5-hydroxyindolylacetic acid

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Structural formula
Structural formula of 5-hydroxyindolylacetic acid
General
Surname 5-hydroxyindolylacetic acid
other names
  • 5-hydroxyindole acetic acid
  • 5-HIAA
  • 2- (5-Hydroxy-1 H -indol-3-yl) acetic acid ( IUPAC )
Molecular formula C 10 H 9 NO 3
Brief description

light red to purple powder

External identifiers / databases
CAS number 54-16-0
EC number 200-195-4
ECHA InfoCard 100,000.179
PubChem 1826
ChemSpider 1760
Wikidata Q238532
properties
Molar mass 191.18 g mol −1
Physical state

firmly

Melting point

161–164 ° C (decomposition)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

1125 mg kg −1 ( LD 50mouseip )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

5-hydroxyindoleacetic acid (5-HIAA, engl .: 5-hydroxyindoleacetic acid = 5-HIAA) is a metabolite ( metabolite ) of serotonin , and can be used to determine the serotonin levels.

use

In laboratory medicine , 5-HIES is used to detect a carcinoid in enterochromaffin cells . For this purpose, it is from the urine by diethyl ether extracted , and then the solvent evaporated. With 1-nitroso-2-naphthol, a red dye is formed whose color strength increases with the concentration of 5-HIES.

Sensitive detection of 5-HIES in addition to other neurotransmitters such as dopamine , serotonin and noradrenaline , for example in microdialysates, is possible using liquid chromatography ( HPLC ) coupled with amperometric detection .

Biological importance

A still unexplained associated low levels of 5-HIAA in the are cerebrospinal fluid ( CSF ) of a "hard" in people with the frequency of occurrence suicide attempt in depressive linked patients and in children with violent behavior. In monkeys, too, there was a connection between low 5-HIES levels in the CSF and increased aggressiveness .

literature

  • Hans D. Bruhn, Ulrich R. Fölsch: Laboratory medicine: indications, methodology and laboratory values. Pathophysiology and Clinic . Schattauer, Stuttgart 2008, ISBN 978-3-7945-2550-8 , pp. 381 ( limited preview in Google Book Search [accessed July 2, 2010]).
  • Eckhart Buddecke, Michael MJ Fischer: Pathophysiology. Pathobiochemistry. Clinical Chemistry. For medical students and doctors. Gruyter, ISBN 978-3-11-012844-4 , pp. 194 ( limited preview in Google Book Search [accessed July 2, 2010]).

Individual evidence

  1. a b c d data sheet 5-Hydroxyindole-3-acetic acid from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).
  2. 5-HIAA: The Test | 5-hydroxyindoleacetic acid. May 22, 2016, accessed March 27, 2019 .
  3. C. Bentele: Establishment of a method for high-performance liquid chromatography (HPLC) with electrochemical detection (ECD) for the simultaneous measurement of 3-methoxy-4-hydroxyphenol glycol, 5-hydroxyindole acetic acid and homovanillic acid in the liquor of patients with fibromyalgia syndrome and neurological diseases. Dissertation, Ludwig Maximilians University Munich 2004 PDF (accessed on August 26, 2012).
  4. Thomas Bronisch: The suicide: causes warning signals prevention. 5th edition, CH Beck, Munich 2007, ISBN 978-3-406-55967-9 , pp. 63-65.
  5. Helmut Remschmidt , Reinhard Walter, Jürgen Schörnberger: Child delinquency: Violations of the law by persons under criminal law and their consequences. Springer, 2009, ISBN 978-3-642-01136-8 , p. 37.