5-Hydroxyindol-3-ylessigsure

Bezeichnung:5-Hydroxyindol-3-ylessigsure

CAS-Nr54-16-0

Englisch Name:5-Hydroxyindole-3-acetic acid

CBNumberCB0362913

SummenformelC10H9NO3

Molgewicht191.18

MOL-Datei54-16-0.mol

Synonyma

5-Hydroxyindol-3-ylessigsure

5-Hydroxyindol-3-ylessigsure physikalisch-chemischer Eigenschaften

Schmelzpunkt	161-164 °C (dec.) (lit.)
Siedepunkt	326.92°C (rough estimate)
Dichte	1.2722 (rough estimate)
Brechungsindex	1.5310 (estimate)
storage temp.	-20°C
Löslichkeit	Soluble in ethanol (50 mg/ml).
pka	4.54±0.30(Predicted)
Aggregatzustand	crystalline
Farbe	off-white to purple
Sensitive	Light Sensitive
BRN	168797
Stabilität	Air Sensitive, Light Sensitive
Major Application	clinical testing
InChI	1S/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)
InChIKey	DUUGKQCEGZLZNO-UHFFFAOYSA-N
SMILES	OC(=O)Cc1c[nH]c2ccc(O)cc12
CAS Datenbank	54-16-0

Sicherheit

S-Sätze:	22-24/25
WGK Germany	3
RTECS-Nr.	NL3650000
F	8-10-23
HS Code	29339980
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

5-Hydroxyindole-3-acetic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
5-hydroxy Indole-3-acetic acid (5-HIAA) is the primary metabolite of serotonin (5-HT; ). It is formed when 5-HT is metabolized by monamine oxidase and aldehyde dehydrogenase in the liver. 5-HIAA is excreted in urine and has been used as a biomarker for detection of neuroendocrine tumors and an internal standard for the quantification of serotonin metabolism in rat brain using mass spectrometry. 5-HIAA has also been associated with autism, insomnia, and chronic migraine.
Chemische Eigenschaften
beige crystalline powder
Verwenden
5-Hydroxyindole-3-acetic acid is a major serotonin metabolite.
Verwenden
5-Hydroxyindole-3-acetic acid is an impurity of chlorpheniramine (C424300), an antihistaminic agent.
Definition
ChEBI: A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.
Allgemeine Beschreibung
5-Hydroxyindole-3-acetic acid (5-HIAA) is the catabolic end product of serotonin pathway. 5-HIAA is present in body fluids like cerebrospinal fluid (CSF), blood and urine. The expression levels of 5-HIAA is different among the normal and cancer patients. Sepiapterin reductase deficiency results in low level of 5-HIAA in CSF. 5-HIAA level is low in CSF in patients with bipolar 1 disorder with childhood attention-deficit hyperactivity disorder (ADHD).
Mechanism of action
The primary product of the metabolism of serotonin. Formed by the oxidative deamination of serotonin by monoamine oxidase, presumably the A isozyme, 5-HIAA is subsequently cleared by an active transport mechanism. Unlike serotonin, 5-HIAA is not a neurotransmitter and thus its formation contributes to the termination of the synaptic actions of serotonin. Inhibition of monoamine oxidase activity enhances and prolongs the actions of serotonin.
Einzelnachweise
[1] JEAN-BENOT CORCUFF. Urinary sampling for 5HIAA and metanephrines determination: revisiting the recommendations.[J]. Endocrine Connections, 2017, 6 6: R87-R98. DOI: 10.1530/ec-17-0071
[2] YANNICK VERMEIREN . Monoaminergic neurotransmitter alterations in postmortem brain regions of depressed and aggressive patients with Alzheimer’s disease[J]. Neurobiology of Aging, 2014, 35 12: Pages 2691-2700. DOI: 10.1016/j.neurobiolaging.2014.05.031

5-Hydroxyindol-3-ylessigsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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