Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H11NO3 |
| Molecular Weight | 169.1782 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C(CN)c1cc(c(cc1O)O)O
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
| Molecular Formula | C8H11NO3 |
| Molecular Weight | 169.1782 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Enhanced axonal growth from fetal human bcl-2 transgenic mouse dopamine neurons transplanted to the adult rat striatum. | 2001 |
|
| Intrapallidal dopamine restores motor deficits induced by 6-hydroxydopamine in the rat. | 2001 |
|
| Dopaminergic mRNA expression in the intact substantia nigra of unilaterally 6-OHDA-lesioned and grafted rats: an in situ hybridization study. | 2001 |
|
| Inhibition of 6-hydroxydopamine-induced p53 expression and survival of neuroblastoma cells following interaction with astrocytes. | 2001 |
|
| Unilateral dopamine depletion increases expression of the 2A subunit of the N-methyl-D-aspartate receptor in enkephalin-positive and enkephalin-negative neurons. | 2001 |
|
| Subthalamic infusion of an NMDA antagonist prevents basal ganglia metabolic changes and nigral degeneration in a rodent model of Parkinson's disease. | 2001 Apr |
|
| Dose-related neuroprotective effects of chronic nicotine in 6-hydroxydopamine treated rats, and loss of neuroprotection in alpha4 nicotinic receptor subunit knockout mice. | 2001 Apr |
|
| Alterations in cortical and basal ganglia levels of opioid receptor binding in a rat model of l-DOPA-induced dyskinesia. | 2001 Apr |
|
| Rescue from death but not from functional impairment: caspase inhibition protects dopaminergic cells against 6-hydroxydopamine-induced apoptosis but not against the loss of their terminals. | 2001 Apr |
|
| A nitric oxide-dopamine link pathway in organum vasculosum laminae terminalis of rat brain exerts control over blood pressure. | 2001 Apr |
|
| Lesion of the bulbospinal noradrenergic pathways blocks desipramine-induced inhibition of the C-fiber evoked nociceptive reflex in rats. | 2001 Apr 13 |
|
| Growth and functional efficacy of intrastriatal nigral transplants depend on the extent of nigrostriatal degeneration. | 2001 Apr 15 |
|
| Effect of 6-hydroxydopamine or repeated amphetamine treatment on mesencephalic mRNA levels for AMPA glutamate receptor subunits in the rat. | 2001 Apr 20 |
|
| Time-course of changes in firing rates and firing patterns of subthalamic nucleus neuronal activity after 6-OHDA-induced dopamine depletion in rats. | 2001 Apr 27 |
|
| Ribozyme-mediated inhibition of caspase-3 activity reduces apoptosis induced by 6-hydroxydopamine in PC12 cells. | 2001 Apr 27 |
|
| NMDA glutamate receptor stimulation is required for the expression of D2 dopamine mediated responses in apomorphine primed 6-hydroxydopamine lesioned rats. | 2001 Apr 6 |
|
| Microencapsulated bovine chromaffin cell xenografts into hemiparkinsonian rats: a drug-induced rotational behavior and histological changes analysis. | 2001 Feb |
|
| Molecular mechanism in activation of glutathione system by ropinirole, a selective dopamine D2 agonist. | 2001 Jan |
|
| Alteration of spontaneous firing rate of primary myelinated afferents by ATP in adjuvant-induced inflamed rats. | 2001 Jan 15 |
|
| Delta opioid peptide augments functional effects and intrastriatal graft survival of rat fetal ventral mesencephalic cells. | 2001 Jan-Feb |
|
| Motor behavioural changes after intracerebroventricular injection of 6-hydroxydopamine in the rat: an animal model of Parkinson's disease. | 2001 Jul |
|
| Bcl-2 and GDNF delivered by HSV-mediated gene transfer act additively to protect dopaminergic neurons from 6-OHDA-induced degeneration. | 2001 Jun |
|
| 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 |
|
| Generation of dopaminergic neurons in the adult brain from mesencephalic precursor cells labeled with a nestin-GFP transgene. | 2001 Jun 1 |
|
| Free 3-nitrotyrosine causes striatal neurodegeneration in vivo. | 2001 Jun 1 |
|
| Entopeduncular lesions facilitate and thalamic lesions depress spontaneous and drug-evoked motor behavior in the hemiparkinsonian rat. | 2001 Jun 1 |
|
| Serotonin, norepinephrine and dopamine involvement in the antidepressant action of hypericum perforatum. | 2001 Mar |
|
| Effect of chemical sympathectomy with 6-hydroxydopamine on osteoclast activity in the gerbilline middle ear bulla. | 2001 Mar |
|
| Immunophilin ligands can prevent progressive dopaminergic degeneration in animal models of Parkinson's disease. | 2001 Mar |
|
| Adrenergic hyperactivity and metanephrine excess in the nucleus accumbens after prefrontocortical dopamine depletion. | 2001 Mar |
|
| Motor stimulant effects of the adenosine A2A receptor antagonist SCH 58261 do not develop tolerance after repeated treatments in 6-hydroxydopamine-lesioned rats. | 2001 Mar 1 |
|
| Modulation of visceral nociceptive responses of rat spinal dorsal horn neurons by sympathectomy. | 2001 Mar 26 |
|
| Neuroprotective effects of GDNF against 6-OHDA in young and aged rats. | 2001 Mar 30 |
|
| The pasta matrix reaching task: a simple test for measuring skilled reaching distance, direction, and dexterity in rats. | 2001 Mar 30 |
|
| 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 |
|
| Disruption of dopaminergic neurotransmission in nucleus accumbens core inhibits the locomotor stimulant effects of nicotine and D-amphetamine in rats. | 2001 May |
|
| Protective effects of 1 alpha,25-(OH)(2)D(3) against the neurotoxicity of glutamate and reactive oxygen species in mesencephalic culture. | 2001 May |
|
| Sustained extracellular signal-regulated kinase activation by 6-hydroxydopamine: implications for Parkinson's disease. | 2001 May |
|
| Neuroimmunophilin ligands exert neuroregeneration and neuroprotection in midbrain dopaminergic neurons. | 2001 May |
|
| Dopamine cell degeneration induced by intraventricular administration of 6-hydroxydopamine in the rat: similarities with cell loss in parkinson's disease. | 2001 May |
|
| Coadministration of (-)-OSU6162 with l-DOPA normalizes preproenkephalin mRNA expression in the sensorimotor striatum of primates with unilateral 6-OHDA lesions. | 2001 May |
|
| Glial cell line-derived neurotrophic factor (GDNF) gene delivery protects dopaminergic terminals from degeneration. | 2001 May |
|
| Diminished survival of mesencephalic dopamine neurons grafted into aged hosts occurs during the immediate postgrafting interval. | 2001 May |
|
| Intrasubthalamic injection of 6-hydroxydopamine induces changes in the firing rate and pattern of subthalamic nucleus neurons in the rat. | 2001 May |
|
| 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 |
|
| Striatal dopaminergic metabolism is increased by deep brain stimulation of the subthalamic nucleus in 6-hydroxydopamine lesioned rats. | 2001 May 11 |
|
| Enhancement of sensorimotor behavioral recovery in hemiparkinsonian rats with intrastriatal, intranigral, and intrasubthalamic nucleus dopaminergic transplants. | 2001 May 15 |
|
| Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine. | 2001 May 25 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 14:16:23 UTC 2021
by
admin
on
Sat Jun 26 14:16:23 UTC 2021
|
| Record UNII |
8HW4YBZ748
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
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Official Name | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
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Systematic Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C66883
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
4624
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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PRIMARY | |||
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OXIDOPAMINE
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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PRIMARY | |||
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1199-18-4
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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PRIMARY | |||
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C1316
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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PRIMARY | |||
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4232
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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PRIMARY | |||
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SUB09524MIG
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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PRIMARY | |||
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8HW4YBZ748
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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PRIMARY | |||
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CHEMBL337702
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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PRIMARY | |||
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1199-18-4
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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PRIMARY | |||
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D016627
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
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PRIMARY | |||
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214-842-3
Created by
admin on Sat Jun 26 14:16:24 UTC 2021 , Edited by admin on Sat Jun 26 14:16:24 UTC 2021
|
PRIMARY |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
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PARENT -> METABOLITE TOXIC |
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ACTIVE MOIETY |
