5-HYDROXYINDOLE-3-ACETIC ACID Chemical Properties

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 Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

NL3650000

F 

8-10-23

HS Code 

29339980

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-HYDROXYINDOLE-3-ACETIC ACID Usage And Synthesis

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.

5-HYDROXYINDOLE-3-ACETIC ACID(54-16-0)Related Product Information

• 5-METHYLINDOLE-3-CARBOXALDEHYDE
• ETHYL 2-METHYL-2,3-DIHYDRO-INDOLE-3-CARBOXYLATE
• 5-Methoxy-3-indolecarboxylic acid
• 1-Methylindole-2-carboxylic acid
• 1-INDOLEPROPIONIC ACID
• 4-Methoxy-1H-indole-2-carboxylic acid
• 1-Methylindole-3-carboxaldehyde
• 3-Indolepropionic acid
• Methyl indole-5-carboxylate
• N-[(tert-Butoxy)carbonyl]-D-tryptophan
• 5-Bromo-6-chloro-3-indolyl-beta-D-galactoside
• Indole-3-acetic acid
• 5-Hydroxyindole
• 5-HYDROXYINDOLE-3-ACETIC ACID
• 5-hydroxyindole-3-acetic acid*dicyclohexylammoniu,5-HYDROXYINDOLE-3-ACETIC ACID*DICYCLOHEX YLAMMONIUM,5-HYDROXYINDOLE-3-ACETIC ACID DICYCLOHEXYLAMMONIUM SALT
• 5-Hydroxyindole-3-acetic acid diethylammonium salt
• 2,3-DIHYDRO-5-HYDROXYINDOLE-3-ACETIC ACID
• 5-Hydroxyindole-3-Acetic Acid-D2