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H8876

5-Hydroxyindole-3-acetic acid

Name: 5-Hydroxyindole-3-acetic acid
Brand: SIGMA

≥98% (HPLC), crystalline

Synonym(s):

5-HIAA

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₉NO₃

CAS Number:

54-16-0

Molecular Weight:

191.18

Beilstein:

168797

EC Number:

200-195-4

MDL number:

MFCD00005639

UNSPSC Code:

12352106

PubChem Substance ID:

24278130

NACRES:

NA.77

product name

5-Hydroxyindole-3-acetic acid, ≥98% (HPLC), crystalline

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)

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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).

Biochem/physiol Actions

Major serotonin metabolite.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Combining tissue transcriptomics and urine metabolomics for breast cancer biomarker identification

Nam H, et al.

Bioinformatics, 25(23), 3151-3157 (2009)

Lower CSF HVA and 5-HIAA in bipolar disorder type 1 with a history of childhood ADHD

Ryden E, et al.

Journal of neural transmission (Vienna, Austria : 1996), 116(12), 1667-1674 (2009)

Chronic high dose of captopril induces depressive-like behaviors in mice: possible mechanism of regulatory T cell in depression

Park HS, et al.

Oncotarget, 8(42), 72528-72543 (2017)

Progression and recovery of Parkinsonism in a chronic progressive MPTP-induction model in the marmoset without persistent molecular and cellular damage

Franke SK, et al.

Neuroscience, 312, 247-259 (2016)

Serotonergic reinforcement of intestinal barrier function is impaired in irritable bowel syndrome.

D Keszthelyi et al.

Alimentary pharmacology & therapeutics, 40(4), 392-402 (2014-06-20)

Alterations in serotonergic (5-HT) metabolism and/or intestinal integrity have been associated with irritable bowel syndrome (IBS). To assess the effects of the precursor of 5-HT, 5-hydroxytryptophan (5-HTP), on mucosal 5-HT availability and intestinal integrity, and to assess potential differences between

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