Home Amines 161832-65-1
161832-65-1,MFCD00871406
Catalog No.:AA007EY3

161832-65-1 | 7H-1,3-Dioxolo[4,5-h][2,3]benzodiazepine,7-acetyl-5-(4-aminophenyl)-8,9-dihydro-8-methyl-, (8R)-

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5mg
≥98%
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10mg
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$210.00   $147.00
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25mg
≥98%
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$350.00   $245.00
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50mg
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500mg
98% by HPLC
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1000mg
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  • Technical Information
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA007EY3
Chemical Name:
7H-1,3-Dioxolo[4,5-h][2,3]benzodiazepine,7-acetyl-5-(4-aminophenyl)-8,9-dihydro-8-methyl-, (8R)-
CAS Number:
161832-65-1
Molecular Formula:
C19H19N3O3
Molecular Weight:
337.3725
MDL Number:
MFCD00871406
SMILES:
Nc1ccc(cc1)C1=NN(C(=O)C)[C@@H](Cc2c1cc1OCOc1c2)C
NSC Number:
729898
Properties
Computed Properties
 
Complexity:
544  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
1  
XLogP3:
2.7  

Literature

Title: Mechanism of inhibition of the GluA2 AMPA receptor channel opening by talampanel and its enantiomer: the stereochemistry of the 4-methyl group on the diazepine ring of 2,3-benzodiazepine derivatives.

Journal: ACS chemical neuroscience 20130417

Title: Talampanel reduces the level of motoneuronal calcium in transgenic mutant SOD1 mice only if applied presymptomatically.

Journal: Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20110901

Title: Glutamate and the biology of gliomas.

Journal: Glia 20110801

Title: alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) antagonists: from bench to bedside.

Journal: Journal of medicinal chemistry 20100812

Title: A phase II trial of talampanel in subjects with amyotrophic lateral sclerosis.

Journal: Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20100503

Title: Survival of patients with newly diagnosed glioblastoma treated with radiation and temozolomide in research studies in the United States.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20100415

Title: Phase 2 trial of talampanel, a glutamate receptor inhibitor, for adults with recurrent malignant gliomas.

Journal: Cancer 20100401

Title: Talampanel with standard radiation and temozolomide in patients with newly diagnosed glioblastoma: a multicenter phase II trial.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20090901

Title: [New roles of glutamate receptors in glias and gliomas].

Journal: Brain and nerve = Shinkei kenkyu no shinpo 20090701

Title: Talampanel suppresses the acute and chronic effects of seizures in a rodent neonatal seizure model.

Journal: Epilepsia 20090401

Title: Early alterations of AMPA receptors mediate synaptic potentiation induced by neonatal seizures.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20080806

Title: Structure-activity study of 2,3-benzodiazepin-4-ones noncompetitive AMPAR antagonists: identification of the 1-(4-amino-3-methylphenyl)-3,5-dihydro-7,8-ethylenedioxy-4H-2,3-benzodiazepin-4-one as neuroprotective agent.

Journal: Bioorganic & medicinal chemistry 20080301

Title: Neuroprotective and anticonvulsant effects of EGIS-8332, a non-competitive AMPA receptor antagonist, in a range of animal models.

Journal: British journal of pharmacology 20070901

Title: Effects of 2,3-benzodiazepine AMPA receptor antagonists on dopamine turnover in the striatum of rats with experimental parkinsonism.

Journal: Brain research bulletin 20070315

Title: [A new aspect in the research on antiepileptic drugs].

Journal: Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20070201

Title: Talampanel.

Journal: Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics 20070101

Title: Novel potent anticonvulsant agent containing a tetrahydroisoquinoline skeleton.

Journal: Journal of medicinal chemistry 20060907

Title: Talampanel a non-competitive AMPA-antagonist attenuates caspase-3 dependent apoptosis in mouse brain after transient focal cerebral ischemia.

Journal: Brain research bulletin 20060731

Title: 3D pharmacophore models for 1,2,3,4-tetrahydroisoquinoline derivatives acting as anticonvulsant agents.

Journal: Archiv der Pharmazie 20060701

Title: Influence of the N-acetylation polymorphism on the metabolism of talampanel: an investigation in fasted and fed subjects genotyped for NAT2 variants.

Journal: Die Pharmazie 20060201

Title: Talampanel improves the functional deficit after transient focal cerebral ischemia in rats. A 30-day follow up study.

Journal: Brain research bulletin 20060115

Title: Potential metabolites of a condensed 2,3-benzodiazepine derivative.

Journal: Bioorganic & medicinal chemistry letters 20051101

Title: The effects of AMPA receptor antagonists in models of stroke and neurodegeneration.

Journal: European journal of pharmacology 20050905

Title: New features in synthesis of talampanel related 2,3-benzodiazepines.

Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) 20050901

Title: Unified pharmacogenetics-based parent-metabolite pharmacokinetic model incorporating acetylation polymorphism for talampanel in humans.

Journal: Journal of pharmacokinetics and pharmacodynamics 20050801

Title: The AMPA-antagonist talampanel is neuroprotective in rodent models of focal cerebral ischemia.

Journal: Brain research bulletin 20050715

Title: Influence of the combined treatment of LY 300164 (an AMPA/kainate receptor antagonist) with adenosine receptor agonists on the electroconvulsive threshold in mice.

Journal: European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20041001

Title: Effect of two noncompetitive AMPA receptor antagonists GYKI 52466 and GYKI 53405 on vigilance, behavior and spike-wave discharges in a genetic rat model of absence epilepsy.

Journal: Brain research 20040522

Title: Omeprazole and talampanel as two examples of retrometabolic drug design.

Journal: Die Pharmazie 20040501

Title: Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives.

Journal: Farmaco (Societa chimica italiana : 1989) 20040101

Title: AMPA receptor blockade potentiates the stimulatory effect of L-DOPA on dopamine release in dopamine-deficient corticostriatal slice preparation.

Journal: Critical reviews in neurobiology 20040101

Title: Is a hypothermic effect of LY300164, valproate and phenobarbital evident in mice?

Journal: Roczniki Akademii Medycznej w Bialymstoku (1995) 20040101

Title: Influence of LY 300164 alone or in combination with carbamazepine or diphenylhydantoin on the body temperature in mice.

Journal: Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20040101

Title: Synthesis and evaluation of pharmacological properties of novel annelated 2,3-benzodiazepine derivatives.

Journal: Journal of medicinal chemistry 20030814

Title: Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist.

Journal: Journal of medicinal chemistry 20030102

Title: Talampanel, a new antiepileptic drug: single- and multiple-dose pharmacokinetics and initial 1-week experience in patients with chronic intractable epilepsy.

Journal: Epilepsia 20030101

Title: Influence of LY 300164, an AMPA/kainate receptor antagonist upon the anticonvulsant action of antiepileptic drugs against aminophylline-induced seizures in mice.

Journal: Polish journal of pharmacology 20030101

Title: Influence of several convulsants on the protective activity of a non-competitive AMPA/kainate antagonist, LY 300164, and lamotrigine against maximal electroshock in mice.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20021201

Title: Protective effect of the antiepileptic drug candidate talampanel against AMPA-induced striatal neurotoxicity in neonatal rats.

Journal: Brain research bulletin 20021015

Title: Influence of agents affecting voltage-dependent calcium channels and dantrolene on the anticonvulsant action of the AMPA/kainate receptor antagonist LY 300164 in mice.

Journal: European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20020801

Title: Na(+) entry through AMPA receptors results in voltage-gated k(+) channel blockade in cultured rat spinal cord motoneurons.

Journal: Journal of neurophysiology 20020801

Title: A crossover, add-on trial of talampanel in patients with refractory partial seizures.

Journal: Neurology 20020611

Title: AMPA and GABA(B) receptor antagonists and their interaction in rats with a genetic form of absence epilepsy.

Journal: European journal of pharmacology 20011102

Title: Talampanel, a novel noncompetitive AMPA antagonist, is neuroprotective after traumatic brain injury in rats.

Journal: Journal of neurotrauma 20011001

Title: Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655.

Journal: Brain research bulletin 20010601

Title: A kainate receptor increases the efficacy of GABAergic synapses.

Journal: Neuron 20010501

Title: AMPA receptor blockade improves levodopa-induced dyskinesia in MPTP monkeys.

Journal: Neurology 20000425

Title: Influence of LY 300164, an antagonist of AMPA/kainate receptors, on the anticonvulsant activity of clonazepam.

Journal: European journal of pharmacology 19990910

Title: Paizs M, et al. Talampanel reduces the level of motoneuronal calcium in transgenic mutant SOD1 mice only if applied presymptomatically. Amyotroph Lateral Scler. 2011 Sep;12(5):340-4.

Title: Denes L, et al. Talampanel a non-competitive AMPA-antagonist attenuates caspase-3 dependent apoptosis in mouse brain after transient focal cerebral ischemia. Brain Res Bull. 2006 Jul 31;70(3):260-2. Epub 2006 Mar 31.

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Tags:161832-65-1 Molecular Formula|161832-65-1 MDL|161832-65-1 SMILES|161832-65-1 7H-1,3-Dioxolo[4,5-h][2,3]benzodiazepine,7-acetyl-5-(4-aminophenyl)-8,9-dihydro-8-methyl-, (8R)-