Home Amines 102771-26-6
102771-26-6,MFCD00885518
Catalog No.:AA00089V

102771-26-6 | Benzenamine, 4-(8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)-

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00089V
Chemical Name:
Benzenamine, 4-(8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)-
CAS Number:
102771-26-6
Molecular Formula:
C17H15N3O2
Molecular Weight:
293.3199
MDL Number:
MFCD00885518
SMILES:
Nc1ccc(cc1)C1=NN=C(Cc2c1cc1OCOc1c2)C
Properties
Computed Properties
 
Complexity:
482  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
1  
XLogP3:
2.3  

Literature

Title: Peripheral ammonia as a mediator of methamphetamine neurotoxicity.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20120919

Title: Cocaine-taking and cocaine-seeking behaviors in rats remain stable after systemic administration of GYKI 52466: a non-competitive AMPA receptor antagonist.

Journal: Neuroscience letters 20120206

Title: Mechanism of inhibition of the GluA2 AMPA receptor channel opening: consequences of adding an N-3 methylcarbamoyl group to the diazepine ring of 2,3-benzodiazepine derivatives.

Journal: Biochemistry 20110823

Title: Peripheral calcium-permeable AMPA receptors regulate chronic inflammatory pain in mice.

Journal: The Journal of clinical investigation 20110401

Title: The role of NMDA and AMPA/Kainate receptors in the consolidation of catalepsy sensitization.

Journal: Behavioural brain research 20110317

Title: Glutamate receptors in laryngeal cancer cells.

Journal: Anticancer research 20110201

Title: Gender specific influence of endogenous glutamate release on stress-induced fear in rats.

Journal: Endocrine regulations 20110101

Title: Antidepressant-like effects of an AMPA receptor potentiator under a chronic mild stress paradigm.

Journal: The international journal of neuropsychopharmacology 20101001

Title: Involvement of non-NMDA receptors in central mediation of chemoreflexes in the shorthorn sculpin, Myoxocephalus scorpius.

Journal: Respiratory physiology & neurobiology 20100731

Title: Postnatal change of GluR5 kainate receptor expression in the substantia gelatinosa neuron of the trigeminal subnucleus caudalis in mice.

Journal: Brain research 20100730

Title: Stimulation of lateral hypothalamic AMPA receptors may induce feeding in rats.

Journal: Brain research 20100730

Title: Selective excitatory actions of DNQX and CNQX in rat thalamic neurons.

Journal: Journal of neurophysiology 20100401

Title: GYKI-52466: a potential therapeutic agent for glutamate-mediated excitotoxic injury in Cerebral Palsy.

Journal: Medical hypotheses 20100301

Title: Treatment of early and late kainic acid-induced status epilepticus with the noncompetitive AMPA receptor antagonist GYKI 52466.

Journal: Epilepsia 20100101

Title: Glutamatergic mechanisms for speed control and network operation in the rodent locomotor CpG.

Journal: Frontiers in neural circuits 20100101

Title: Furthering pharmacological and physiological assessment of the glutamatergic receptors at the Drosophila neuromuscular junction.

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20091101

Title: Effects of GYKI 52466 on early vasospasm in rats.

Journal: Central European neurosurgery 20091101

Title: Regulation of glutamate transport in developing rat oligodendrocytes.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20090617

Title: Modification of ionotropic glutamate receptor-mediated processes in the rat hippocampus following repeated, brief seizures.

Journal: Neuroscience 20090303

Title: Solution-phase parallel synthesis and evaluation of anticonvulsant activity of N-substituted-3,4-dihydroisoquinoline-2(1H)-carboxamides.

Journal: European journal of medicinal chemistry 20090301

Title: GluK2-mediated excitability within the superficial layers of the entorhinal cortex.

Journal: PloS one 20090101

Title: Pharmacological characterization, localization, and regulation of ionotropic glutamate receptors in skate horizontal cells.

Journal: Visual neuroscience 20090101

Title: CNQX and AMPA inhibit electrical synaptic transmission: a potential interaction between electrical and glutamatergic synapses.

Journal: Brain research 20080904

Title: AMPA receptor-dependent H2O2 generation in striatal medium spiny neurons but not dopamine axons: one source of a retrograde signal that can inhibit dopamine release.

Journal: Journal of neurophysiology 20080901

Title: High-frequency organization and synchrony of activity in the purkinje cell layer of the cerebellum.

Journal: Neuron 20080612

Title: Antagonism of AMPA receptors produces anxiolytic-like behavior in rodents: effects of GYKI 52466 and its novel analogues.

Journal: Psychopharmacology 20080601

Title: Synthesis and anticonvulsant evaluation of N-substituted isoquinoline AMPA receptor antagonists.

Journal: Bioorganic & medicinal chemistry 20080301

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: Involvement of AMPA receptors in the antidepressant-like effects of lithium in the mouse tail suspension test and forced swim test.

Journal: Neuropharmacology 20080301

Title: [Involvement of the amygdala on place aversion induced by naloxone in single-dose morphine-treated rats].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20080301

Title: The role of hippocampal GluR1 and GluR2 receptors in manic-like behavior.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20080102

Title: Blockade of AMPA-receptors attenuates 4-aminopyridine seizures, decreases the activation of inhibitory neurons but is ineffective against seizure-related astrocytic swelling.

Journal: Epilepsy research 20080101

Title: Spontaneous release from mossy fiber terminals inhibits Ni2+-sensitive T-type Ca2+ channels of CA3 pyramidal neurons in the rat organotypic hippocampal slice.

Journal: Hippocampus 20080101

Title: Role of spinal cord alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors in complete Freund's adjuvant-induced inflammatory pain.

Journal: Molecular pain 20080101

Title: AMPA antagonists inhibit the extracellular signal regulated kinase pathway and suppress lung cancer growth.

Journal: Cancer biology & therapy 20071201

Title: AMPA receptor antagonists reverse effects of extended habit training on signaled food approach responding in rats.

Journal: Psychopharmacology 20071101

Title: Activation of extrasynaptic NMDA receptors induces a PKC-dependent switch in AMPA receptor subtypes in mouse cerebellar stellate cells.

Journal: The Journal of physiology 20070901

Title: Benzodiazepine-induced hippocampal CA1 neuron alpha-amino-3-hydroxy-5-methylisoxasole-4-propionic acid (AMPA) receptor plasticity linked to severity of withdrawal anxiety: differential role of voltage-gated calcium channels and N-methyl-D-aspartic acid receptors.

Journal: Behavioural pharmacology 20070901

Title: Presynaptic AMPA and kainate receptors increase the size of GABAergic terminals and enhance GABA release.

Journal: Neuropharmacology 20070601

Title: Differential contribution of kainate receptors to excitatory postsynaptic currents in superficial layer neurons of the rat medial entorhinal cortex.

Journal: Neuroscience 20070525

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: Acute effects of AMPA-type glutamate receptor antagonists on intermale social behavior in two mouse lines bidirectionally selected for offensive aggression.

Journal: Pharmacology, biochemistry, and behavior 20070101

Title: Cyclothiazide prolongs low [Mg2+]-induced seizure-like events.

Journal: Journal of neurophysiology 20061201

Title: Novel potent anticonvulsant agent containing a tetrahydroisoquinoline skeleton.

Journal: Journal of medicinal chemistry 20060907

Title: Purine release from spinal cord microglia after elevation of calcium by glutamate.

Journal: Molecular pharmacology 20060901

Title: Food-induced behavioral sensitization, its cross-sensitization to cocaine and morphine, pharmacological blockade, and effect on food intake.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20060705

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

Journal: Archiv der Pharmazie 20060701

Title: Neural overexcitation and implication of NMDA and AMPA receptors in a mouse model of temporal lobe epilepsy implying zinc chelation.

Journal: Epilepsia 20060501

Title: Effect of glutamate receptor antagonists and antirheumatic drugs on proliferation of synoviocytes in vitro.

Journal: European journal of pharmacology 20060327

Title: Methamphetamine-induced spectrin proteolysis in the rat striatum.

Journal: Journal of neurochemistry 20060301

Title: Glutamate stimulates oligodendrocyte progenitor migration mediated via an alphav integrin/myelin proteolipid protein complex.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20060301

Title: Limited regulation of somatodendritic dopamine release by voltage-sensitive Ca channels contrasted with strong regulation of axonal dopamine release.

Journal: Journal of neurochemistry 20060201

Title: Involvement of the AMPA receptor GluR-C subunit in alcohol-seeking behavior and relapse.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20060125

Title: New 7,8-ethylenedioxy-2,3-benzodiazepines as noncompetitive AMPA receptor antagonists.

Journal: Bioorganic & medicinal chemistry letters 20060101

Title: Localization and function of pre- and postsynaptic kainate receptors in the rat globus pallidus.

Journal: The European journal of neuroscience 20060101

Title: C-type natriuretic peptide modulates glutamate receptors on cultured rat retinal amacrine cells.

Journal: Neuroscience 20060101

Title: A comparison of release kinetics and glutamate receptor properties in shaping rod-cone differences in EPSC kinetics in the salamander retina.

Journal: The Journal of physiology 20051215

Title: Activation of c-Jun NH2-terminal kinase 3 is mediated by the GluR6.PSD-95.MLK3 signaling module following cerebral ischemia in rat hippocampus.

Journal: Brain research 20051102

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

Journal: European journal of pharmacology 20050905

Title: Novel alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionate (AMPA) receptor antagonists of 2,3-benzodiazepine type: chemical synthesis, in vitro characterization, and in vivo prevention of acute neurodegeneration.

Journal: Journal of medicinal chemistry 20050714

Title: Effect of glutamate receptor antagonists on place aversion induced by naloxone in single-dose morphine-treated rats.

Journal: British journal of pharmacology 20050701

Title: A method for producing overactive bladder in the rat and investigation of the effects of GABAergic receptor agonists and glutamatergic receptor antagonists on the cystometrogram.

Journal: The Journal of urology 20050501

Title: C-terminal truncation affects kinetic properties of GluR1 receptors.

Journal: Molecular and cellular neurosciences 20050501

Title: Role of NMDA and AMPA glutamate receptors in the induction and the expression of dopamine-mediated sensitization in 6-hydroxydopamine-lesioned rats.

Journal: Synapse (New York, N.Y.) 20050401

Title: Malignant glioma-induced neuronal cell death in an organotypic glioma invasion model. Technical note.

Journal: Journal of neurosurgery 20050401

Title: AMPA/kainate receptor-mediated downregulation of GABAergic synaptic transmission by calcineurin after seizures in the developing rat brain.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050330

Title: Apoptosis-inducing factor is a key factor in neuronal cell death propagated by BAX-dependent and BAX-independent mechanisms.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050209

Title: Glutamate receptor antagonists and benzodiazepine inhibit the progression of granule cell dispersion in a mouse model of mesial temporal lobe epilepsy.

Journal: Epilepsia 20050201

Title: p21(WAF1/Cip1) is not involved in kainic acid-induced apoptosis in murine cerebellar granule cells.

Journal: Brain research 20041231

Title: Excitotoxic and post-ischemic neurodegeneration: Involvement of transglutaminases.

Journal: Amino acids 20041201

Title: Transient Ca2+-permeable AMPA receptors in postnatal rat primary auditory neurons.

Journal: The European journal of neuroscience 20041201

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: Synthesis and anticonvulsant activity of N-3 substituted 2,3-benzodiazepines.

Journal: Farmaco (Societa chimica italiana : 1989) 20040501

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

Journal: Die Pharmazie 20040501

Title: Immunocytochemical localization and expression of heme oxygenase-1 in primary astroglial cell cultures during differentiation: effect of glutamate.

Journal: Biochemical and biophysical research communications 20040305

Title: Activation of ionotropic glutamate receptors on peripheral axons of primary motoneurons mediates transmitter release at the zebrafish NMJ.

Journal: Journal of neurophysiology 20040201

Title: Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives.

Journal: Farmaco (Societa chimica italiana : 1989) 20040101

Title: Neurotransmitter actions on transient amacrine and ganglion cells of the turtle retina.

Journal: Visual neuroscience 20040101

Title: Glutamate receptor subtypes in human retinal horizontal cells.

Journal: Visual neuroscience 20040101

Title: Administration of a non-NMDA antagonist, GYKI 52466, increases excitotoxic Purkinje cell degeneration caused by ibogaine.

Journal: Neuroscience 20040101

Title: Dopamine D1 receptors mediate CREB phosphorylation via phosphorylation of the NMDA receptor at Ser897-NR1.

Journal: Journal of neurochemistry 20031101

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

Journal: Journal of medicinal chemistry 20030814

Title: Characterization of spontaneous synaptic transmission in rat medial vestibular nucleus.

Journal: Neuroreport 20030806

Title: Glutamate-induced increases in transglutaminase activity in primary cultures of astroglial cells.

Journal: Brain research 20030718

Title: Effect of glutamate receptor antagonists on suckling-induced prolactin release in rats.

Journal: Endocrine 20030701

Title: Participation of AMPA- and NMDA-type excitatory amino acid receptors in the spinal reflex transmission, in rat.

Journal: Brain research bulletin 20030415

Title: AMPA receptors on developing medial septum/diagonal band neurons are sensitive to early postnatal binge-like ethanol exposure.

Journal: Brain research. Developmental brain research 20030414

Title: Glutamate-dependent inhibition of dopamine release in striatum is mediated by a new diffusible messenger, H2O2.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20030401

Title: Neuroprotective effects of GYKI 52466 on experimental spinal cord injury in rats.

Journal: Journal of neurosurgery 20030401

Title: Characterization of the mechanism of anticonvulsant activity for a selected set of putative AMPA receptor antagonists.

Journal: Bioorganic & medicinal chemistry letters 20030210

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

Journal: Journal of medicinal chemistry 20030102

Title: The mitochondrial complex I inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism.

Journal: Neuroscience 20030101

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

Journal: Brain research bulletin 20021015

Title: Novel potent AMPA/kainate receptor antagonists: synthesis and anticonvulsant activity of a series of 2-[(4-alkylsemicarbazono)-(4-amino-phenyl)methyl]-4,5-methylenedioxyphenylacetic acid alkyl esters.

Journal: Journal of medicinal chemistry 20020926

Title: Suppression by zinc of AMPA receptor-mediated synaptic transmission in the retina.

Journal: Journal of neurophysiology 20020901

Title: Comparison of spontaneous and evoked epileptiform activity in three in vitro epilepsy models.

Journal: Brain research 20020802

Title: Molsidomine potentiates the protective activity of GYKI 52466, a non-NMDA antagonist, MK-801, a non-competitive NMDA antagonist, and riluzole against electroconvulsions in mice.

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

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: The non-competitive AMPA receptor antagonist (GYKI 52466) blocks quisqualate-induced acetylcholine release from the rat hippocampus and striatum: an in vivo microdialysis study.

Journal: Neurochemistry international 20020401

Title: Somatostatin stimulates striatal acetylcholine release by glutamatergic receptors: an in vivo microdialysis study.

Journal: Neurochemistry international 20020301

Title: A non-excitatory paradigm of glutamate toxicity.

Journal: Journal of neurophysiology 20020301

Title: Effects of phencyclidine (PCP) and MK 801 on the EEGq in the prefrontal cortex of conscious rats; antagonism by clozapine, and antagonists of AMPA-, alpha(1)- and 5-HT(2A)-receptors.

Journal: British journal of pharmacology 20020101

Title: The Neurobiology and Neuropharmacology of Alzheimer's Disease. The ASPET - Ray Fuller Symposium. New Orleans, LA, USA, April 19-20, 2002.

Journal: CNS drug reviews 20020101

Title: beta-Adrenoceptor blockade enhances the anticonvulsant effect of glutamate receptor antagonists against maximal electroshock.

Journal: European journal of pharmacology 20011116

Title: Early activation of Ca(2+)-permeable AMPA receptors reduces neurite outgrowth in embryonic chick retinal neurons.

Journal: Journal of neurobiology 20011115

Title: Modulation of excitatory synaptic transmission by GABA(C) receptor-mediated feedback in the mouse inner retina.

Journal: Journal of neurophysiology 20011101

Title: Comparison of excitotoxic profiles of ATPA, AMPA, KA and NMDA in organotypic hippocampal slice cultures.

Journal: Brain research 20011026

Title: Group I metabotropic glutamate receptors limit AMPA receptor-mediated oligodendrocyte progenitor cell death.

Journal: European journal of pharmacology 20010727

Title: In vivo pharmacology of BIIR 561 CL, a novel combined antagonist of AMPA receptors and voltage-dependent Na(+) channels.

Journal: British journal of pharmacology 20010701

Title: Ampa/kainate receptor activation mediates hypoxic oligodendrocyte death and axonal injury in cerebral white matter.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20010615

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: Analysis of spontaneous EPSCs in retinal horizontal cells of the carp.

Journal: Neuroscience research 20010501

Title: GYKI 52466 has positive modulatory effects on AMPA receptors.

Journal: Brain research 20010223

Title: In vivo, the direct and seizure-induced neuronal cytotoxicity of kainate and AMPA is modified by the non-competitive antagonist, GYKI 52466.

Journal: Brain research 20010126

Title: Role of AMPA and GluR5 kainate receptors in the development and expression of amygdala kindling in the mouse.

Journal: Neuropharmacology 20010101

Title: Presynaptic alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionate receptor-mediated stimulation of glutamate and GABA release in the rat striatum in vivo: a dual-label microdialysis study.

Journal: Neuroscience 20010101

Title: Na(+)-K(+)-ATPase inhibition and depolarization induce glutamate release via reverse Na(+)-dependent transport in spinal cord white matter.

Journal: Neuroscience 20010101

Title: Functionally different AMPA-type glutamate receptors in morphologically identified neurons in rat superficial superior colliculus.

Journal: Neuroscience 20010101

Title: Interaction of GYKI 52466, a selective non-competitive antagonist of AMPA/kainate receptors, with conventional antiepileptic drugs in amygdala-kindled seizures in rats.

Journal: Polish journal of pharmacology 20010101

Title: AMPA-preferring receptors mediate excitatory non-NMDA responses of primate retinal ganglion cells.

Journal: Visual neuroscience 20010101

Title: Effect of ionotropic glutamate receptors antagonists on the modifications in extracellular glutamate and aspartate levels during picrotoxin seizures: a microdialysis study in freely moving rats.

Journal: Neurochemistry international 20001001

Title: Effects of AMPA/kainate glutamate receptor antagonists on cocaine-induced convulsions and lethality in mice.

Journal: European journal of pharmacology 19991215

Title: Anticonvulsants for soman-induced seizure activity.

Journal: Journal of biomedical science 19990101

Title: The vital dye Evans blue mimics limbic seizures induced by kainate or pilocarpine.

Journal: Brain research 19970411

Title: Morphine-induced catalepsy is augmented by NMDA receptor antagonists, but is partially attenuated by an AMPA receptor antagonist.

Journal: European journal of pharmacology 19960111

Title: Some central effects of GYKI 52466, a non-competitive AMPA receptor antagonist.

Journal: Polish journal of pharmacology 19950101

Title: Effects of the non-NMDA antagonists NBQX and the 2,3-benzodiazepine GYKI 52466 on different seizure types in mice: comparison with diazepam and interactions with flumazenil.

Journal: British journal of pharmacology 19941201

Title: The AMPA receptor antagonist GYKI 52466 reverses the anti-cataleptic effects of the competitive NMDA receptor antagonist CGP 37849.

Journal: European journal of pharmacology 19940502

Title: The non-NMDA glutamate receptor antagonist GYKI 52466 counteracts locomotor stimulation and anticataleptic activity induced by the NMDA antagonist dizocilpine.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 19931101

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Tags:102771-26-6 Molecular Formula|102771-26-6 MDL|102771-26-6 SMILES|102771-26-6 Benzenamine, 4-(8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)-