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82499-00-1,MFCD00055073
Catalog No.:AA0035SG

82499-00-1 | Methyl 6,7-dimethoxy-4-ethyl-β-carboline-3-carboxylate

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0035SG
Chemical Name:
Methyl 6,7-dimethoxy-4-ethyl-β-carboline-3-carboxylate
CAS Number:
82499-00-1
Molecular Formula:
C17H18N2O4
Molecular Weight:
314.3358
MDL Number:
MFCD00055073
SMILES:
COC(=O)c1ncc2c(c1CC)c1cc(OC)c(cc1[nH]2)OC
Properties
Properties
 
Storage:
Room Temperature;  

Computed Properties
 
Complexity:
433  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
5  
XLogP3:
3.2  

Literature

Title: DMCM, a benzodiazepine site inverse agonist, improves active avoidance and motivation in the rat.

Journal: Behavioural brain research 20121201

Title: Rats with different thresholds to clonic convulsions induced by DMCM differ in the binding of [3H]-MK-801 and [3H]-ouabain in the membranes of brain regions.

Journal: Neurochemical research 20120701

Title: Rats with different thresholds for DMCM-induced clonic convulsions differ in the sleep-time of diazepam and [(3)H]-Ro 15-4513 binding.

Journal: Epilepsy research 20120201

Title: Actions of two GABAA receptor benzodiazepine-site ligands that are mediated via non-γ2-dependent modulation.

Journal: European journal of pharmacology 20110901

Title: Characterization of GABA(A) receptors expressed in glial cell membranes of adult mouse neocortex using a Xenopus oocyte microtransplantation expression system.

Journal: Journal of neuroscience methods 20110515

Title: Disulphide trapping of the GABA(A) receptor reveals the importance of the coupling interface in the action of benzodiazepines.

Journal: British journal of pharmacology 20110201

Title: Removal of GABA(A) receptor γ2 subunits from parvalbumin neurons causes wide-ranging behavioral alterations.

Journal: PloS one 20110101

Title: Developing dual functional allosteric modulators of GABA(A) receptors.

Journal: Bioorganic & medicinal chemistry 20101201

Title: Anticonvulsant effects of methyl ethyl ketone and diethyl ketone in several types of mouse seizure models.

Journal: European journal of pharmacology 20100910

Title: Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Journal: Nature chemical biology 20091001

Title: Similar anxiolytic-like effects following intra-amygdala infusions of benzodiazepine receptor agonist and antagonist: evidence for the release of an endogenous benzodiazepine inverse agonist in mice exposed to elevated plus-maze test.

Journal: Brain research 20090424

Title: Expression levels of the alpha4 subunit of the GABA(A) receptor in differentiated neuroblastoma cells are correlated with GABA-gated current.

Journal: Neuropharmacology 20090101

Title: A high-throughput functional assay for characterization of gamma-aminobutyric acid(A) channel modulators using cryopreserved transiently transfected cells.

Journal: Assay and drug development technologies 20081201

Title: PWZ-029, a compound with moderate inverse agonist functional selectivity at GABA(A) receptors containing alpha5 subunits, improves passive, but not active, avoidance learning in rats.

Journal: Brain research 20080507

Title: Structural mechanisms underlying benzodiazepine modulation of the GABA(A) receptor.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20080326

Title: Chemoconvulsant-induced seizure susceptibility: toward a common genetic basis?

Journal: Epilepsia 20070101

Title: Effects of stress modulation on morphine-induced conditioned place preferences and plasma corticosterone levels in Fischer, Lewis, and Sprague-Dawley rat strains.

Journal: Psychopharmacology 20061201

Title: Mechanism of action of benzodiazepines on GABAA receptors.

Journal: British journal of pharmacology 20060801

Title: Pharmacological properties of GABAA receptors containing gamma1 subunits.

Journal: Molecular pharmacology 20060201

Title: Behavioral differences between subgroups of rats with high and low threshold to clonic convulsions induced by DMCM, a benzodiazepine inverse agonist.

Journal: Pharmacology, biochemistry, and behavior 20051101

Title: Negative GABA(A) modulators attenuate the discriminative stimulus effects of benzodiazepines and the neuroactive steroid pregnanolone in rhesus monkeys.

Journal: Psychopharmacology 20051001

Title: Targeted invalidation of CCK2 receptor gene induces anxiolytic-like action in light-dark exploration, but not in fear conditioning test.

Journal: Psychopharmacology 20050901

Title: Bidirectional effects of benzodiazepine binding site ligands on active avoidance acquisition and retention: differential antagonism by flumazenil and beta-CCt.

Journal: Psychopharmacology 20050701

Title: Bidirectional effects of benzodiazepine binding site ligands in the passive avoidance task: differential antagonism by flumazenil and beta-CCt.

Journal: Behavioural brain research 20050330

Title: Agonistic effects of the beta-carboline DMCM revealed in GABA(A) receptor gamma 2 subunit F77I point-mutated mice.

Journal: Neuropharmacology 20050301

Title: An orally bioavailable, functionally selective inverse agonist at the benzodiazepine site of GABAA alpha5 receptors with cognition enhancing properties.

Journal: Journal of medicinal chemistry 20041118

Title: Compounds exhibiting selective efficacy for different beta subunits of human recombinant gamma-aminobutyric acid A receptors.

Journal: The Journal of pharmacology and experimental therapeutics 20041101

Title: Electrophysiological properties of mouse horizontal cell GABAA receptors.

Journal: Journal of neurophysiology 20041101

Title: Bidirectional effects of benzodiazepine binding site ligands in the elevated plus-maze: differential antagonism by flumazenil and beta-CCt.

Journal: Pharmacology, biochemistry, and behavior 20041001

Title: Seizure susceptibility to various convulsant stimuli in dystrophin-deficient mdx mice.

Journal: Neuroscience research 20040901

Title: 3,4-Dihydronaphthalen-1(2H)-ones: novel ligands for the benzodiazepine site of alpha5-containing GABAA receptors.

Journal: Bioorganic & medicinal chemistry letters 20040607

Title: Seizure susceptibility to various convulsant stimuli of knockout interleukin-6 mice.

Journal: Pharmacology, biochemistry, and behavior 20040401

Title: Neuroscience. Blocking plasticity in the visual cortex.

Journal: Science (New York, N.Y.) 20040312

Title: Columnar architecture sculpted by GABA circuits in developing cat visual cortex.

Journal: Science (New York, N.Y.) 20040312

Title: Identification of a residue in the gamma-aminobutyric acid type A receptor alpha subunit that differentially affects diazepam-sensitive and -insensitive benzodiazepine site binding.

Journal: Journal of neurochemistry 20040301

Title: Potential pleiotropic effects of Mpdz on vulnerability to seizures.

Journal: Genes, brain, and behavior 20040201

Title: Augmentation of the NO-cGMP cascade induces anxiogenic-like effect in mice.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20031201

Title: Validation of a modified mirrored chamber sensitive to anxiolytics and anxiogenics in mice.

Journal: Psychopharmacology 20030901

Title: Benzodiazepine agonist and inverse agonist coupling in GABAA receptors antagonized by increased atmospheric pressure.

Journal: European journal of pharmacology 20030523

Title: Identification of a novel, selective GABA(A) alpha5 receptor inverse agonist which enhances cognition.

Journal: Journal of medicinal chemistry 20030522

Title: Mechanism-based pharmacokinetic/pharmacodynamic modeling of the electroencephalogram effects of GABAA receptor modulators: in vitro-in vivo correlations.

Journal: The Journal of pharmacology and experimental therapeutics 20030101

Title: Functional characterization of GABA(A) receptors in neonatal hypothalamic brain slice.

Journal: Journal of neurophysiology 20021001

Title: Contribution of the alpha1-GABA(A) receptor subtype to the pharmacological actions of benzodiazepine site inverse agonists.

Journal: Neuropharmacology 20020901

Title: Stress-induced deoxycorticosterone-derived neurosteroids modulate GABA(A) receptor function and seizure susceptibility.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20020501

Title: 3-Heteroaryl-2-pyridones: benzodiazepine site ligands with functional delectivity for alpha 2/alpha 3-subtypes of human GABA(A) receptor-ion channels.

Journal: Journal of medicinal chemistry 20020425

Title: 6,7-Dihydro-2-benzothiophen-4(5H)-ones: a novel class of GABA-A alpha5 receptor inverse agonists.

Journal: Journal of medicinal chemistry 20020314

Title: Daily treatment with diazepam differentially modifies sensitivity to the effects of gamma-aminobutyric acid(A) modulators on schedule-controlled responding in rhesus monkeys.

Journal: The Journal of pharmacology and experimental therapeutics 20020301

Title: Pharmacological heterogeneity of gamma-aminobutyric acid receptors during development suggests distinct classes of rat cerebellar granule cells in situ.

Journal: Neuropharmacology 20020101

Title: Synthesis of novel GABA uptake inhibitors. Part 6: preparation and evaluation of N-Omega asymmetrically substituted nipecotic acid derivatives.

Journal: Bioorganic & medicinal chemistry 20011101

Title: GABA(A) receptor epsilon-subunit may confer benzodiazepine insensitivity to the caudal aspect of the nucleus tractus solitarii of the rat.

Journal: The Journal of physiology 20011101

Title: Protective effects of cannabinoid receptor agonists against cocaine and other convulsant-induced toxic behavioural symptoms.

Journal: The Journal of pharmacy and pharmacology 20011101

Title: Influence of benzodiazepine binding site ligands on fear-conditioned contextual memory.

Journal: European journal of pharmacology 20010824

Title: Synthesis of novel gamma-aminobutyric acid (GABA) uptake inhibitors. 5.(1) Preparation and structure-activity studies of tricyclic analogues of known GABA uptake inhibitors.

Journal: Journal of medicinal chemistry 20010621

Title: Functional pharmacology of GABA(A) receptors containing the chicken brain gamma 4 subunit.

Journal: European journal of pharmacology 20010504

Title: The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.

Journal: Journal of neurochemistry 20010101

Title: Pain and negative affect: evidence the inverse benzodiazepine agonist DMCM inhibits pain and learning in rats.

Journal: Psychopharmacology 20010101

Title: Pharmacophore/receptor models for GABA(A)/BzR subtypes (alpha1beta3gamma2, alpha5beta3gamma2, and alpha6beta3gamma2) via a comprehensive ligand-mapping approach.

Journal: Journal of medicinal chemistry 20000113

Title: Structure-activity relationships and molecular modeling analysis of flavonoids binding to the benzodiazepine site of the rat brain GABA(A) receptor complex.

Journal: Journal of medicinal chemistry 19991021

Title: Evidence for a unique profile of levetiracetam in rodent models of seizures and epilepsy.

Journal: European journal of pharmacology 19980724

Title: Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (Zk 93423) at wild type and recombinant GABAA receptors.

Journal: Journal of medicinal chemistry 19980702

Title: Cocaine: evidence for NMDA-, beta-carboline- and dopaminergic-mediated seizures in mice.

Journal: Brain research 19980629

Title: Hypersusceptibility to DMCM-induced seizures during diazepam withdrawal in mice: evidence for upregulation of NMDA receptors.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 19980301

Title: The influence of the antidepressant pirlindole and its dehydro-derivative on the activity of monoamine oxidase A and GABAA receptor binding.

Journal: Journal of neural transmission. Supplementum 19980101

Title: Cerebellar gamma-aminobutyric acid type A receptors: pharmacological subtypes revealed by mutant mouse lines.

Journal: Molecular pharmacology 19970901

Title: Anticonvulsant doses of 2-chloro-N6-cyclopentyladenosine, an adenosine A1 receptor agonist, reduce GABAergic transmission in different areas of the mouse brain.

Journal: The Journal of pharmacology and experimental therapeutics 19931101

Title: [Effects of agonists and antagonists of benzodiazepine, GABA and NMDA receptors, on caffeine-induced seizures in mice].

Journal: Yakubutsu, seishin, kodo = Japanese journal of psychopharmacology 19920801

Title: Yohimbine-induced seizures involve NMDA and GABAergic transmission.

Journal: Neuropharmacology 19920401

Title: Relative anticonvulsant effects of GABAmimetic and GABA modulatory agents.

Journal: Epilepsia 19920101

Title: Nitrendipine decreases benzodiazepine withdrawal seizures but not the development of benzodiazepine tolerance or withdrawal signs.

Journal: British journal of pharmacology 19901101

Title: GABAA-receptor expressed from rat brain alpha- and beta-subunit cDNAs displays potentiation by benzodiazepine receptor ligands.

Journal: Brain research. Molecular brain research 19900801

Title: Adenosine receptor antagonism accounts for the seizure-prolonging effects of aminophylline.

Journal: Pharmacology, biochemistry, and behavior 19900801

Title: Anticonvulsant action of the beta-carboline abecarnil: studies in rodents and baboon, Papio papio.

Journal: The Journal of pharmacology and experimental therapeutics 19900401

Title: Ro 15-4513, a partial inverse agonist for benzodiazepine recognition sites, has proconflict and proconvulsant effects in the rat.

Journal: European journal of pharmacology 19890117

Title: Comparison of the anticonvulsant activities of ethosuximide, valproate, and a new anticonvulsant, thiobutyrolactone.

Journal: Epilepsia 19890101

Title: Enhanced sensitivity to beta-carboline inverse agonists in rats chronically treated with FG 7142.

Journal: Brain research bulletin 19870901

Title: Bidirectional effects of beta-carbolines in reflex epilepsy.

Journal: Brain research bulletin 19870901

Title: Different genes specify hyporesponsiveness to seizures induced by caffeine and the benzodiazepine inverse agonist, DMCM.

Journal: Pharmacology, biochemistry, and behavior 19870701

Title: Differential effects of gamma-hexachlorocyclohexane (lindane) on pharmacologically-induced seizures.

Journal: Archives of toxicology 19870401

Title: Coincidence of seizure susceptibility to caffeine and to the benzodiazepine inverse agonist, DMCM, in SWR and CBA inbred mice.

Journal: Pharmacology, biochemistry, and behavior 19870201

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Tags:82499-00-1 Molecular Formula|82499-00-1 MDL|82499-00-1 SMILES|82499-00-1 Methyl 6,7-dimethoxy-4-ethyl-β-carboline-3-carboxylate