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.
For research use only. We do not sell to patients.
- CAS No.: 1892-21-3
- Formula: C10H9NO2
- Molecular Weight:175.18
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
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Biological Activity
Description
In Vitro
5-Hydroxyindoleacetaldehyde (100 µM; 60 min) oligomerizes human recombinant alpha-synuclein to more than 10-fold that of the control in vitro, whereas Pargyline (HY-A0091A) blocks this effect[7].
5-Hydroxyindoleacetaldehyde (generated intracellularly from 500 µM 5-Hydroxytryptophan (5-HTP) (HY-N0122); 6 h) increases alpha-synuclein dimers in PC12 cells overexpressing alpha-synuclein, whereas Pargyline (10 µM) attenuates this effect[7].
5-Hydroxyindoleacetaldehyde (50 μM NADPH (HY-113324)) is preferentially oxidized by aldehyde dehydrogenase in porcine caudate nucleus cytosol at low substrate concentrations (Km 0.2 μM; Vmax 0.6 nmol/min × mg protein), and as aldehyde concentration increases, the low-Km aldehyde reductase (Km 5.9 μM; Vmax 1.0 nmol/min × mg protein) becomes more important[3].
5-Hydroxyindoleacetaldehyde (0.5-4.0 ×10-6 M; preincubation for 10 min, incubation for 30 min) binds to rat brain homogenates in a concentration-dependent manner, and this incorporation is reduced by 5-hydroxyindole (HY-W001160) and catechol, but not by indole, 5-methoxyindole (HY-W007328), 5-methoxy-3-indolecarboxaldehyde, or Acetaldehyde[4].
5-Hydroxyindoleacetaldehyde (2.8-11.4 × 10-6 M; 12 min at 37°C) is oxidized by rat brain mitochondrial aldehyde dehydrogenase with a Km of 5.44 × 10-6 M, and this oxidation is competitively inhibited by Acetaldehyde[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 1892-21-3
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Molecular Weight 175.18
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Formula C10H9NO2
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SMILES
O=CCC1=CNC2=C1C=C(O)C=C2
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Synonyms
5-HIAAld; 5-HIAL; 5-OH-IAAld
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
5-Hydroxyindoleacetaldehyde Related Classifications
HY-160936 Related Classifications
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Keywords
- 5-Hydroxyindoleacetaldehyde
- 1892-21-3
- 5-HIAAld
- 5-HIAL
- 5-OH-IAAld
- α-synuclein
- Drug Metabolite
- α-Syn
- CHO cells
- Parkinson's disease
- aldehyde dehydrogenase
- aldehyde reductase
- hydroxyindoleacetic acid
- monoamine oxidase-A
- sedation
- serotonin catabolism
- tryptophan metabolite
- α-synuclein oligomerization
- Inhibitor
- inhibitor
- inhibit