OXIDOPAMINE

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 Search

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

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
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	10600402
Regulation of EphB1 expression by dopamine signaling.	2000 Dec 28	11146119
Embryonic ventral mesencephalic grafts improve levodopa-induced dyskinesia in a rat model of Parkinson's disease.	2000 Jul	10869049
Effects of ropinirole on various parkinsonian models in mice, rats, and cynomolgus monkeys.	2000 Mar	10683491
Delivery of a GDNF gene into the substantia nigra after a progressive 6-OHDA lesion maintains functional nigrostriatal connections.	2000 Nov	11031079
Enhanced axonal growth from fetal human bcl-2 transgenic mouse dopamine neurons transplanted to the adult rat striatum.	2001	11377843
Unilateral dopamine depletion increases expression of the 2A subunit of the N-methyl-D-aspartate receptor in enkephalin-positive and enkephalin-negative neurons.	2001	11246155
Septal cholinergic neurons suppress seizure development in hippocampal kindling in rats: comparison with noradrenergic neurons.	2001	11182245
Alterations in cortical and basal ganglia levels of opioid receptor binding in a rat model of l-DOPA-induced dyskinesia.	2001 Apr	11300719
A nitric oxide-dopamine link pathway in organum vasculosum laminae terminalis of rat brain exerts control over blood pressure.	2001 Apr	11264246
Retrograde tracing techniques influence reported death rates of adult rat nigrostriatal neurons.	2001 Apr	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 Apr	11259111
Lesion of the bulbospinal noradrenergic pathways blocks desipramine-induced inhibition of the C-fiber evoked nociceptive reflex in rats.	2001 Apr 13	11278097
Circadian rhythm of drinking and running-wheel activity in rats with 6-hydroxydopamine lesions of the ventral tegmental area.	2001 Apr 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 Apr 27	11311875
Differential expression of GDNF, BDNF, and NT-3 in the aging nigrostriatal system following a neurotoxic lesion.	2001 Feb 9	11164827
High frequency stimulation of the subthalamic nucleus increases the extracellular contents of striatal dopamine in normal and partially dopaminergic denervated rats.	2001 Jan	11202172
Melatonin protects against 6-OHDA-induced neurotoxicity in rats: a role for mitochondrial complex I activity.	2001 Jan	11149904
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	11135014
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	11134999
Regulation of GAP-43 protein and mRNA in nigrostriatal dopaminergic neurons after the partial destruction of dopaminergic terminals with intrastriatal 6-hydroxydopamine.	2001 Jan	11071705
The small molecule FKBP ligand GPI 1046 induces partial striatal re-innervation after intranigral 6-hydroxydopamine lesion in rats.	2001 Jan 12	11121883
Alteration of spontaneous firing rate of primary myelinated afferents by ATP in adjuvant-induced inflamed rats.	2001 Jan 15	11275402
Fetal intra-nigral ventral mesencephalon and kidney tissue bridge transplantation restores the nigrostriatal dopamine pathway in hemi-parkinsonian rats.	2001 Jan 19	11166704
Role of corticostriatal and nigrostriatal inputs in malonate-induced striatal toxicity.	2001 Jan 22	11201098
Intranigral transplantation of solid tissue ventral mesencephalon or striatal grafts induces behavioral recovery in 6-OHDA-lesioned rats.	2001 Jan 26	11164771
Motor behavioural changes after intracerebroventricular injection of 6-hydroxydopamine in the rat: an animal model of Parkinson's disease.	2001 Jul	11287079
Bcl-2 and GDNF delivered by HSV-mediated gene transfer act additively to protect dopaminergic neurons from 6-OHDA-induced degeneration.	2001 Jun	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 Jun	11331148
Entopeduncular lesions facilitate and thalamic lesions depress spontaneous and drug-evoked motor behavior in the hemiparkinsonian rat.	2001 Jun 1	11304759
Serotonin, norepinephrine and dopamine involvement in the antidepressant action of hypericum perforatum.	2001 Mar	11302563
Immunophilin ligands can prevent progressive dopaminergic degeneration in animal models of Parkinson's disease.	2001 Mar	11285005
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	11181943
6-hydroxydopamine-induced lesions of dopaminergic neurons alter the function of postsynaptic cholinergic neurons without changing cytoskeletal proteins.	2001 Mar	11170728
Modulation of visceral nociceptive responses of rat spinal dorsal horn neurons by sympathectomy.	2001 Mar 26	11277586
Neuroprotective effects of GDNF against 6-OHDA in young and aged rats.	2001 Mar 30	11277973
Disruption of dopaminergic neurotransmission in nucleus accumbens core inhibits the locomotor stimulant effects of nicotine and D-amphetamine in rats.	2001 May	11369033
Protective effects of 1 alpha,25-(OH)(2)D(3) against the neurotoxicity of glutamate and reactive oxygen species in mesencephalic culture.	2001 May	11369030
Sustained extracellular signal-regulated kinase activation by 6-hydroxydopamine: implications for Parkinson's disease.	2001 May	11359871
Neuroimmunophilin ligands exert neuroregeneration and neuroprotection in midbrain dopaminergic neurons.	2001 May	11359520
Evidence for a direct action of Tityus serrulatus scorpion venom on the cardiac muscle.	2001 May	11072050
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	11370668
Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine.	2001 May 25	11376600

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 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

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