HOMOVANILLIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10O4
Molecular Weight	182.1733
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(CC(O)=O)=CC=C1O

InChI

InChIKey=QRMZSPFSDQBLIX-UHFFFAOYSA-N

InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)

HIDE SMILES / InChI

Molecular Formula	C9H10O4
Molecular Weight	182.1733
Charge	0
Count

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxidase C1A 3 Target ID: P00433 Gene ID: NA Gene Symbol: PRXC1A Target Organism: Armoracia rusticana (Horseradish) (Armoracia laphatifolia) Sources: https://www.ncbi.nlm.nih.gov/pubmed/5634544	Substrate 656
Target ID: Flucose oxidase, fungal Sources: https://www.ncbi.nlm.nih.gov/pubmed/5634544	Substrate 656
Xanthine dehydrogenase 32 Target ID: CHEMBL3649 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5634544	Substrate 656

PubMed

Title	Date	PubMed
Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment.	1979 Aug 8	115032
CSF studies in violent offenders. I. 5-HIAA as a negative and HVA as a positive predictor of psychopathy.	2001	11515752
Opposite genotype-dependent mesocorticolimbic dopamine response to stress.	2001	11440796
Intracerebral administration of 2,4-diclorophenoxyacetic acid induces behavioral and neurochemical alterations in the rat brain.	2001 Apr	11405254
Nitric oxide synthase inhibitors cause motor deficits in mice.	2001 Apr	11313158
Upregulation of striatal preproenkephalin gene expression occurs before the appearance of parkinsonian signs in 1-methyl-4-phenyl- 1,2,3,6-tetrahydropyridine monkeys.	2001 Apr	11300729
Determination of homovanillic acid in urine by stable isotope dilution and electrospray tandem mass spectrometry.	2001 Apr	11282092
Transgenic ALS mice show increased vulnerability to the mitochondrial toxins MPTP and 3-nitropropionic acid.	2001 Apr	11259123
Oxalic acid stabilizes dopamine, serotonin, and their metabolites in automated liquid chromatography with electrochemical detection.	2001 Apr 5	11334358
Site-specific activation of dopamine and serotonin transmission by aniracetam in the mesocorticolimbic pathway of rats.	2001 Apr 6	11282361
Catecholamines in patients with 22q11.2 deletion syndrome and the low-activity COMT polymorphism.	2001 Aug 14	11502905
Effect of intracerebral 6-nitronoradrenaline, an endogenous catechol-O-methyltransferase (COMT) inhibitor, on striatal dopamine metabolism in anaesthetised rats.	2001 Aug 15	11489299
The cannabinoid CB(1) receptor antagonist SR141716A increases norepinephrine outflow in the rat anterior hypothalamus.	2001 Aug 31	11527547
Developmental changes in cerebrospinal fluid concentrations of monoamine-related substances in patients with dentatorubral-pallidoluysian atrophy.	2001 Feb	11292229
Evaluation of catecholamine metabolites, mIBG scan, and bone marrow cytology as response markers in stage 4 neuroblastoma.	2001 Jan	11464889
Observation of untreated patients with neuroblastoma detected by mass screening: a "wait and see" pilot study.	2001 Jan	11464874
Striatal dopamine sensitization to D-amphetamine in periadolescent but not in adult rats.	2001 Jan	11274716
[Mexidol potentiates antiparkinsonian effect of L-DOPA in MPTP-induced parkinsonism model].	2001 Jan-Feb	11544797
Plasma homovanillic acid in untreated schizophrenia--relationship with symptomatology and sex.	2001 Jan-Feb	11287053
Distal infantile neuroaxonal dystrophy--a new familial variant with perineuronal argyrophilic bodies.	2001 Jul	11547955
The effects of extracts from St. John's Wort and Kava Kava on brain neurotransmitter levels in the mouse.	2001 Jul	11518062
Different action on dopamine catabolic pathways of two endogenous 1,2,3,4-tetrahydroisoquinolines with similar antidopaminergic properties.	2001 Jul	11432977
Biochemical alterations during medication withdrawal in Parkinson's disease with and without neuroleptic malignant-like syndrome.	2001 Jul	11413275
Effects of repeated morphine treatment on metabolism of cerebral dopamine and serotonin in alcohol-preferring AA and alcohol-avoiding ANA rats.	2001 Jul-Aug	11468126
Long term effects of Toki-shakuyaku-san on brain dopamine and nerve growth factor in olfactory-bulb-lesioned mice.	2001 Jun	11459120
A novel neurodevelopmental syndrome responsive to 5-hydroxytryptophan and carbidopa.	2001 Jun	11386854
Neurofunctional effects of developmental alcohol exposure in alcohol-preferring and alcohol-nonpreferring rats.	2001 Jun	11331149
Accumbens dopamine mechanisms in sucrose intake.	2001 Jun 15	11516413
Forced limb-use effects on the behavioral and neurochemical effects of 6-hydroxydopamine.	2001 Jun 15	11404429
Inhibition of cytochrome P450 2E1 induces an increase in extracellular dopamine in rat substantia nigra: a new metabolic pathway?	2001 Jun 15	11309845
Oxygen inhalation enhances striatal dopamine metabolism and monoamineoxidase enzyme inhibition prevents it: a microdialysis study.	2001 Jun 22	11430914
Effect of embryonic knock-down of GABAA receptors on the levels of monoamines and their metabolites in the CNS of the mouse.	2001 Jun 22	11406127
Effects of intrastriatal infusion of D2 and D3 dopamine receptor preferring antagonists on dopamine release in rat dorsal striatum (in vivo microdialysis study).	2001 Mar	11401421
Infantile-onset paroxysmal dystonia: a diagnostic dilemma.	2001 Mar	11305692
Central nervous system stimulatory action from the root extract of Plumbago zeylanica in rats.	2001 Mar	11268117
Effects of intraplantar injection of carrageenan on central dopamine release.	2001 Mar 1	11306190
Limbic dopaminergic adaptation to a stressful stimulus in a rat model of depression.	2001 Mar 30	11277971
Inverse relationship between plasma epinephrine and testosterone levels during acute glucoprivation in healthy men.	2001 Mar 9	11292066
[Involvement of dopaminergic systems in the functional specialization of brain areas during formation of aggressive and submissive behavior in mice].	2001 Mar-Apr	11548601
Sensitivity to MPTP is not increased in Parkinson's disease-associated mutant alpha-synuclein transgenic mice.	2001 May	11359883
Striatal dopaminergic and serotonergic markers in human heroin users.	2001 May	11282256
The role of dopamine in the nucleus accumbens and striatum during sexual behavior in the female rat.	2001 May 1	11312308
Chronic estrogen treatment replaces striatal dopaminergic function in ovariectomized rats.	2001 May 11	11334794
Striatal dopaminergic metabolism is increased by deep brain stimulation of the subthalamic nucleus in 6-hydroxydopamine lesioned rats.	2001 May 11	11323111
Nomifensine reveals age-related changes in K(+)-evoked striatal DA overflow in F344 rats.	2001 May-Jun	11378257
Effect of clonazepam treatment on antipsychotic drug-induced Meige syndrome and changes in plasma levels of GABA, HVA, and MHPG during treatment.	2001 Oct	11555353
Effect of chronic protein restriction on motor co-ordination and brain neurotransmitters in albino rats.	2001 Oct	11524142
Aging increases the susceptiblity to methamphetamine-induced dopaminergic neurotoxicity in rats: correlation with peroxynitrite production and hyperthermia.	2001 Sep	11553669
Heart failure, aging, and renal synthesis of dopamine.	2001 Sep	11532681
In-use stability of monoamine metabolites in human cerebrospinal fluid.	2001 Sep 5	11530989

Patents

Substance Class	Chemical Created by `admin` on `Thu Jul 06 01:42:28 UTC 2023` Edited by `admin` on `Thu Jul 06 01:42:28 UTC 2023`
Record UNII	X77S6GMS36
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HOMOVANILLIC ACID

Systematic Name

English

HVA

Common Name

English

4-HYDROXY-3-METHOXY-.ALPHA.-TOLUIC ACID

Systematic Name

English

VANILACETIC ACID

Common Name

English

HOMOVANILLIC ACID [MI]

Common Name

English

NSC-16682

Code

English

(4-HYDROXY-3-METHOXYPHENYL)ACETIC ACID

Systematic Name

English

HMDB00118

Code

English

3-METHOXY-4-HYDROXYPHENYLACETIC ACID

Systematic Name

English

4-HYDROXY-3-METHOXYBENZENEACETIC ACID

Systematic Name

English

Code System Code Type Description

FDA UNII

X77S6GMS36