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
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
| 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 |
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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Enhanced axonal growth from fetal human bcl-2 transgenic mouse dopamine neurons transplanted to the adult rat striatum. | 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 |
|
| 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 |
|
| 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 |
|
| Effect of 6-hydroxydopamine or repeated amphetamine treatment on mesencephalic mRNA levels for AMPA glutamate receptor subunits in the rat. | 2001 Apr 20 |
|
| 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 |
|
| 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 |
|
| Norepinephrine modulates myelopoiesis after experimental thermal injury with sepsis. | 2001 Feb |
|
| Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
|
| Dinapsoline: characterization of a D1 dopamine receptor agonist in a rat model of Parkinson's disease. | 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 |
|
| Ingrowth of sympathetic innervation occurs concomitantly with a decrease of ANP in the growing rat cardiac ventricles. | 2001 Jan |
|
| Influence of time in culture and BDNF pretreatment on survival and function of grafted embryonic rat ventral mesencephalon in the 6-OHDA rat model of Parkinson's disease. | 2001 Jan |
|
| Simultaneous intrastriatal 6-hydroxydopamine and quinolinic acid injection: a model of early-stage striatonigral degeneration. | 2001 Jan |
|
| 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 |
|
| 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 |
|
| 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 |
|
| The pasta matrix reaching task: a simple test for measuring skilled reaching distance, direction, and dexterity in 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 |
|
| Glial cell line-derived neurotrophic factor (GDNF) gene delivery protects dopaminergic terminals from degeneration. | 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 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:21:56 GMT 2025
by
admin
on
Mon Mar 31 19:21:56 GMT 2025
|
| Record UNII |
9WBV30HXTL
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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160157
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28094-15-7
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9WBV30HXTL
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DTXSID0045838
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233898
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248-837-2
Created by
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