Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H11NO3.BrH |
Molecular Weight | 250.09 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.NCCC1=CC(O)=C(O)C=C1O
InChI
InChIKey=MLACDGUOKDOLGC-UHFFFAOYSA-N
InChI=1S/C8H11NO3.BrH/c9-2-1-5-3-7(11)8(12)4-6(5)10;/h3-4,10-12H,1-2,9H2;1H
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 |
Molecular Formula | BrH |
Molecular Weight | 80.912 |
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 |
---|---|---|---|
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 |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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 |
|
Co-transmitter function of ATP in central catecholaminergic neurons of the rat. | 2001 |
|
Septal cholinergic neurons suppress seizure development in hippocampal kindling in rats: comparison with noradrenergic neurons. | 2001 |
|
[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 |
|
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 |
|
Retrograde tracing techniques influence reported death rates of adult rat nigrostriatal neurons. | 2001 Apr |
|
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 |
|
Circadian rhythm of drinking and running-wheel activity in rats with 6-hydroxydopamine lesions of the ventral tegmental area. | 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 |
|
Dorsal and ventral medullary catecholamine cell groups contribute differentially to systemic interleukin-1beta-induced hypothalamic pituitary adrenal axis responses. | 2001 Feb |
|
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 |
|
Microglial response to the neurotoxicity of 6-hydroxydopamine in neonatal rat cerebellum. | 2001 Feb |
|
Norepinephrine modulates myelopoiesis after experimental thermal injury with sepsis. | 2001 Feb |
|
Neuroprotective effect of vitamin E on the early model of Parkinson's disease in rat: behavioral and histochemical evidence. | 2001 Feb 16 |
|
Molecular mechanism in activation of glutathione system by ropinirole, a selective dopamine D2 agonist. | 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 |
|
Ingrowth of sympathetic innervation occurs concomitantly with a decrease of ANP in the growing rat cardiac ventricles. | 2001 Jan |
|
Protective effect of quinacrine on striatal dopamine levels in 6-OHDA and MPTP models of Parkinsonism in rodents. | 2001 Jan 1 |
|
Alteration of spontaneous firing rate of primary myelinated afferents by ATP in adjuvant-induced inflamed rats. | 2001 Jan 15 |
|
Intranigral transplantation of solid tissue ventral mesencephalon or striatal grafts induces behavioral recovery in 6-OHDA-lesioned rats. | 2001 Jan 26 |
|
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 |
|
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 |
|
Central beta-amyloid peptide-induced peripheral interleukin-6 responses in mice. | 2001 Mar |
|
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 |
|
IGF-I and bFGF improve dopamine neuron survival and behavioral outcome in parkinsonian rats receiving cultured human fetal tissue strands. | 2001 Mar |
|
6-hydroxydopamine-induced lesions of dopaminergic neurons alter the function of postsynaptic cholinergic neurons without changing cytoskeletal proteins. | 2001 Mar |
|
Chemical sympathectomy increases the innate immune response and decreases the specific immune response in the spleen to infection with Listeria monocytogenes. | 2001 Mar 1 |
|
Neuroprotective effects of GDNF against 6-OHDA in young and aged rats. | 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 |
|
Glial cell line-derived neurotrophic factor (GDNF) gene delivery protects dopaminergic terminals from degeneration. | 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
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
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admin
on
Edited
Mon Mar 31 17:51:34 GMT 2025
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on
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Record UNII |
TWC1D4W0WB
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Record Status |
Validated (UNII)
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Record Version |
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176170
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636-00-0
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238469
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TWC1D4W0WB
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