Chemistry:3,4-Dihydroxyphenylglycolaldehyde

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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]

See also

References

  1. ↑ "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. June 2007. doi:10.1124/pr.59.2.1. PMID 17379813. 
  2. ↑ 2.0 2.1 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. ↑ "3,4-Dihydroxymandelaldehyde". https://pubchem.ncbi.nlm.nih.gov/compound/151725. 
  4. ↑ 4.0 4.1 "The catecholaldehyde hypothesis: where MAO fits in". J Neural Transm (Vienna) 127 (2): 169–177. February 2020. doi:10.1007/s00702-019-02106-9. PMID 31807952. 
  5. ↑ 5.0 5.1 "90 years of monoamine oxidase: some progress and some confusion". J Neural Transm (Vienna) 125 (11): 1519–1551. November 2018. doi:10.1007/s00702-018-1881-5. PMID 29637260. 
  6. ↑ 6.0 6.1 "Behavioral outcomes of monoamine oxidase deficiency: preclinical and clinical evidence". Int Rev Neurobiol. International Review of Neurobiology 100: 13–42. 2011. doi:10.1016/B978-0-12-386467-3.00002-9. ISBN 978-0-12-386467-3. PMID 21971001. 
  7. ↑ 7.0 7.1 "Aldose reductase, a key enzyme in the oxidative deamination of norepinephrine in rats". Biochem Pharmacol 58 (3): 517–524. August 1999. doi:10.1016/s0006-2952(99)00121-5. PMID 10424772. 
  8. ↑ "Aldose reductase: an aldehyde scavenging enzyme in the intraneuronal metabolism of norepinephrine in human sympathetic ganglia". Auton Neurosci 96 (2): 131–139. March 2002. doi:10.1016/s1566-0702(01)00385-x. PMID 11958479. 

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