OXIDOPAMINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H11NO3.ClH
Molecular Weight	205.639
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.NCCC1=C(O)C=C(O)C(O)=C1

InChI

InChIKey=QLMRJHFAGVFUAC-UHFFFAOYSA-N

InChI=1S/C8H11NO3.ClH/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	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C1316 | https://www.ncbi.nlm.nih.gov/pubmed/26346882 | https://www.ncbi.nlm.nih.gov/pubmed/1277142

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine transporter 183 Target ID: CHEMBL338 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562944	Interacts 323		12.0 nM [Ki]
Norepinephrine transporter 197 Target ID: CHEMBL304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562944	Interacts 323		51.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Neuroblastoma 26 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8625308 https://www.ncbi.nlm.nih.gov/pubmed/3084496 https://www.ncbi.nlm.nih.gov/pubmed/7037175	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Motor behavioural changes after intracerebroventricular injection of 6-hydroxydopamine in the rat: an animal model of Parkinson's disease.	2001-07	11287079
Generation of dopaminergic neurons in the adult brain from mesencephalic precursor cells labeled with a nestin-GFP transgene.	2001-06-01	11356877
Free 3-nitrotyrosine causes striatal neurodegeneration in vivo.	2001-06-01	11344255
Entopeduncular lesions facilitate and thalamic lesions depress spontaneous and drug-evoked motor behavior in the hemiparkinsonian rat.	2001-06-01	11304759
Bcl-2 and GDNF delivered by HSV-mediated gene transfer act additively to protect dopaminergic neurons from 6-OHDA-induced degeneration.	2001-06	11358438
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.	2001-06	11331148
Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine.	2001-05-25	11376600
Enhancement of sensorimotor behavioral recovery in hemiparkinsonian rats with intrastriatal, intranigral, and intrasubthalamic nucleus dopaminergic transplants.	2001-05-15	11331381
Striatal dopaminergic metabolism is increased by deep brain stimulation of the subthalamic nucleus in 6-hydroxydopamine lesioned rats.	2001-05-11	11323111
6-hydroxydopamine increases hydroxyl free radical production and DNA damage in rat striatum.	2001-05-08	11338183
BDNF controls dopamine D3 receptor expression and triggers behavioural sensitization.	2001-05-03	11333982
Reaction of oxygen with 6-hydroxydopamine catalyzed by Cu, Fe, Mn, and V complexes: identification of a thermodynamic window for effective metal catalysis.	2001-05-01	11370668
Disruption of dopaminergic neurotransmission in nucleus accumbens core inhibits the locomotor stimulant effects of nicotine and D-amphetamine in rats.	2001-05	11369033
Protective effects of 1 alpha,25-(OH)(2)D(3) against the neurotoxicity of glutamate and reactive oxygen species in mesencephalic culture.	2001-05	11369030
Sustained extracellular signal-regulated kinase activation by 6-hydroxydopamine: implications for Parkinson's disease.	2001-05	11359871
Neuroimmunophilin ligands exert neuroregeneration and neuroprotection in midbrain dopaminergic neurons.	2001-05	11359520
Dopamine cell degeneration induced by intraventricular administration of 6-hydroxydopamine in the rat: similarities with cell loss in parkinson's disease.	2001-05	11312569
Coadministration of (-)-OSU6162 with l-DOPA normalizes preproenkephalin mRNA expression in the sensorimotor striatum of primates with unilateral 6-OHDA lesions.	2001-05	11312565
Glial cell line-derived neurotrophic factor (GDNF) gene delivery protects dopaminergic terminals from degeneration.	2001-05	11312561
Diminished survival of mesencephalic dopamine neurons grafted into aged hosts occurs during the immediate postgrafting interval.	2001-05	11312554
Intrasubthalamic injection of 6-hydroxydopamine induces changes in the firing rate and pattern of subthalamic nucleus neurons in the rat.	2001-05	11252026
Circadian rhythm of drinking and running-wheel activity in rats with 6-hydroxydopamine lesions of the ventral tegmental area.	2001-04-27	11311879
Time-course of changes in firing rates and firing patterns of subthalamic nucleus neuronal activity after 6-OHDA-induced dopamine depletion in rats.	2001-04-27	11311875
Ribozyme-mediated inhibition of caspase-3 activity reduces apoptosis induced by 6-hydroxydopamine in PC12 cells.	2001-04-27	11311863
Effect of 6-hydroxydopamine or repeated amphetamine treatment on mesencephalic mRNA levels for AMPA glutamate receptor subunits in the rat.	2001-04-20	11290405
Growth and functional efficacy of intrastriatal nigral transplants depend on the extent of nigrostriatal degeneration.	2001-04-15	11306640
Lesion of the bulbospinal noradrenergic pathways blocks desipramine-induced inhibition of the C-fiber evoked nociceptive reflex in rats.	2001-04-13	11278097
Delta opioid peptide augments functional effects and intrastriatal graft survival of rat fetal ventral mesencephalic cells.	2001-04-11	11294472
NMDA glutamate receptor stimulation is required for the expression of D2 dopamine mediated responses in apomorphine primed 6-hydroxydopamine lesioned rats.	2001-04-06	11282380
[3H]acetycholine release in rat striatal slices is not subject to dopamine heteroreceptor supersensitivity 30 months after 6-hydroxydopamine lesion of the substantia nigra.	2001-04	11330335
Delayed infusion of GDNF promotes recovery of motor function in the partial lesion model of Parkinson's disease.	2001-04	11328352
Subthalamic infusion of an NMDA antagonist prevents basal ganglia metabolic changes and nigral degeneration in a rodent model of Parkinson's disease.	2001-04	11310632
Dose-related neuroprotective effects of chronic nicotine in 6-hydroxydopamine treated rats, and loss of neuroprotection in alpha4 nicotinic receptor subunit knockout mice.	2001-04	11309235
Alterations in cortical and basal ganglia levels of opioid receptor binding in a rat model of l-DOPA-induced dyskinesia.	2001-04	11300719
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.	2001-04	11279282
A nitric oxide-dopamine link pathway in organum vasculosum laminae terminalis of rat brain exerts control over blood pressure.	2001-04	11264246
Retrograde tracing techniques influence reported death rates of adult rat nigrostriatal neurons.	2001-04	11259131
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.	2001-04	11259111
Neuroprotective effects of GDNF against 6-OHDA in young and aged rats.	2001-03-30	11277973
Modulation of visceral nociceptive responses of rat spinal dorsal horn neurons by sympathectomy.	2001-03-26	11277586
Motor stimulant effects of the adenosine A2A receptor antagonist SCH 58261 do not develop tolerance after repeated treatments in 6-hydroxydopamine-lesioned rats.	2001-03-01	11284438
Serotonin, norepinephrine and dopamine involvement in the antidepressant action of hypericum perforatum.	2001-03	11302563
Effect of chemical sympathectomy with 6-hydroxydopamine on osteoclast activity in the gerbilline middle ear bulla.	2001-03	11300276
Immunophilin ligands can prevent progressive dopaminergic degeneration in animal models of Parkinson's disease.	2001-03	11285005
Alteration of spontaneous firing rate of primary myelinated afferents by ATP in adjuvant-induced inflamed rats.	2001-01-15	11275402
Molecular mechanism in activation of glutathione system by ropinirole, a selective dopamine D2 agonist.	2001-01	11358279
Enhanced axonal growth from fetal human bcl-2 transgenic mouse dopamine neurons transplanted to the adult rat striatum.	2001	11377843
Intrapallidal dopamine restores motor deficits induced by 6-hydroxydopamine in the rat.	2001	11314770
Dopaminergic mRNA expression in the intact substantia nigra of unilaterally 6-OHDA-lesioned and grafted rats: an in situ hybridization study.	2001	11314769
Inhibition of 6-hydroxydopamine-induced p53 expression and survival of neuroblastoma cells following interaction with astrocytes.	2001	11311793

Patents

Sample Use Guides

In Vivo Use Guide

Rats were unilaterally lesioned with intrastriatal injections of 8 or 2 × 10 ug Oxidopamine.

Route of Administration: Other

In Vitro Use Guide

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 19:21:56 GMT 2025` Edited by `admin` on `Mon Mar 31 19:21:56 GMT 2025`
Record UNII	9WBV30HXTL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-233898

Preferred Name

English

OXIDOPAMINE HYDROCHLORIDE

Common Name

English

1,2,4-BENZENETRIOL, 5-(2-AMINOETHYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

1,2,4-BENZENETRIOL, 5-(2-AMINOETHYL)-, HYDROCHLORIDE

Systematic Name

English

6-HYDROXYDOPAMINE HYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

PUBCHEM

160157