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]
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| 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 | |
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| 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
- 3,4-Dihydroxyphenylacetaldehyde (DOPAL)
- 5-Hydroxyindoleacetaldehyde (5-HIAL)

