5-HYDROXYINDOLE-3-ACETIC ACID Property

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. 

-20°C

solubility 

Soluble in ethanol (50 mg/ml).

pka

4.54±0.30(Predicted)

form 

crystalline

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

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

NL3650000

F 

8-10-23

HS Code 

29339980

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

5-HYDROXYINDOLE-3-ACETIC ACID Chemical Properties,Usage,Production

Description

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.

Chemical Properties

beige crystalline powder

Uses

5-Hydroxyindole-3-acetic acid is a major serotonin metabolite.

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.

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.