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=C(O)C(O)=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 |
|---|---|---|
| Degradation of natural polyphenols by methanogenic consortia enriched from digested municipal sludge. | 2001-08 |
|
| Continuous phencyclidine treatment induces schizophrenia-like hyperreactivity of striatal dopamine release. | 2001-08 |
|
| The MC4 receptor mediates alpha-MSH induced release of nucleus accumbens dopamine. | 2001-07-20 |
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| The role of dopamine receptors in regulating the size of axonal arbors. | 2001-07-15 |
|
| Biochemical and pathological study of endogenous 1-benzyl-1,2,3,4-tetrahydroisoquinoline-induced parkinsonism in the mouse. | 2001-07-13 |
|
| 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. | 2001-07 |
|
| Different action on dopamine catabolic pathways of two endogenous 1,2,3,4-tetrahydroisoquinolines with similar antidopaminergic properties. | 2001-07 |
|
| Oxygen inhalation enhances striatal dopamine metabolism and monoamineoxidase enzyme inhibition prevents it: a microdialysis study. | 2001-06-22 |
|
| Forced limb-use effects on the behavioral and neurochemical effects of 6-hydroxydopamine. | 2001-06-15 |
|
| Inhibition of cytochrome P450 2E1 induces an increase in extracellular dopamine in rat substantia nigra: a new metabolic pathway? | 2001-06-15 |
|
| Evidence against an essential role of endogenous brain dopamine in methamphetamine-induced dopaminergic neurotoxicity. | 2001-06 |
|
| Acute increases in monoamine release in the rat prefrontal cortex by the mGlu2/3 agonist LY379268 are similar in profile to risperidone, not locally mediated, and can be elicited in the presence of uptake blockade. | 2001-06 |
|
| Carbachol effect on carotid body dopamine in vitro release in response to hypoxia in adult and pup rabbit. | 2001-06 |
|
| Parkinson's disease--redox mechanisms. | 2001-06 |
|
| Dissociation of prolactin secretion from tuberoinfundibular dopamine activity in late pregnant rats. | 2001-06 |
|
| Nomifensine reveals age-related changes in K(+)-evoked striatal DA overflow in F344 rats. | 2001-05-30 |
|
| Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine. | 2001-05-25 |
|
| The role of dopamine in methylene blue-mediated inhibition of estradiol benzoate-induced anterior pituitary hyperplasia in rats. | 2001-05-25 |
|
| Lead intoxication during intrauterine life and lactation but not during adulthood reduces nucleus accumbens dopamine release as studied by brain microdialysis. | 2001-05-19 |
|
| BIA 3-202, a novel catechol-O-methyltransferase inhibitor, enhances the availability of L-DOPA to the brain and reduces its O-methylation. | 2001-05-18 |
|
| Neuroprotection by caffeine and A(2A) adenosine receptor inactivation in a model of Parkinson's disease. | 2001-05-15 |
|
| Chronic estrogen treatment replaces striatal dopaminergic function in ovariectomized rats. | 2001-05-11 |
|
| Striatal dopaminergic metabolism is increased by deep brain stimulation of the subthalamic nucleus in 6-hydroxydopamine lesioned rats. | 2001-05-11 |
|
| Prostaglandins play an important role in diurnal changes of tuberoinfundibular dopaminergic neuronal activity and prolactin secretion in ovariectomized, estrogen-treated rats. | 2001-05-01 |
|
| The role of dopamine in the nucleus accumbens and striatum during sexual behavior in the female rat. | 2001-05-01 |
|
| Sensitivity to MPTP is not increased in Parkinson's disease-associated mutant alpha-synuclein transgenic mice. | 2001-05 |
|
| Rapid changes in monoamine levels following administration of corticotropin-releasing factor or corticosterone are localized in the dorsomedial hypothalamus. | 2001-05 |
|
| 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. | 2001-04-30 |
|
| Generation and pharmacological analysis of M2 and M4 muscarinic receptor knockout mice. | 2001-04-27 |
|
| Selective dopaminergic vulnerability: 3,4-dihydroxyphenylacetaldehyde targets mitochondria. | 2001-04-15 |
|
| Oxalic acid stabilizes dopamine, serotonin, and their metabolites in automated liquid chromatography with electrochemical detection. | 2001-04-05 |
|
| Involvement of free radicals in MDMA-induced neurotoxicity in mice. | 2001-04 |
|
| The differential effect of angiotensin II and angiotensin 1-7 on norepinephrine, epinephrine, and dopamine concentrations in rat hypothalamus: the involvement of angiotensin receptors. | 2001-04 |
|
| Deprenyl stimulates the efflux of monoamines from the rat hypothalamus in vitro. | 2001-04 |
|
| Acute trazodone and quipazine treatment attenuates apomorphine-induced aggressive behaviour in male rats without major impact on emotional behaviour or monoamine content post mortem. | 2001-04 |
|
| Nitric oxide synthase inhibitors cause motor deficits in mice. | 2001-04 |
|
| Upregulation of striatal preproenkephalin gene expression occurs before the appearance of parkinsonian signs in 1-methyl-4-phenyl- 1,2,3,6-tetrahydropyridine monkeys. | 2001-04 |
|
| Involvement of central GABAergic neurons in basal and diurnal changes of tuberoinfundibular dopaminergic neuronal activity and prolactin secretion. | 2001-03-16 |
|
| Simultaneous measurement of dopamine and ascorbate at their physiological levels using voltammetric microprobe based on overoxidized poly(1,2-phenylenediamine)-coated carbon fiber. | 2001-03-15 |
|
| Inverse relationship between plasma epinephrine and testosterone levels during acute glucoprivation in healthy men. | 2001-03-09 |
|
| 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. | 2001-03-01 |
|
| Effects of intrastriatal infusion of D2 and D3 dopamine receptor preferring antagonists on dopamine release in rat dorsal striatum (in vivo microdialysis study). | 2001-03 |
|
| Food restriction-like effects of dietary dehydroepiandrosterone. Hypothalamic neurotransmitters and metabolites in male C57BL/6 and (C57BL/6 x DBA/2)F1 mice. | 2001-03 |
|
| 3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose. | 2001-03 |
|
| Increased sensitivity of dopamine systems following reproductive experience in rats. | 2001-03 |
|
| Biogenic aldehyde(s) derived from the action of monoamine oxidase may mediate the antidipsotropic effect of daidzin. | 2001-01-30 |
|
| Biphasic effects of selegiline on striatal dopamine: lack of effect on methamphetamine-induced dopamine depletion. | 2001-01 |
|
| Opposite genotype-dependent mesocorticolimbic dopamine response to stress. | 2001 |
|
| 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 |
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
Mon Mar 31 17:55:30 GMT 2025
by
admin
on
Mon Mar 31 17:55:30 GMT 2025
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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 | |||
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PARENT -> METABOLITE |
PLASMA; URINE
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