Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H11NO3 |
| Molecular Weight | 169.1778 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCC1=CC(O)=C(O)C=C1O
InChI
InChIKey=DIVDFFZHCJEHGG-UHFFFAOYSA-N
InChI=1S/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2
Oxidopamine (6-Hydroxydopamine) is an antagonist of the neurotransmitter dopamine with potential antineoplastic activity. 6-Hydroxydopamine (6-HOD) can be taken up by selective adrenergic terminals, thereby causing acute degeneration of adrenergic terminals that leads to depletion of norepinephrine, and of dopamine in the dopamine-sensitive sites. This agent is auto-oxidated at physiological pH that leads to the formation of reactive free radicals, thereby leading to cytotoxicity in neural cells. 6-Hydroxydopamine is often used to induce CNS and sympathetic neural lesions that model aging and various nervous disorders in animal systems. The growth of C-1300 neuroblastoma was markedly slowed in 6-hydroxydopamine-treated mice. The growth of the A-10 breast adenocarcinoma was also significantly retarded in 6-hydroxydopamine-treated mice but the growth of B-16 melanoma was not affected.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cocaine-induced hypertension: role of the peripheral sympathetic system. | 1999 Aug |
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| Role of sympathetic nervous system in experimental hypertension and diabetes mellitus. | 1999 Jan-Feb |
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| Regulation of EphB1 expression by dopamine signaling. | 2000 Dec 28 |
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| Effects of ropinirole on various parkinsonian models in mice, rats, and cynomolgus monkeys. | 2000 Mar |
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| Dopamine transporter function assessed by antisense knockdown in the rat: protection from dopamine neurotoxicity. | 2000 Sep 1 |
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| Enhanced axonal growth from fetal human bcl-2 transgenic mouse dopamine neurons transplanted to the adult rat striatum. | 2001 |
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| Inhibition of 6-hydroxydopamine-induced p53 expression and survival of neuroblastoma cells following interaction with astrocytes. | 2001 |
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| Co-transmitter function of ATP in central catecholaminergic neurons of the rat. | 2001 |
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| [3H]acetycholine release in rat striatal slices is not subject to dopamine heteroreceptor supersensitivity 30 months after 6-hydroxydopamine lesion of the substantia nigra. | 2001 Apr |
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| Delayed infusion of GDNF promotes recovery of motor function in the partial lesion model of Parkinson's disease. | 2001 Apr |
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| Alterations in cortical and basal ganglia levels of opioid receptor binding in a rat model of l-DOPA-induced dyskinesia. | 2001 Apr |
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| Changes in the gene expression of GABA(A) receptor alpha1 and alpha2 subunits and metabotropic glutamate receptor 5 in the basal ganglia of the rats with unilateral 6-hydroxydopamine lesion and embryonic mesencephalic grafts. | 2001 Apr |
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| Comparison of unilateral and bilateral intrastriatal 6-hydroxydopamine-induced axon terminal lesions: evidence for interhemispheric functional coupling of the two nigrostriatal pathways. | 2001 Apr 2 |
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| Effect of 6-hydroxydopamine or repeated amphetamine treatment on mesencephalic mRNA levels for AMPA glutamate receptor subunits in the rat. | 2001 Apr 20 |
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| Dorsal and ventral medullary catecholamine cell groups contribute differentially to systemic interleukin-1beta-induced hypothalamic pituitary adrenal axis responses. | 2001 Feb |
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| The sympathetic nervous system promotes carbon tetrachloride-induced liver cirrhosis in rats by suppressing apoptosis and enhancing the growth kinetics of regenerating hepatocytes. | 2001 Feb |
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| Norepinephrine modulates myelopoiesis after experimental thermal injury with sepsis. | 2001 Feb |
|
| Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
|
| Lymphocyte populations in Parkinson's disease and in rat models of parkinsonism. | 2001 Feb 1 |
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| Differential expression of GDNF, BDNF, and NT-3 in the aging nigrostriatal system following a neurotoxic lesion. | 2001 Feb 9 |
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| High frequency stimulation of the subthalamic nucleus increases the extracellular contents of striatal dopamine in normal and partially dopaminergic denervated rats. | 2001 Jan |
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| Fetal intra-nigral ventral mesencephalon and kidney tissue bridge transplantation restores the nigrostriatal dopamine pathway in hemi-parkinsonian rats. | 2001 Jan 19 |
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| Delta opioid peptide augments functional effects and intrastriatal graft survival of rat fetal ventral mesencephalic cells. | 2001 Jan-Feb |
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| Motor behavioural changes after intracerebroventricular injection of 6-hydroxydopamine in the rat: an animal model of Parkinson's disease. | 2001 Jul |
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| The ability of environmental context to facilitate psychomotor sensitization to amphetamine can be dissociated from its effect on acute drug responsiveness and on conditioned responding. | 2001 Jun |
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| Entopeduncular lesions facilitate and thalamic lesions depress spontaneous and drug-evoked motor behavior in the hemiparkinsonian rat. | 2001 Jun 1 |
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| Effect of chemical sympathectomy with 6-hydroxydopamine on osteoclast activity in the gerbilline middle ear bulla. | 2001 Mar |
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| Immunophilin ligands can prevent progressive dopaminergic degeneration in animal models of Parkinson's disease. | 2001 Mar |
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| 6-hydroxydopamine-induced lesions of dopaminergic neurons alter the function of postsynaptic cholinergic neurons without changing cytoskeletal proteins. | 2001 Mar |
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| Chemical sympathectomy increases the innate immune response and decreases the specific immune response in the spleen to infection with Listeria monocytogenes. | 2001 Mar 1 |
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| Neuroprotective effects of GDNF against 6-OHDA in young and aged rats. | 2001 Mar 30 |
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| The pasta matrix reaching task: a simple test for measuring skilled reaching distance, direction, and dexterity in rats. | 2001 Mar 30 |
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| Partial, graded losses of dopamine terminals in the rat caudate-putamen: an animal model for the study of compensatory adaptation in preclinical parkinsonism. | 2001 Mar 30 |
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| Disruption of dopaminergic neurotransmission in nucleus accumbens core inhibits the locomotor stimulant effects of nicotine and D-amphetamine in rats. | 2001 May |
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| Protective effects of 1 alpha,25-(OH)(2)D(3) against the neurotoxicity of glutamate and reactive oxygen species in mesencephalic culture. | 2001 May |
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| Dopamine cell degeneration induced by intraventricular administration of 6-hydroxydopamine in the rat: similarities with cell loss in parkinson's disease. | 2001 May |
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| Reaction of oxygen with 6-hydroxydopamine catalyzed by Cu, Fe, Mn, and V complexes: identification of a thermodynamic window for effective metal catalysis. | 2001 May 1 |
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| Enhancement of sensorimotor behavioral recovery in hemiparkinsonian rats with intrastriatal, intranigral, and intrasubthalamic nucleus dopaminergic transplants. | 2001 May 15 |
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| Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine. | 2001 May 25 |
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| BDNF controls dopamine D3 receptor expression and triggers behavioural sensitization. | 2001 May 3 |
|
| 6-hydroxydopamine increases hydroxyl free radical production and DNA damage in rat striatum. | 2001 May 8 |
Patents
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C66883
Created by
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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4624
Created by
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OXIDOPAMINE
Created by
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DTXSID0036768
Created by
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C1316
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4232
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SUB09524MIG
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100000083061
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8HW4YBZ748
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78741
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CHEMBL337702
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1199-18-4
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D016627
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214-842-3
Created by
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PRIMARY |
ACTIVE MOIETY
PARENT (METABOLITE TOXIC)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
