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

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

CAS No.:
161832-65-1
Catalog Number:
AG007F0V
Molecular Formula:
C19H19N3O3
Molecular Weight:
337.3725
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%
1 week
United States
$190
- +
10mg
98%
1 week
United States
$257
- +
25mg
≥98%
1 week
United States
$607
- +
50mg
98%
1 week
United States
$740
- +
100mg
98%
1 week
United States
$1157
- +
Product Description
Catalog Number:
AG007F0V
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
IUPAC Name:
1-[(8R)-5-(4-aminophenyl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-7-yl]ethanone
InChI:
InChI=1S/C19H19N3O3/c1-11-7-14-8-17-18(25-10-24-17)9-16(14)19(21-22(11)12(2)23)13-3-5-15(20)6-4-13/h3-6,8-9,11H,7,10,20H2,1-2H3/t11-/m1/s1
InChI Key:
JACAAXNEHGBPOQ-LLVKDONJSA-N
SMILES:
Nc1ccc(cc1)C1=NN(C(=O)C)[C@@H](Cc2c1cc1OCOc1c2)C
UNII:
CVS43XG1L5
NSC Number:
729898
Properties
Complexity:
544  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
337.143g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
337.379g/mol
Monoisotopic Mass:
337.143g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
77.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.7  
Literature
Title Journal
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Talampanel reduces the level of motoneuronal calcium in transgenic mutant SOD1 mice only if applied presymptomatically. Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20110901
Glutamate and the biology of gliomas. Glia 20110801
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A phase II trial of talampanel in subjects with amyotrophic lateral sclerosis. Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20100503
Survival of patients with newly diagnosed glioblastoma treated with radiation and temozolomide in research studies in the United States. Clinical cancer research : an official journal of the American Association for Cancer Research 20100415
Phase 2 trial of talampanel, a glutamate receptor inhibitor, for adults with recurrent malignant gliomas. Cancer 20100401
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Talampanel suppresses the acute and chronic effects of seizures in a rodent neonatal seizure model. Epilepsia 20090401
Early alterations of AMPA receptors mediate synaptic potentiation induced by neonatal seizures. The Journal of neuroscience : the official journal of the Society for Neuroscience 20080806
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. Bioorganic & medicinal chemistry 20080301
Neuroprotective and anticonvulsant effects of EGIS-8332, a non-competitive AMPA receptor antagonist, in a range of animal models. British journal of pharmacology 20070901
Effects of 2,3-benzodiazepine AMPA receptor antagonists on dopamine turnover in the striatum of rats with experimental parkinsonism. Brain research bulletin 20070315
[A new aspect in the research on antiepileptic drugs]. Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20070201
Talampanel. Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics 20070101
Novel potent anticonvulsant agent containing a tetrahydroisoquinoline skeleton. Journal of medicinal chemistry 20060907
Talampanel a non-competitive AMPA-antagonist attenuates caspase-3 dependent apoptosis in mouse brain after transient focal cerebral ischemia. Brain research bulletin 20060731
3D pharmacophore models for 1,2,3,4-tetrahydroisoquinoline derivatives acting as anticonvulsant agents. Archiv der Pharmazie 20060701
Influence of the N-acetylation polymorphism on the metabolism of talampanel: an investigation in fasted and fed subjects genotyped for NAT2 variants. Die Pharmazie 20060201
Talampanel improves the functional deficit after transient focal cerebral ischemia in rats. A 30-day follow up study. Brain research bulletin 20060115
Potential metabolites of a condensed 2,3-benzodiazepine derivative. Bioorganic & medicinal chemistry letters 20051101
The effects of AMPA receptor antagonists in models of stroke and neurodegeneration. European journal of pharmacology 20050905
New features in synthesis of talampanel related 2,3-benzodiazepines. Medicinal chemistry (Shariqah (United Arab Emirates)) 20050901
Unified pharmacogenetics-based parent-metabolite pharmacokinetic model incorporating acetylation polymorphism for talampanel in humans. Journal of pharmacokinetics and pharmacodynamics 20050801
The AMPA-antagonist talampanel is neuroprotective in rodent models of focal cerebral ischemia. Brain research bulletin 20050715
Influence of the combined treatment of LY 300164 (an AMPA/kainate receptor antagonist) with adenosine receptor agonists on the electroconvulsive threshold in mice. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20041001
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. Brain research 20040522
Omeprazole and talampanel as two examples of retrometabolic drug design. Die Pharmazie 20040501
Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives. Farmaco (Societa chimica italiana : 1989) 20040101
AMPA receptor blockade potentiates the stimulatory effect of L-DOPA on dopamine release in dopamine-deficient corticostriatal slice preparation. Critical reviews in neurobiology 20040101
Is a hypothermic effect of LY300164, valproate and phenobarbital evident in mice? Roczniki Akademii Medycznej w Bialymstoku (1995) 20040101
Influence of LY 300164 alone or in combination with carbamazepine or diphenylhydantoin on the body temperature in mice. Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20040101
Synthesis and evaluation of pharmacological properties of novel annelated 2,3-benzodiazepine derivatives. Journal of medicinal chemistry 20030814
Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist. Journal of medicinal chemistry 20030102
Talampanel, a new antiepileptic drug: single- and multiple-dose pharmacokinetics and initial 1-week experience in patients with chronic intractable epilepsy. Epilepsia 20030101
Influence of LY 300164, an AMPA/kainate receptor antagonist upon the anticonvulsant action of antiepileptic drugs against aminophylline-induced seizures in mice. Polish journal of pharmacology 20030101
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 of physiology and pharmacology : an official journal of the Polish Physiological Society 20021201
Protective effect of the antiepileptic drug candidate talampanel against AMPA-induced striatal neurotoxicity in neonatal rats. Brain research bulletin 20021015
Influence of agents affecting voltage-dependent calcium channels and dantrolene on the anticonvulsant action of the AMPA/kainate receptor antagonist LY 300164 in mice. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20020801
Na(+) entry through AMPA receptors results in voltage-gated k(+) channel blockade in cultured rat spinal cord motoneurons. Journal of neurophysiology 20020801
A crossover, add-on trial of talampanel in patients with refractory partial seizures. Neurology 20020611
AMPA and GABA(B) receptor antagonists and their interaction in rats with a genetic form of absence epilepsy. European journal of pharmacology 20011102
Talampanel, a novel noncompetitive AMPA antagonist, is neuroprotective after traumatic brain injury in rats. Journal of neurotrauma 20011001
Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655. Brain research bulletin 20010601
A kainate receptor increases the efficacy of GABAergic synapses. Neuron 20010501
AMPA receptor blockade improves levodopa-induced dyskinesia in MPTP monkeys. Neurology 20000425
Influence of LY 300164, an antagonist of AMPA/kainate receptors, on the anticonvulsant activity of clonazepam. European journal of pharmacology 19990910
Properties