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Merck
CN

H8876

5-Hydroxyindole-3-acetic acid

≥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
NACRES:
NA.77
PubChem Substance ID:
24278130
UNSPSC Code:
12352106
EC Number:
200-195-4
MDL number:
MFCD00005639
Beilstein/REAXYS Number:
168797

Key Documents

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Product Name

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

Quality Level

200

InChI key

DUUGKQCEGZLZNO-UHFFFAOYSA-N

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)

SMILES string

OC(=O)Cc1c[nH]c2ccc(O)cc12

assay

≥98% (HPLC)

form

crystalline

color

white to purple

mp

161-164 °C (dec.) (lit.)

storage temp.

−20°C

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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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.

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).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN0749
BCCL3424
BCCL9267
BCCJ4414
BCCH5209

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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)
Combining tissue transcriptomics and urine metabolomics for breast cancer biomarker identification
Nam H, et al.
Bioinformatics, 25(23), 3151-3157 (2009)
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
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)
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 & Metabolism

Serotonin is stored in cells and metabolized by MAO, influencing CNS, GI, and platelet functions.

血清素合成及代谢

血清素（5-羟色胺）主要存在于三种主要细胞类型中：i）中杻神经系统（CNS）和肠肌间神经丛中的血清素能神经元，ii）胃肠道粘膜中的肠嗜铬细胞，和iii）血小板。血清素的代谢主要通过外部线粒体膜酶单胺氧化酶（MAO）进行，它以两种分子亚型存在，分别称为MAO-A和MAO-B。

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