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
Molecular Formula | C8H11NO3 |
Molecular Weight | 169.1778 |
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL338 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562944 |
12.0 nM [Ki] | ||
Target ID: CHEMBL304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562944 |
51.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Striatal fosB expression is causally linked with l-DOPA-induced abnormal involuntary movements and the associated upregulation of striatal prodynorphin mRNA in a rat model of Parkinson's disease. | 1999 Dec |
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Regulation of EphB1 expression by dopamine signaling. | 2000 Dec 28 |
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Embryonic ventral mesencephalic grafts improve levodopa-induced dyskinesia in a rat model of Parkinson's disease. | 2000 Jul |
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Effects of ropinirole on various parkinsonian models in mice, rats, and cynomolgus monkeys. | 2000 Mar |
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Delivery of a GDNF gene into the substantia nigra after a progressive 6-OHDA lesion maintains functional nigrostriatal connections. | 2000 Nov |
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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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Unilateral dopamine depletion increases expression of the 2A subunit of the N-methyl-D-aspartate receptor in enkephalin-positive and enkephalin-negative neurons. | 2001 |
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Septal cholinergic neurons suppress seizure development in hippocampal kindling in rats: comparison with noradrenergic neurons. | 2001 |
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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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A nitric oxide-dopamine link pathway in organum vasculosum laminae terminalis of rat brain exerts control over blood pressure. | 2001 Apr |
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Retrograde tracing techniques influence reported death rates of adult rat nigrostriatal neurons. | 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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Lesion of the bulbospinal noradrenergic pathways blocks desipramine-induced inhibition of the C-fiber evoked nociceptive reflex in rats. | 2001 Apr 13 |
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Circadian rhythm of drinking and running-wheel activity in rats with 6-hydroxydopamine lesions of the ventral tegmental area. | 2001 Apr 27 |
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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 |
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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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Melatonin protects against 6-OHDA-induced neurotoxicity in rats: a role for mitochondrial complex I activity. | 2001 Jan |
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The central aromatic amino acid DOPA decarboxylase inhibitor, NSD-1015, does not inhibit L-DOPA-induced circling in unilateral 6-OHDA-lesioned-rats. | 2001 Jan |
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Injury induced c-Jun expression and phosphorylation in the dopaminergic nigral neurons of the rat: correlation with neuronal death and modulation by glial-cell-line-derived neurotrophic factor. | 2001 Jan |
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Regulation of GAP-43 protein and mRNA in nigrostriatal dopaminergic neurons after the partial destruction of dopaminergic terminals with intrastriatal 6-hydroxydopamine. | 2001 Jan |
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The small molecule FKBP ligand GPI 1046 induces partial striatal re-innervation after intranigral 6-hydroxydopamine lesion in rats. | 2001 Jan 12 |
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Alteration of spontaneous firing rate of primary myelinated afferents by ATP in adjuvant-induced inflamed rats. | 2001 Jan 15 |
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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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Role of corticostriatal and nigrostriatal inputs in malonate-induced striatal toxicity. | 2001 Jan 22 |
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Intranigral transplantation of solid tissue ventral mesencephalon or striatal grafts induces behavioral recovery in 6-OHDA-lesioned rats. | 2001 Jan 26 |
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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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Bcl-2 and GDNF delivered by HSV-mediated gene transfer act additively to protect dopaminergic neurons from 6-OHDA-induced degeneration. | 2001 Jun |
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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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Serotonin, norepinephrine and dopamine involvement in the antidepressant action of hypericum perforatum. | 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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Selective dopamine receptor stimulation differentially affects [3H]arachidonic acid incorporation, a surrogate marker for phospholipase A2-mediated neurotransmitter signal transduction, in a rodent model 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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Modulation of visceral nociceptive responses of rat spinal dorsal horn neurons by sympathectomy. | 2001 Mar 26 |
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Neuroprotective effects of GDNF against 6-OHDA in young and aged rats. | 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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Sustained extracellular signal-regulated kinase activation by 6-hydroxydopamine: implications for Parkinson's disease. | 2001 May |
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Neuroimmunophilin ligands exert neuroregeneration and neuroprotection in midbrain dopaminergic neurons. | 2001 May |
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Evidence for a direct action of Tityus serrulatus scorpion venom on the cardiac muscle. | 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 |
|
Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine. | 2001 May 25 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23758882
Rats were unilaterally lesioned with intrastriatal injections of 8 or 2 × 10 ug Oxidopamine.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24341565
SH-SY5Y cell damage was induced by 150 uM Oxidopamine (6-OHDA), and the cells' viability was examined by MTT assay.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:56:39 GMT 2025
by
admin
on
Mon Mar 31 18:56:39 GMT 2025
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Record UNII |
8HW4YBZ748
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Record Status |
Validated (UNII)
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Record Version |
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Preferred Name | English | ||
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Systematic Name | English |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66883
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4624
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OXIDOPAMINE
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DTXSID0036768
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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
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Related Record | Type | Details | ||
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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 |