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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
Structure of OXIDOPAMINE

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

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

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
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
Regulation of EphB1 expression by dopamine signaling.
2000 Dec 28
Embryonic ventral mesencephalic grafts improve levodopa-induced dyskinesia in a rat model of Parkinson's disease.
2000 Jul
Effects of ropinirole on various parkinsonian models in mice, rats, and cynomolgus monkeys.
2000 Mar
Delivery of a GDNF gene into the substantia nigra after a progressive 6-OHDA lesion maintains functional nigrostriatal connections.
2000 Nov
Enhanced axonal growth from fetal human bcl-2 transgenic mouse dopamine neurons transplanted to the adult rat striatum.
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
Septal cholinergic neurons suppress seizure development in hippocampal kindling in rats: comparison with noradrenergic neurons.
2001
Alterations in cortical and basal ganglia levels of opioid receptor binding in a rat model of l-DOPA-induced dyskinesia.
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
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
Differential expression of GDNF, BDNF, and NT-3 in the aging nigrostriatal system following a neurotoxic lesion.
2001 Feb 9
High frequency stimulation of the subthalamic nucleus increases the extracellular contents of striatal dopamine in normal and partially dopaminergic denervated rats.
2001 Jan
Melatonin protects against 6-OHDA-induced neurotoxicity in rats: a role for mitochondrial complex I activity.
2001 Jan
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
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
Regulation of GAP-43 protein and mRNA in nigrostriatal dopaminergic neurons after the partial destruction of dopaminergic terminals with intrastriatal 6-hydroxydopamine.
2001 Jan
The small molecule FKBP ligand GPI 1046 induces partial striatal re-innervation after intranigral 6-hydroxydopamine lesion in rats.
2001 Jan 12
Alteration of spontaneous firing rate of primary myelinated afferents by ATP in adjuvant-induced inflamed rats.
2001 Jan 15
Fetal intra-nigral ventral mesencephalon and kidney tissue bridge transplantation restores the nigrostriatal dopamine pathway in hemi-parkinsonian rats.
2001 Jan 19
Role of corticostriatal and nigrostriatal inputs in malonate-induced striatal toxicity.
2001 Jan 22
Intranigral transplantation of solid tissue ventral mesencephalon or striatal grafts induces behavioral recovery in 6-OHDA-lesioned rats.
2001 Jan 26
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
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
Immunophilin ligands can prevent progressive dopaminergic degeneration in animal models of Parkinson's disease.
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
6-hydroxydopamine-induced lesions of dopaminergic neurons alter the function of postsynaptic cholinergic neurons without changing cytoskeletal proteins.
2001 Mar
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
Evidence for a direct action of Tityus serrulatus scorpion venom on the cardiac muscle.
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
Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine.
2001 May 25
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 18:56:39 GMT 2025
Edited
by admin
on Mon Mar 31 18:56:39 GMT 2025
Record UNII
8HW4YBZ748
Record Status Validated (UNII)
Record Version
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Name Type Language
OXIDOPAMINE [USAN]
Preferred Name English
OXIDOPAMINE
INN   USAN  
INN   USAN  
Official 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 Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
Code System Code Type Description
PUBCHEM
4624
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
WIKIPEDIA
OXIDOPAMINE
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
EPA CompTox
DTXSID0036768
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
NCI_THESAURUS
C1316
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
INN
4232
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
EVMPD
SUB09524MIG
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
SMS_ID
100000083061
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
FDA UNII
8HW4YBZ748
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
CHEBI
78741
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
ChEMBL
CHEMBL337702
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
CAS
1199-18-4
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
MESH
D016627
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
ECHA (EC/EINECS)
214-842-3
Created by admin on Mon Mar 31 18:56:39 GMT 2025 , Edited by admin on Mon Mar 31 18:56:39 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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PARENT -> METABOLITE TOXIC
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ACTIVE MOIETY