1892-21-3
Chemical Structure
5-Hydroxyindoleacetaldehyde
Synonym(s): 5-HIAAld; 5-HIAL; 5-OH-IAAld
- No. CAS: 1892-21-3
- Formula:C10H9NO2
- Molecular Weight:175.18
InChIKey: OBFAPCIUSYHFIE-UHFFFAOYSA-N
SMILES: O=CCC1=CNC2=C1C=C(O)C=C2
Biological Activity: 5-Hydroxyindoleacetaldehyde (5-HIAAld; 5-HIAL; 5-OH-IAAld) is a tryptophan metabolite and an intermediate in the catabolism of serotonin (HY-B1473A), produced from serotonin by monoamine oxidase-A and mainly oxidized to hydroxyindoleacetic acid by aldehyde dehydrogenase (ALDH) (HY-P2947); when 5-Hydroxyindoleacetaldehyde accumulates, it promotes α-synuclein (α-synuclein) oligomerization and exhibits cytotoxicity, and it also binds to acid-insoluble macromolecular fractions in brain homogenates, alters cortical potentials, and induces sedation/sleep. 5-Hydroxyindoleacetaldehyde can be used in research on Parkinson's disease[1][2][3][4][5][6][7][8].
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5-Hydroxyindoleacetaldehyde | 5-Hydroxyindoleacetaldehyde (5-HIAAld; 5-HIAL; 5-OH-IAAld) is a tryptophan metabolite and an intermediate in the catabolism of serotonin (HY-B1473A), produced from serotonin by monoamine oxidase-A and mainly oxidized to hydroxyindoleacetic acid by aldehyde dehydrogenase (ALDH) (HY-P2947); when 5-Hydroxyindoleacetaldehyde accumulates, it promotes α-synuclein (α-synuclein) oligomerization and exhibits cytotoxicity, and it also binds to acid-insoluble macromolecular fractions in brain homogenates, alters cortical potentials, and induces sedation/sleep. 5-Hydroxyindoleacetaldehyde can be used in research on Parkinson's disease. | |||||||||||||||||||||
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References
- [1]. Alden N, et al. Using Metabolomics to Identify Cell Line-Independent Indicators of Growth Inhibition for Chinese Hamster Ovary Cell-based Bioprocesses. Metabolites. 2020 May 15;10(5):199.
- [2]. Minegishi A, et al. Modulation of seizure pattern in the rat by neutral metabolites of indoleamines. Journal of Pharmacy and Pharmacology. 1981 Sep;33(1):395-7.
- [3]. Duncan RJ, et al. SOME ENZYMIC ASPECTS OF THE PRODUCTION OF OXIDIZED OR REDUCED METABOLITES OF CATECHOLAMINES AND 5‐HYDROXYTRYPTAMINE BY BRAIN TISSUES. Journal of Neurochemistry. 1974 May;22(5):663-9.
- [4]. Ungar F, et al. Inhibition of binding of aldehydes of biogenic amines in tissues. Biochemical pharmacology. 1973 Aug 1;22(15):1905-13.
- [5]. Lahti RA, et al. Acetaldehyde—an inhibitor of the enzymatic oxidation of 5-hydroxyindoleacetaldehyde. Biochemical Pharmacology. 1969 Feb 1;18(2):535-8.
- [6]. Cagle BS, et al. Biogenic Aldehyde-Mediated Mechanisms of Toxicity in Neurodegenerative Disease. Current opinion in toxicology. 2019 Feb;13:16-21.
- [7]. Jinsmaa Y, et al. The serotonin aldehyde, 5-HIAL, oligomerizes alpha-synuclein. Neuroscience letters. 2015 Mar 17;590:134-7.
- [8]. Warbritton JD, et al. Increased sensitivity to intracerebroventricular infusion of serotonin and deaminated indoles after lesioning rat with dihydroxytryptamine. Brain research. 1980 Feb 10;183(2):355-66.
