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76778-22-8,MFCD00600387
Catalog No.:AA008PAN

76778-22-8 | GBR 12935

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1g
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA008PAN
Chemical Name:
GBR 12935
CAS Number:
76778-22-8
Molecular Formula:
C32H38N2O5
Molecular Weight:
530.6545
MDL Number:
MFCD00600387
SMILES:
c1ccc(cc1)CCCN1CCN(CC1)CCOC(c1ccccc1)c1ccccc1.OC(=O)/C=C\C(=O)O
Properties
Computed Properties
 
Complexity:
440  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
3  
Rotatable Bond Count:
10  
XLogP3:
5.4  

Literature

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Title: Time-dependent changes in GLT-1 functioning in striatum of hemi-Parkinson rats.

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Title: The effect of chronic methylphenidate administration on presynaptic dopaminergic parameters in a rat model for ADHD.

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Title: HPC-1/syntaxin 1A gene knockout mice show abnormal behavior possibly related to a disruption in 5-HTergic systems.

Journal: The European journal of neuroscience 20100701

Title: Improved tricyclic inhibitors of trypanothione reductase by screening and chemical synthesis.

Journal: ChemMedChem 20090803

Title: HIV-1 Tat protein-induced rapid and reversible decrease in [3H]dopamine uptake: dissociation of [3H]dopamine uptake and [3H]2beta-carbomethoxy-3-beta-(4-fluorophenyl)tropane (WIN 35,428) binding in rat striatal synaptosomes.

Journal: The Journal of pharmacology and experimental therapeutics 20090601

Title: Ethanol facilitates glutamatergic transmission to dopamine neurons in the ventral tegmental area.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20090101

Title: Mitochondrial complex I inhibitor rotenone inhibits and redistributes vesicular monoamine transporter 2 via nitration in human dopaminergic SH-SY5Y cells.

Journal: Molecular pharmacology 20081001

Title: Design and synthesis of 2- and 3-substituted-3-phenylpropyl analogs of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine: role of amino, fluoro, hydroxyl, methoxyl, methyl, methylene, and oxo substituents on affinity for the dopamine and serotonin transporters.

Journal: Journal of medicinal chemistry 20080508

Title: Nanomolar propofol stimulates glutamate transmission to dopamine neurons: a possible mechanism of abuse potential?

Journal: The Journal of pharmacology and experimental therapeutics 20080401

Title: Pharmacological characterization and anatomical distribution of the dopamine transporter in the mouse cerebellum.

Journal: Cerebellum (London, England) 20080101

Title: Mitochondrial complex I inhibitor rotenone-elicited dopamine redistribution from vesicles to cytosol in human dopaminergic SH-SY5Y cells.

Journal: The Journal of pharmacology and experimental therapeutics 20071101

Title: Toxic influence of subchronic paraquat administration on dopaminergic neurons in rats.

Journal: Brain research 20070625

Title: Nicotine increases dopamine transporter function in rat striatum through a trafficking-independent mechanism.

Journal: European journal of pharmacology 20070112

Title: Transglutaminase 2 ablation leads to defective function of mitochondrial respiratory complex I affecting neuronal vulnerability in experimental models of extrapyramidal disorders.

Journal: Journal of neurochemistry 20070101

Title: Metabolism of dopamine by the nasal mucosa.

Journal: Journal of pharmaceutical sciences 20061101

Title: Quantitative autoradiography of ligands for dopamine receptors and transporters in brain of Göttingen minipig: comparison with results in vivo.

Journal: Synapse (New York, N.Y.) 20060315

Title: Dopamine transporter blockade increases LTP in the CA1 region of the rat hippocampus via activation of the D3 dopamine receptor.

Journal: Learning & memory (Cold Spring Harbor, N.Y.) 20060301

Title: Alcohol consumption alters dopamine transporter sites in Wistar-Kyoto rat brain.

Journal: Brain research 20060216

Title: Antidepressant drug induced alterations in binding to central dopamine transporter sites in the Wistar Kyoto rat strain.

Journal: Progress in neuro-psychopharmacology & biological psychiatry 20060101

Title: A slowly developing dysfunction of dopaminergic nigrostriatal neurons induced by long-term paraquat administration in rats: an animal model of preclinical stages of Parkinson's disease?

Journal: The European journal of neuroscience 20050901

Title: Cocaine-induced modulation of long-term potentiation in the CA1 region of rat hippocampus.

Journal: Neuropharmacology 20050801

Title: A role of IL-1 in MPTP-induced changes in striatal dopaminergic and serotoninergic transporter binding: clues from interleukin-1 type I receptor-deficient mice.

Journal: Brain research. Molecular brain research 20050520

Title: Specific in vitro binding of (S,S)-[3H]MeNER to norepinephrine transporters.

Journal: Synapse (New York, N.Y.) 20050501

Title: Influence of paraquat on dopaminergic transporter in the rat brain.

Journal: Pharmacological reports : PR 20050101

Title: Interaction between a hydroxypiperidine analogue of 4-(2-benzhydryloxy-ethyl)-1-(4-fluorobenzyl)piperidine and Aspartate 68 in the human dopamine transporter.

Journal: European journal of pharmacology 20041203

Title: Effect of 1,2,3,4,-tetrahydroisoquinoline administration under conditions of CYP2D inhibition on dopamine metabolism, level of tyrosine hydroxylase protein and the binding of [3H]GBR 12,935 to dopamine transporter in the rat nigrostriatal, dopaminergic system.

Journal: Brain research 20040529

Title: Uptake inhibitors but not substrates induce protease resistance in extracellular loop two of the dopamine transporter.

Journal: Molecular pharmacology 20040301

Title: Aspartate 345 of the dopamine transporter is critical for conformational changes in substrate translocation and cocaine binding.

Journal: The Journal of biological chemistry 20040213

Title: Environmental enrichment enhances sensitization to GBR 12935-induced activity and decreases dopamine transporter function in the medial prefrontal cortex.

Journal: Behavioural brain research 20040105

Title: Time-course of the expression of inflammatory cytokines and matrix metalloproteinases in the striatum and mesencephalon of mice injected with 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, a dopaminergic neurotoxin.

Journal: Neuroscience letters 20031009

Title: Novel diphenylalkyl piperazine derivatives with high affinities for the dopamine transporter.

Journal: Bioorganic & medicinal chemistry 20030901

Title: Identification of dopamine transporter in bovine pineal gland using [3H]GBR 12935.

Journal: Journal of pineal research 20030801

Title: Presynaptic control of striatal dopamine neurotransmission in adult vesicular monoamine transporter 2 (VMAT2) mutant mice.

Journal: Journal of neurochemistry 20030501

Title: Further exploration of 1-[2-[Bis-(4-fluorophenyl)methoxy]ethyl]piperazine (GBR 12909): role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter.

Journal: Bioorganic & medicinal chemistry letters 20030407

Title: High affinity hydroxypiperidine analogues of 4-(2-benzhydryloxyethyl)-1-(4-fluorobenzyl)piperidine for the dopamine transporter: stereospecific interactions in vitro and in vivo.

Journal: Journal of medicinal chemistry 20030327

Title: Chronic inhibition of the norepinephrine transporter in the brain participates in seizure sensitization to cocaine and local anesthetics.

Journal: Brain research 20030221

Title: Withdrawal from repeated cocaine alters dopamine transporter protein turnover in the rat striatum.

Journal: The Journal of pharmacology and experimental therapeutics 20030101

Title: Pharmacological characterization of N,N-dimethyl-2-(2-amino-4-methylphenyl thio)benzylamine as a ligand of the serotonin transporter with high affinity and selectivity.

Journal: The Journal of pharmacology and experimental therapeutics 20030101

Title: Carnosine prevents methamphetamine-induced gliosis but not dopamine terminal loss in rats.

Journal: European journal of pharmacology 20020719

Title: Serotonin uptake into dopamine neurons via dopamine transporters: a compensatory alternative.

Journal: Brain research 20020628

Title: Chronic clozapine, but not haloperidol, treatment affects rat brain vesicular monoamine transporter 2.

Journal: European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20020601

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Development of long-acting dopamine transporter ligands as potential cocaine-abuse therapeutic agents: chiral hydroxyl-containing derivatives of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine.

Journal: Journal of medicinal chemistry 20020314

Title: Pharmacological characterisation of (E)-N-(3-iodoprop-2-enyl)-2beta-carbomethoxy-3beta-(4'-methylphenyl)nortropane (PE2I) binding to the rat neuronal dopamine transporter expressed in COS cells.

Journal: Neurochemistry international 20020201

Title: Expansion of structure-activity studies of piperidine analogues of 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine (GBR 12935) compounds by altering substitutions in the N-benzyl moiety and behavioral pharmacology of selected molecules.

Journal: Journal of medicinal chemistry 20020131

Title: Synthesis and biological evaluation of tropane-like 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909) analogues.

Journal: Journal of medicinal chemistry 20011108

Title: Dendrodendritic inhibition through reversal of dopamine transport.

Journal: Science (New York, N.Y.) 20010928

Title: RTI-76, an irreversible inhibitor of dopamine transporter binding, increases locomotor activity in the rat at high doses.

Journal: Brain research 20010406

Title: Subtle differences in the discriminative stimulus effects of cocaine and GBR-12909.

Journal: Progress in neuro-psychopharmacology & biological psychiatry 20010401

Title: Negative interaction of dopamine D2 receptor antagonists and GBR 12909 and GBR 12935 dopamine uptake inhibitors in the nucleus accumbens.

Journal: European journal of pharmacology 20010223

Title: Dopaminergic activity in transgenic mice underexpressing glucocorticoid receptors: effect of antidepressants.

Journal: Neuroscience 20010101

Title: Early methylphenidate administration to young rats causes a persistent reduction in the density of striatal dopamine transporters.

Journal: Journal of child and adolescent psychopharmacology 20010101

Title: Changes in seizure susceptibility to local anesthetics by repeated administration of cocaine and nomifensine but not GBR12935: possible involvement of noradrenergic system.

Journal: Japanese journal of pharmacology 20000701

Title: Oxygenated analogues of 1-[2-(Diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909) as potential extended-action cocaine-abuse therapeutic agents.

Journal: Journal of medicinal chemistry 19991202

Title: Involvement of caspase-like proteinases in apoptosis of neuronal PC12 cells and primary cultured microglia induced by 6-hydroxydopamine.

Journal: Journal of neuroscience research 19981015

Title: Effects of benztropine on behavioral and toxic effects of cocaine: comparison with atropine and the selective dopamine uptake inhibitor 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenyl-propyl)-piperazine.

Journal: The Journal of pharmacology and experimental therapeutics 19960401

Title: Pharmacological heterogeneity of the cloned and native human dopamine transporter: disassociation of [3H]WIN 35,428 and [3H]GBR 12,935 binding.

Journal: Molecular pharmacology 19940101

Title: [Effects of antagonists of NMDA receptor on methamphetamine-induced decrease in the dopamine uptake sites in the rat striatum and on the behavioral sensitization].

Journal: [Hokkaido igaku zasshi] The Hokkaido journal of medical science 19930501

Title: Hiroi T, et al. Specific binding of 1--(diphenylmethoxy)ethyl-4-(3-phenyl propyl) piperazine (GBR-12935), an inhibitor of the dopamine transporter, to human CYP2D6. Biochem Pharmacol. 1997 Jun 15;53(12):1937-9.

Title: Rahman S, et al. Negative interaction of dopamine D2 receptor antagonists and GBR 12909 and GBR 12935 dopamine uptake inhibitors in the nucleus accumbens. Eur J Pharmacol. 2001 Feb 23;414(1):37-44.

Title: Tolliver BK, et al. Comparison of cocaine and GBR 12935: effects on locomotor activity and stereotypy in two inbred mouse strains. Pharmacol Biochem Behav. 1994 Jul;48(3):733-9.

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