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CAS 54-16-0

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5-Hydroxyindoleacetic acid

Description:
5-Hydroxyindoleacetic acid (5-HIAA) is a metabolite of serotonin, primarily found in the human body and other organisms. It is characterized by its chemical structure, which includes an indole ring and a carboxylic acid group, contributing to its biological activity. 5-HIAA is soluble in water and exhibits a weakly acidic nature, with a pKa that allows it to exist predominantly in its anionic form at physiological pH. This compound is significant in clinical biochemistry, as its levels in urine can be indicative of serotonin metabolism and are often measured in the diagnosis of certain neuroendocrine tumors, such as carcinoid tumors. Additionally, 5-HIAA has been studied for its potential role in various neurological conditions and its relationship with mood disorders. Its stability under standard laboratory conditions makes it a useful biomarker in research and clinical settings. Overall, 5-HIAA serves as an important compound in understanding serotonin dynamics and its implications in health and disease.
Formula:C10H9NO3
InChI:InChI=1/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)/p-1
InChI key:InChIKey=DUUGKQCEGZLZNO-UHFFFAOYSA-N
SMILES:C(C(O)=O)C=1C=2C(NC1)=CC=C(O)C2
Synonyms:
  • (5-Hydroxy-1H-indol-3-yl)acetic acid
  • (5-hydroxy-1H-indol-3-yl)acetate
  • 1H-Indole-3-acetic acid, 5-hydroxy-
  • 2-(5-Hydroxy-1H-indol-3-yl)acetic acid
  • 5-Hiaa
  • 5-Hydroxy-1H-indole-3-acetic acid
  • 5-Hydroxy-3-indolylacetate
  • 5-Hydroxy-IAA
  • 5-Hydroxyheteroauxin
  • 5-Hydroxyindol-3-Ylacetic Acid
  • See more synonyms
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