5-HYDROXYINDOLE-3-ACETIC ACID

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H9NO3
Molecular Weight	191.1834
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 5-HYDROXYINDOLE-3-ACETIC ACID

Structure Search

SMILES

OC(=O)CC1=CNC2=C1C=C(O)C=C2

InChI

InChIKey=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)

HIDE SMILES / InChI

Molecular Formula	C10H9NO3
Molecular Weight	191.1834
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Normal development of serotonergic neurons in mice lacking S100B.	2002-03-15	11872254
Dysregulation of hypothalamic serotonin turnover in diet-induced obese rats.	2002-03-08	11864622
Effects of intracerebroventricular injection of glucagon like peptide-1 and its related peptides on serotonin metabolism and on levels of amino acids in the rat hypothalamus.	2002-03-01	11852032
Dansyl-PQRamide, a possible neuropeptide FF receptor antagonist, induces conditioned place preference.	2002-03	11835998
Influence of leptin on neurotransmitter overflow from the rat brain in vitro.	2002-02-15	11786145
Effects of lifelong dietary exposure to genistein or nonylphenol on amphetamine-stimulated striatal dopamine release in male and female rats.	2002-02-12	11836070
Attenuating effects of the isolated rearing condition on increased brain serotonin and dopamine turnover elicited by novelty stress.	2002-02-01	11814401
Nighttime changes in norepinephrine and melatonin content and serotonin turnover in pineal glands of young and old rats injected with Freund's adjuvant.	2002-02	11880862
Effects of prenatal exposure to deltamethrin on forced swimming behavior, motor activity, and striatal dopamine levels in male and female rats.	2002-01-17	11792535
Reversal of stress-induced memory changes by moclobemide: the role of neurotransmitters.	2002-01-12	11785923
Inverse relationship of hippocampal serotonin to avoidance behavior, serotonergic activation by emotional stress differentiated by estrous cycle and surgical stress.	2002-01-07	11755688
[Serotonin metabolism in the brain during sexual motivation and activation of the murine hypothalamo-hypophyseal-testicular system].	2002-01-05	11764518
[Distribution of serotonin and its metabolites in the brain structures and immunosuppression in submissive mice].	2002-01	11868254
Pre- and postsynaptic responses to 1-(1-naphthylpiperazine) following adaptation to stress in rats.	2002-01	11853106
Post exercise hypotension is not mediated by the serotonergic system in borderline hypertensive individuals.	2002-01	11840227
Local blood serotonin and soluble P-selectin levels during percutaneous transluminal balloon angioplasty and primary stenting of the iliac artery.	2002-01	11821821
Primary renal carcinoid natural history of the disease for ten years: case report.	2002	11818030
Early experience and serotonin transporter gene variation interact to influence primate CNS function.	2002	11803458
Corticotropin-releasing hormone receptor type 1-deficiency enhances hippocampal serotonergic neurotransmission: an in vivo microdialysis study in mutant mice.	2002	11801362
Effects of acetaminophen on monoaminergic systems in the rat central nervous system.	2001-12	11770008
Measurement of plasma 5-hydroxyindoleacetic acid as a possible clinical surrogate marker for the action of antivascular agents.	2001-12	11718691
Characteristics of fluvoxamine-induced nausea.	2001-11-30	11728615
Aggressivity, suicide attempts, and depression: relationship to cerebrospinal fluid monoamine metabolite levels.	2001-11-15	11720697
Regional serotonin metabolism in the brain of transgenic mice lacking monoamine oxidase A.	2001-11-01	11746359
Role of monoamine oxidase inhibition and monoamine depletion in fenfluramine-induced neurotoxicity and serotonin release.	2001-11	11881977
Suppression of aggression in rainbow trout (Oncorhynchus mykiss) by dietary L-tryptophan.	2001-11	11807104
Examination of pineal indoles and 6-methoxy-2-benzoxazolinone for antioxidant and antimicrobial effects.	2001-11	11701394
Reaction of guanyl radicals in plasmid DNA with biological reductants: chemical repair of DNA damage produced by the direct effect of ionizing radiation.	2001-11	11683980
Effects of psychological stress on monoamine systems in subregions of the frontal cortex and nucleus accumbens of the rat.	2001-10-19	11597595
Serotonin, testosterone and alcohol in the etiology of domestic violence.	2001-10-10	11600187
Uraemia suppresses central dopaminergic metabolism and impairs motor activity in rats.	2001-10	11685308
Production and metabolism of serotonin (5-HT) by the human adrenal cortex: paracrine stimulation of aldosterone secretion by 5-HT.	2001-10	11600577
Profiling of tryptophan-related plasma indoles in patients with carcinoid tumors by automated, on-line, solid-phase extraction and HPLC with fluorescence detection.	2001-10	11568091
In-use stability of monoamine metabolites in human cerebrospinal fluid.	2001-09-05	11530989
Depression in Parkinson's disease: its prevalence, diagnosis, and neurochemical background.	2001-09	11697689
The mechanisms involved in the long-lasting neuroprotective effect of fluoxetine against MDMA ('ecstasy')-induced degeneration of 5-HT nerve endings in rat brain.	2001-09	11522596
Perianaesthetic risks and outcomes of abdominal surgery for metastatic carcinoid tumours.	2001-09	11517130
Disturbances of diurnal rhythms of biogenic amines contents in hypothalamic nuclei as an evidence of neurotropic effects of enterotropic carcinogen 1,2-dimethylhydrazine.	2001-08	11524628
Effects of dietary sucrose on hippocampal serotonin release: a microdialysis study in the freely-moving rat.	2001-08	11502227
Beta-amyloid(1-42)-induced cholinergic lesions in rat nucleus basalis bidirectionally modulate serotonergic innervation of the basal forebrain and cerebral cortex.	2001-08	11493031
Catecholamines in the heart and adrenal gland of the STZ-diabetic rat.	2001-07	11880922
Distal infantile neuroaxonal dystrophy--a new familial variant with perineuronal argyrophilic bodies.	2001-07	11547955
Interleukin-6 involvement in antidepressant action of Hypericum perforatum.	2001-07	11518082
Evidence that the branched-chain amino acid L-valine prevents exercise-induced release of 5-HT in rat hippocampus.	2001-07	11510866
Brain monoaminergic activity in rainbow trout selected for high and low stress responsiveness.	2001-04	11641559
[Disruption of circadian rhythms of biogenic amines in rat hypothalamus upon administration of 1,2-dimethylhydrazine].	2001	11785105
Serotonin and 5-hydroxyindole-acetic acid.	2001	11763663
Clinical significance of blood chromogranin A measurement in neuroendocrine tumours.	2001	11762355
Inhibition of K(+)-evoked release of rat striatal 5-hydroxytryptamine by an atypical antidepressant: trazodone.	2001	11490181
Intraspinal pressure influences CSF disposition of tryptophan and 5-HIAA.	2001	11490176

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:36:08 GMT 2025` Edited by `admin` on `Mon Mar 31 19:36:08 GMT 2025`
Record UNII	YHC763JY1P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5-HYDROXYINDOLE-3-ACETIC ACID

Systematic Name

English

NSC-90432

Preferred Name

English

1H-INDOLE-3-ACETIC ACID, 5-HYDROXY-

Common Name

English

5-HYDROXYINDOLEACETIC ACID

Systematic Name

English

HYDROXYINDOLEACETIC ACID

Systematic Name

English

5-HYDROXYINDOLE ACETIC ACID

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1937