3,4-Dihydroxyphenylglycolaldehyde

3,4-Dihydroxyphenylglycolaldehyde
Names
	IUPAC name 2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde
	Other names DHMAL; 3,4-Dihydroxyphenylglycolaldehyde; 3,4-Dihydroxyphenylglycol aldehyde; DOPEGAL; DOPGAL; DHPGALD; Norepinephrine aldehyde; Epinephrine aldehyde; Noradrenaline aldehyde; Adrenaline aldehyde
Identifiers
CAS Number	13023-73-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27852;
ChemSpider	133725;
KEGG	C05577;
PubChem CID	151725;
CompTox Dashboard (EPA)	DTXSID30897223 ;
	InChI 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;
	SMILES C1=CC(=C(C=C1C(C=O)O)O)O;
Properties
Chemical formula	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). Infobox references

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

Formation

Formation of DOPEGAL (norepinephrine aldehyde) from norepinephrine.^[2]

DOPEGAL is formed by monoamine oxidase (MAO) via oxidative deamination.^[3]^[4]^[5]^[6]^[7]^[8] 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).^[2]^[4]^[5]^[6]^[7]

References

^ Marchitti SA, Deitrich RA, Vasiliou V (June 2007). "Neurotoxicity and metabolism of the catecholamine-derived 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde: the role of aldehyde dehydrogenase". Pharmacol Rev. 59 (2): 125–150. doi:10.1124/pr.59.2.1. PMID 17379813.
^ ^a ^b Figure 11-4 in: Flower, R.; Rang, H. P.; Dale, M. M.; Ritter, J. M. (2007). Rang & Dale's Pharmacology. Edinburgh: Churchill Livingstone. ISBN 978-0-443-06911-6.
^ "3,4-Dihydroxymandelaldehyde". PubChem. Retrieved 8 September 2024.
^ ^a ^b Goldstein DS (February 2020). "The catecholaldehyde hypothesis: where MAO fits in". J Neural Transm (Vienna). 127 (2): 169–177. doi:10.1007/s00702-019-02106-9. PMC 10680281. PMID 31807952.
^ ^a ^b Tipton KF (November 2018). "90 years of monoamine oxidase: some progress and some confusion". J Neural Transm (Vienna). 125 (11): 1519–1551. doi:10.1007/s00702-018-1881-5. PMID 29637260.
^ ^a ^b Bortolato M, Shih JC (2011). "Behavioral outcomes of monoamine oxidase deficiency: preclinical and clinical evidence". Int Rev Neurobiol. International Review of Neurobiology. 100: 13–42. doi:10.1016/B978-0-12-386467-3.00002-9. ISBN 978-0-12-386467-3. PMC 3371272. PMID 21971001.
^ ^a ^b Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Tsai JY, Fujisawa S, Lizak MJ, Sinz A, Sato S (August 1999). "Aldose reductase, a key enzyme in the oxidative deamination of norepinephrine in rats". Biochem Pharmacol. 58 (3): 517–524. doi:10.1016/s0006-2952(99)00121-5. PMID 10424772.
^ Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Fujisawa S, Sato S (March 2002). "Aldose reductase: an aldehyde scavenging enzyme in the intraneuronal metabolism of norepinephrine in human sympathetic ganglia". Auton Neurosci. 96 (2): 131–139. doi:10.1016/s1566-0702(01)00385-x. PMID 11958479.

[MarchittiDeitrichVasiliou2007-1] Marchitti SA, Deitrich RA, Vasiliou V (June 2007). "Neurotoxicity and metabolism of the catecholamine-derived 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde: the role of aldehyde dehydrogenase". Pharmacol Rev. 59 (2): 125–150. doi:10.1124/pr.59.2.1. PMID 17379813.

[Rang&Dale6th-11-4-2] Figure 11-4 in: Flower, R.; Rang, H. P.; Dale, M. M.; Ritter, J. M. (2007). Rang & Dale's Pharmacology. Edinburgh: Churchill Livingstone. ISBN 978-0-443-06911-6.

[PubChem-3] "3,4-Dihydroxymandelaldehyde". PubChem. Retrieved 8 September 2024.

[Goldstein2020-4] Goldstein DS (February 2020). "The catecholaldehyde hypothesis: where MAO fits in". J Neural Transm (Vienna). 127 (2): 169–177. doi:10.1007/s00702-019-02106-9. PMC 10680281. PMID 31807952.

[Tipton2018-5] Tipton KF (November 2018). "90 years of monoamine oxidase: some progress and some confusion". J Neural Transm (Vienna). 125 (11): 1519–1551. doi:10.1007/s00702-018-1881-5. PMID 29637260.

[BortolatoShih2011-6] Bortolato M, Shih JC (2011). "Behavioral outcomes of monoamine oxidase deficiency: preclinical and clinical evidence". Int Rev Neurobiol. International Review of Neurobiology. 100: 13–42. doi:10.1016/B978-0-12-386467-3.00002-9. ISBN 978-0-12-386467-3. PMC 3371272. PMID 21971001.

[KawamuraEisenhoferKopin1999-7] Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Tsai JY, Fujisawa S, Lizak MJ, Sinz A, Sato S (August 1999). "Aldose reductase, a key enzyme in the oxidative deamination of norepinephrine in rats". Biochem Pharmacol. 58 (3): 517–524. doi:10.1016/s0006-2952(99)00121-5. PMID 10424772.

[KawamuraEisenhoferKopin2002-8] Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Fujisawa S, Sato S (March 2002). "Aldose reductase: an aldehyde scavenging enzyme in the intraneuronal metabolism of norepinephrine in human sympathetic ganglia". Auton Neurosci. 96 (2): 131–139. doi:10.1016/s1566-0702(01)00385-x. PMID 11958479.

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3,4-Dihydroxyphenylglycolaldehyde

Formation

See also

References