5-hydroxyindolylacetic acid

Structural formula
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
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
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	1125 mg kg −1 ( LD 50 , mouse , ip )
	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

↑ ^a ^b ^c ^d data sheet 5-Hydroxyindole-3-acetic acid from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).
↑ 5-HIAA: The Test | 5-hydroxyindoleacetic acid. May 22, 2016, accessed March 27, 2019 .
↑ 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).
↑ Thomas Bronisch: The suicide: causes warning signals prevention. 5th edition, CH Beck, Munich 2007, ISBN 978-3-406-55967-9 , pp. 63-65.
↑ 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.

[sigma-1] ta 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 .

[Bentele-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.