ChemicalBook CAS DataBase List 54-16-0

54-16-0

Name	5-HYDROXYINDOLE-3-ACETIC ACID
CAS	54-16-0
EINECS(EC#)	200-195-4
Molecular Formula	C10H9NO3
MDL Number	MFCD00005639
Molecular Weight	191.18
MOL File	54-16-0.mol

Chemical Properties

Appearance	beige crystalline powder
Melting point	161-164 °C (dec.)(lit.)
Boiling point	326.92°C (rough estimate)
density	1.2722 (rough estimate)
refractive index	1.5310 (estimate)
storage temp.	2-8°C
solubility	Soluble in ethanol (50 mg/ml).
form	crystalline
pka	4.54±0.30(Predicted)
color	off-white to purple
Sensitive	Light Sensitive
BRN	168797
Stability:	Air Sensitive, Light Sensitive
InChIKey	DUUGKQCEGZLZNO-UHFFFAOYSA-N
CAS DataBase Reference	54-16-0

Safety Data

Safety Statements	22-24/25 less more
WGK Germany	3
RTECS	NL3650000
F	8-10-23
HS Code	29339980

Hazard Information

Chemical Properties

beige crystalline powder

Uses

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.

Description

5-hydroxy Indole-3-acetic acid (5-HIAA) is the primary metabolite of serotonin (5-HT; Item No. 14332). 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.

General Description

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.

storage

Store at 2-8°C

References

[1] JEAN-BENO?T 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

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