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HomeProduct name list5-HYDROXYINDOLE-3-ACETIC ACID

5-HYDROXYINDOLE-3-ACETIC ACID

  • CAS NO.:54-16-0
  • Empirical Formula: C10H9NO3
  • Molecular Weight: 191.18
  • MDL number: MFCD00005639
  • EINECS: 200-195-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-29 18:21:28
5-HYDROXYINDOLE-3-ACETIC ACID Structural

What is 5-HYDROXYINDOLE-3-ACETIC ACID?

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

The Uses of 5-HYDROXYINDOLE-3-ACETIC ACID

5-Hydroxyindole-3-acetic acid is an impurity of chlorpheniramine (C424300), an antihistaminic agent.

The Uses of 5-HYDROXYINDOLE-3-ACETIC ACID

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

What are the applications of Application

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

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.

Properties of 5-HYDROXYINDOLE-3-ACETIC ACID

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
CAS DataBase Reference 54-16-0

Safety information for 5-HYDROXYINDOLE-3-ACETIC ACID

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for 5-HYDROXYINDOLE-3-ACETIC ACID

InChIKey DUUGKQCEGZLZNO-UHFFFAOYSA-N

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