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3,4-Dihydroxyphenylglycolaldehyde

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Neurotransmitter metabolite and neurotoxin

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 theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL), also known as3,4-dihydroxymandelaldehyde (DHMAL) as well asnorepinephrine aldehyde orepinephrine aldehyde, is ametabolite of themonoamine neurotransmitters norepinephrine andepinephrine. DOPEGAL is anoradrenergic neurotoxin.^[1]

Formation

[edit]

DOPEGAL is formed bymonoamine oxidase (MAO) viaoxidative deamination.^[3]^[4]^[5]^[6]^[7]^[8] Following its formation, DOPEGAL ismetabolized. Through the metabolism process, it is converted into3,4-dihydroxymandelic acid (DHMA) viaaldehyde dehydrogenase (ALDH), or into3,4-dihydroxyphenylglycol (DHPG) viaaldehyde reductase (ALR).^[2]^[4]^[5]^[6]^[7]

References

[edit]

^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 ^bFigure 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. Retrieved8 September 2024.
^^a ^bGoldstein 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 ^bTipton 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 ^bBortolato 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 ^bKawamura 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.

Neurotransmitter metabolic intermediates

Catecholamines

Anabolism

Phenylalanine →Tyrosine →DOPA (levodopa) →Dopamine →Norepinephrine →Epinephrine

Catabolism

Dopamine	3,4-Dihydroxyphenylacetaldehyde (DOPAL) 3,4-Dihydroxyphenylacetic acid (DOPAC) Homovanillyl alcohol Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET) 3-Methoxytyramine (3-MT) Homovanillic acid (HVA)
Norepinephrine	3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL) 3,4-Dihydroxymandelic acid (DHMA) Normetanephrine 3-Methoxy-4-hydroxymandelaldehyde (MHMAL) Vanillylmandelic acid (VMA) 3,4-Dihydroxyphenylethylene glycol (DOPEG, DHPG) 3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG)
Epinephrine	3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL) Metanephrine 3-Methoxy-4-hydroxymandelaldehyde (MHMAL)

Tryptophan→Serotonin

Anabolism	Tryptophan 5-Hydroxytryptophan (5-HTP)
Catabolism	5-Hydroxyindoleacetaldehyde (5-HIAL) 5-Hydroxyindoleacetic acid (5-HIAA) 5-Hydroxytryptophol (5-HTOL)

v t e Monoaminergic neurotoxins
Dopaminergic	2′-CH₃-MPTP (2′-methyl-MPTP) 2,4,5-THA 2,4,5-THMA 4-MMA 5-S-Cysteinyldopamine 5,6-DHT 6-Hydroxydopa 6-OHDA quinone 6,7-DHT ALDH inhibitors (e.g.,disulfiram,methylmercury) Amphetamine Benomyl Daidzin Dieldrin DOPA quinone DOPAL DOPAL quinone Dopamine Dopamine quinone Fenpropathrin Haloperidol HPP⁺ HPTP Mancozeb Maneb Mephedrone Methamphetamine Methcathinone Methylone MPP⁺ (cyperquat) MPTP N-Methylnorsalsolinol Norsalsolinol Oxidopamine (6-OHDA) Paraquat Rotenone Salsolinol Ziram
Noradrenergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4,5-THA 4,5-DHT 5,6-DHT 5,7-DHT 6-Hydroxydopa DOPEGAL DSP-4 MDA (tenamfetamine) Oxidopamine (6-OHDA) Xylamine
Serotonergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4-DCA 2,4,5-THA 2,4,5-THMA 3-CA 3,4-DCA 4-CAB (α-ethyl-PCA) 4-CMA 4-HO-5-MeO-T 4,5-DHT 5-IAI 5-MAPB 5-MeO-DiPT 5,6-DHT 5,7-DHT 6,7-DHT αET ETAI Fenfluramine Haloperidol HHA (α-methyldopamine) HHMA (α-methylepinine, α,N-dimethyldopamine) HPP⁺ HPTP MBDB MDA (tenamfetamine) MDMA (midomafetamine) Mephedrone Methamphetamine Methylone Norfenfluramine PBA PBMA PCA PCMA PIA TAI
Unsorted	5-HIAL RHPP⁺ RHPTP
See also:Receptor/signaling modulators •Adrenergics •Dopaminergics •Melatonergics •Serotonergics •Monoamine reuptake inhibitors •Monoamine releasing agents •Monoamine metabolism modulators

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