=C(C=C1C(C=O)O)O)O
Properties
C8H8O4
Molar mass 168.148 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Formation

DOPEGAL is formed by monoamine oxidase (MAO) via oxidative deamination.[2][3][4][5][6][7] Following its formation, DOPEGAL is metabolized. Through the metabolism process, it is converted into 3,4-dihydroxymandelic acid (DHMA) via aldehyde dehydrogenase (ALDH), or into 3,4-dihydroxyphenylglycol (DHPG) via aldehyde reductase (ALR).[8][3][4][5][6]

Formation of DOPEGAL (norepinephrine aldehyde) from norepinephrine.[8]

See also

References

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