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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
Structure of OXIDOPAMINE HYDROBROMIDE

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
12.0 nM [Ki]
51.0 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
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

Rats were unilaterally lesioned with intrastriatal injections of 8 or 2 × 10 ug Oxidopamine.
Route of Administration: Other
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 Mon Mar 31 17:51:34 GMT 2025
Edited
by admin
on Mon Mar 31 17:51:34 GMT 2025
Record UNII
TWC1D4W0WB
Record Status Validated (UNII)
Record Version
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Name Type Language
NSC-238469
Preferred Name English
OXIDOPAMINE HYDROBROMIDE
Common Name English
6-HYDROXYDOPAMINE HYDROBROMIDE
Systematic Name English
1,2,4-BENZENETRIOL, 5-(2-AMINOETHYL)-, HYDROBROMIDE (1:1)
Systematic Name English
1,2,4-BENZENETRIOL, 5-(2-AMINOETHYL)-, HYDROBROMIDE
Systematic Name English
2-(2,4,5-TRIHYDROXYPHENYL)ETHYLAMINE HYDROBROMIDE
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
211-247-0
Created by admin on Mon Mar 31 17:51:34 GMT 2025 , Edited by admin on Mon Mar 31 17:51:34 GMT 2025
PRIMARY
PUBCHEM
176170
Created by admin on Mon Mar 31 17:51:34 GMT 2025 , Edited by admin on Mon Mar 31 17:51:34 GMT 2025
PRIMARY
EPA CompTox
DTXSID30212972
Created by admin on Mon Mar 31 17:51:34 GMT 2025 , Edited by admin on Mon Mar 31 17:51:34 GMT 2025
PRIMARY
CAS
636-00-0
Created by admin on Mon Mar 31 17:51:34 GMT 2025 , Edited by admin on Mon Mar 31 17:51:34 GMT 2025
PRIMARY
NSC
238469
Created by admin on Mon Mar 31 17:51:34 GMT 2025 , Edited by admin on Mon Mar 31 17:51:34 GMT 2025
PRIMARY
FDA UNII
TWC1D4W0WB
Created by admin on Mon Mar 31 17:51:34 GMT 2025 , Edited by admin on Mon Mar 31 17:51:34 GMT 2025
PRIMARY
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