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H8876

5-Hydroxyindole-3-acetic acid

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

≥98% (HPLC), crystalline

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Synonym(s):

5-HIAA

Empirical Formula (Hill Notation):

C₁₀H₉NO₃

CAS Number:

54-16-0

Molecular Weight:

191.18

Beilstein:

168797

EC Number:

200-195-4

MDL number:

MFCD00005639

PubChem Substance ID:

24278130

NACRES:

NA.77

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)

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)

Investigation of the interaction between serotonin-related compounds and phenylboronate moieties in monolithic silica disk-packed spin columns.

Makoto Tsunoda et al.

Biomedical chromatography : BMC, 33(11), e4650-e4650 (2019-07-18)

Solid-phase extraction technologies are widely used for sample pretreatment in bioanalysis. Monolithic silica disk-packed spin columns modified with phenylboronate moieties have been developed for the selective extraction of cis-diol compounds such as catecholamines. However, in our preliminary studies, serotonin was

Combining tissue transcriptomics and urine metabolomics for breast cancer biomarker identification

Nam H, et al.

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

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Articles

Serotonin Synthesis and Metabolism

Serotonin (5-hydroxytryptamine) is principally found stored in three main cell types - i) serotonergic neurons in the CNS and in the intestinal myenteric plexus, ii) enterochromaffin cells in the mucosa of the gastrointestinal tract, and iii) in blood platelets. Metabolism of serotonin is carried out primarily by the outer mitochondrial membrane enzyme monoamine oxidase (MAO), which occurs as two molecular subtypes called MAO-A and MAO-B.

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