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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
Structure of OXIDOPAMINE

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
12 nM [Ki]
51 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
[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
Delayed infusion of GDNF promotes recovery of motor function in the partial lesion model of Parkinson's disease.
2001 Apr
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
Retrograde tracing techniques influence reported death rates of adult rat nigrostriatal neurons.
2001 Apr
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
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
Circadian rhythm of drinking and running-wheel activity in rats with 6-hydroxydopamine lesions of the ventral tegmental area.
2001 Apr 27
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
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
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
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

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 Sat Jun 26 14:16:23 UTC 2021
Edited
by admin
on Sat Jun 26 14:16:23 UTC 2021
Record UNII
8HW4YBZ748
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXIDOPAMINE
INN   USAN  
INN   USAN  
Official Name English
OXIDOPAMINE [USAN]
Common Name English
2,4,5-TRIHYDROXYPHENETHYLAMINE
Systematic Name English
OXIDOPAMINE [INN]
Common Name English
6-HYDROXYDOPAMINE
Systematic Name English
5-(2-AMINOETHYL)BENZENE-1,2,4-TRIOL
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
Code System Code Type Description
PUBCHEM
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
PRIMARY
WIKIPEDIA
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
PRIMARY
EPA CompTox
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
PRIMARY
NCI_THESAURUS
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
PRIMARY
INN
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
PRIMARY
EVMPD
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
PRIMARY
FDA UNII
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
PRIMARY
ChEMBL
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
PRIMARY
CAS
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
PRIMARY
MESH
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
PRIMARY
ECHA (EC/EINECS)
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
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE TOXIC
Related Record Type Details
ACTIVE MOIETY