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H8876 Sigma-Aldrich

5-Hydroxyindole-3-acetic acid

≥98% (HPLC), crystalline

Synonym: 5-HIAA

  • CAS Number 54-16-0

  • Empirical Formula (Hill Notation) C10H9NO3

  • Molecular Weight 191.18

  •  Beilstein/REAXYS Number 168797

  •  EC Number 200-195-4

  •  MDL number MFCD00005639

  •  PubChem Substance ID 24278130

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, H,
Quality Level   200
assay   ≥98% (HPLC)
form   crystalline
color   white to purple
mp   161-164 °C (dec.) (lit.)
storage temp.   −20°C
SMILES string   OC(=O)Cc1c[nH]c2ccc(O)cc12
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)
InChI key   DUUGKQCEGZLZNO-UHFFFAOYSA-N
Gene Information   human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242), HTR4(3360), HTR5A(3361), HTR5B(645694), HTR6(3362), HTR7(3363)

Description

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).

Application

5-Hydroxyindole-3-acetic acid has been used as standard for the measurement of 5-HIAA in the brain tissue of mice using high performance liquid chromatography (HPLC).

Packaging

1 g in poly bottle

500 mg in poly tube

100 mg in poly bottle

Biochem/physiol Actions

Major serotonin metabolite.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
NL3650000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Indoles

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MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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