Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H8O4 |
| Molecular Weight | 168.1467 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC1=CC(O)=C(O)C=C1
InChI
InChIKey=CFFZDZCDUFSOFZ-UHFFFAOYSA-N
InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
| Molecular Formula | C8H8O4 |
| Molecular Weight | 168.1467 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
3, 4-dihydroxyphenylacetic acid (DOPAC) is a neuronal metabolite of dopamine (DA). DA undergoes monoamine oxidase-catalyzed oxidative deamination to 3,4-dihydroxyphenylacetaldehyde (DOPAL), which is metabolized primarily to 3,4-dihydroxyphenylacetic acid (DOPAC) via aldehyde dehydrogenase, ALDH2. DOPAC exhibits the antiproliferative effect in colon cancer cells. In addition, DOPAC enhances not only the total ALDH activity but also the gene expression of ALDH1A1, ALDH2, and ALDH3A1 in a concentration-dependent manner. The pretreatment of DOPAC completely protects the cells from the acetaldehyde-induced cytotoxicity, thus DOPAC acts as a potential ALDH inducer to prevent the alcohol-induced abnormal reaction.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Renal dopaminergic mechanisms in renal parenchymal diseases and hypertension. | 2001 |
|
| The central catechol-O-methyltransferase inhibitor tolcapone increases striatal hydroxyl radical production in L-DOPA/carbidopa treated rats. | 2001 |
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| Effect of GBR 12909 and fluoxetine on the acute and long term changes induced by MDMA ('ecstasy') on the 5-HT and dopamine concentrations in mouse brain. | 2001 |
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| Acute trazodone and quipazine treatment attenuates apomorphine-induced aggressive behaviour in male rats without major impact on emotional behaviour or monoamine content post mortem. | 2001 Apr |
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| Nitric oxide synthase inhibitors cause motor deficits in mice. | 2001 Apr |
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| 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 |
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| Changes in endogenous monoamines in aged rats. | 2001 Apr |
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| Selective dopaminergic vulnerability: 3,4-dihydroxyphenylacetaldehyde targets mitochondria. | 2001 Apr 15 |
|
| Parallel induction of the formation of dopamine and its metabolites with induction of tyrosine hydroxylase expression in foetal rat and human cerebral cortical cells by brain-derived neurotrophic factor and glial-cell derived neurotrophic factor. | 2001 Apr 30 |
|
| Oxalic acid stabilizes dopamine, serotonin, and their metabolites in automated liquid chromatography with electrochemical detection. | 2001 Apr 5 |
|
| Degradation of natural polyphenols by methanogenic consortia enriched from digested municipal sludge. | 2001 Aug |
|
| Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
|
| Changes in striatal electroencephalography and neurochemistry induced by kainic acid seizures are modified by dopamine receptor antagonists. | 2001 Feb 16 |
|
| Biphasic effects of selegiline on striatal dopamine: lack of effect on methamphetamine-induced dopamine depletion. | 2001 Jan |
|
| High frequency stimulation of the subthalamic nucleus increases the extracellular contents of striatal dopamine in normal and partially dopaminergic denervated rats. | 2001 Jan |
|
| Monoamine compounds in cerebrospinal fluid of healthy subjects punctured without preceding strict bed rest: a pilot study. | 2001 Jan |
|
| Changes of biogenic amine levels in haemolymph during diapausing and non-diapausing status in Pieris brassicae L. | 2001 Jan |
|
| Nicotine prevents striatal dopamine loss produced by 6-hydroxydopamine lesion in the substantia nigra. | 2001 Jan 12 |
|
| Behavioral activation in rats requires endogenous ascorbate release in striatum. | 2001 Jan 15 |
|
| Significance of glutamate and dopamine neurons in the ventral pallidum in the expression of behavioral sensitization to amphetamine. | 2001 Jan 19 |
|
| Biogenic aldehyde(s) derived from the action of monoamine oxidase may mediate the antidipsotropic effect of daidzin. | 2001 Jan 30 |
|
| Cloning of the genes for a 4-sulphocatechol-oxidizing protocatechuate 3,4-dioxygenase from Hydrogenophaga intermedia S1 and identification of the amino acid residues responsible for the ability to convert 4-sulphocatechol. | 2001 Jul |
|
| The MC4 receptor mediates alpha-MSH induced release of nucleus accumbens dopamine. | 2001 Jul 20 |
|
| Carbachol effect on carotid body dopamine in vitro release in response to hypoxia in adult and pup rabbit. | 2001 Jun |
|
| Parkinson's disease--redox mechanisms. | 2001 Jun |
|
| Dissociation of prolactin secretion from tuberoinfundibular dopamine activity in late pregnant rats. | 2001 Jun |
|
| Forced limb-use effects on the behavioral and neurochemical effects of 6-hydroxydopamine. | 2001 Jun 15 |
|
| Inhibition of cytochrome P450 2E1 induces an increase in extracellular dopamine in rat substantia nigra: a new metabolic pathway? | 2001 Jun 15 |
|
| Food restriction-like effects of dietary dehydroepiandrosterone. Hypothalamic neurotransmitters and metabolites in male C57BL/6 and (C57BL/6 x DBA/2)F1 mice. | 2001 Mar |
|
| 3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose. | 2001 Mar |
|
| Increased sensitivity of dopamine systems following reproductive experience in rats. | 2001 Mar |
|
| Seizure activity and hyperthermia potentiate the increases in dopamine and serotonin extracellular levels in the amygdala during exposure to d-amphetamine. | 2001 Mar |
|
| Expression of sensitization to amphetamine and dynamics of dopamine neurotransmission in different laminae of the rat medial prefrontal cortex. | 2001 Mar |
|
| Ovulation delay induced by blockade of the cholinergic system on dioestrus-1, is related to changes in dopaminergic activity of the preoptic anterior-hypothalamic area of the rat. | 2001 Mar 1 |
|
| Simultaneous measurement of dopamine and ascorbate at their physiological levels using voltammetric microprobe based on overoxidized poly(1,2-phenylenediamine)-coated carbon fiber. | 2001 Mar 15 |
|
| Increased extracellular DA and normal evoked DA release in the rat striatum after a partial lesion of the substantia nigra. | 2001 Mar 2 |
|
| Sensitivity to MPTP is not increased in Parkinson's disease-associated mutant alpha-synuclein transgenic mice. | 2001 May |
|
| Rapid changes in monoamine levels following administration of corticotropin-releasing factor or corticosterone are localized in the dorsomedial hypothalamus. | 2001 May |
|
| Nicotine receptor inactivation decreases sensitivity to cocaine. | 2001 May |
|
| Prostaglandins play an important role in diurnal changes of tuberoinfundibular dopaminergic neuronal activity and prolactin secretion in ovariectomized, estrogen-treated rats. | 2001 May 1 |
|
| The role of dopamine in the nucleus accumbens and striatum during sexual behavior in the female rat. | 2001 May 1 |
|
| Chronic estrogen treatment replaces striatal dopaminergic function in ovariectomized rats. | 2001 May 11 |
|
| Striatal dopaminergic metabolism is increased by deep brain stimulation of the subthalamic nucleus in 6-hydroxydopamine lesioned rats. | 2001 May 11 |
|
| Neuroprotection by caffeine and A(2A) adenosine receptor inactivation in a model of Parkinson's disease. | 2001 May 15 |
|
| BIA 3-202, a novel catechol-O-methyltransferase inhibitor, enhances the availability of L-DOPA to the brain and reduces its O-methylation. | 2001 May 18 |
|
| Lead intoxication during intrauterine life and lactation but not during adulthood reduces nucleus accumbens dopamine release as studied by brain microdialysis. | 2001 May 19 |
|
| Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine. | 2001 May 25 |
|
| The role of dopamine in methylene blue-mediated inhibition of estradiol benzoate-induced anterior pituitary hyperplasia in rats. | 2001 May 25 |
Sample Use Guides
In Vitro Use Guide
Curator's Comment: 3,4-Dihydroxyphenylacetic acid (DOPAC) was shown to enhance not only the total ALDH activity, but also the gene expression of ALDH1A1, ALDH2 and ALDH3A1 in a concentration-dependent manner. DOPAC simultaneously stimulated the nuclear translocation of NFE2-related factor 2 and aryl hydrocarbon receptor. The pretreatment of DOPAC completely protected the cells from the acetaldehyde-induced cytotoxicity. The present study suggested that DOPAC acts as a potential ALDH inducer to prevent the alcohol-induced abnormal reaction.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:52:52 UTC 2023
by
admin
on
Wed Jul 05 22:52:52 UTC 2023
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| Record UNII |
KEX5N0R4N5
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| Record Status |
Validated (UNII)
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| Record Version |
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102-32-9
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203-024-1
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73191
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3,4-Dihydroxyphenylacetic acid
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41941
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DB01702
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DTXSID9074430
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KEX5N0R4N5
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547
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> METABOLITE |
Excretion of 3,4-Dihydroxyphenylacetic acid in the urine of human subjects (n=6, 0-24hr total) after rutin (176 micromoles) supplemented tomato juice; Unit: micromoles
IN-VIVO
URINE
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PARENT -> METABOLITE |
PLASMA; URINE
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