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52809-07-1,MFCD00069337
Catalog No.:AA003518

52809-07-1 | L-Quisqualic Acid

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1mg
≥99%
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$80.00   $56.00
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5mg
≥99%
in stock  
$156.00   $109.00
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10mg
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$269.00   $188.00
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25mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003518
Chemical Name:
L-Quisqualic Acid
CAS Number:
52809-07-1
Molecular Formula:
C5H7N3O5
Molecular Weight:
189.1262
MDL Number:
MFCD00069337
SMILES:
OC(=O)[C@H](Cn1oc(=O)[nH]c1=O)N
Properties
Properties
 
Form:
Solid  
MP:
170 - 172C  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
265  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
-3.9  

Downstream Synthesis Route

[1]Chemicalandpharmaceuticalbulletin,1986,vol.34,p.1473-1478

[2]Phytochemistry,1990,vol.29,p.2507-2508

[3]Heterocycles,1984,vol.21,p.705

[4]Phytochemistry,1986,vol.25,p.2759-2764

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Title: Mutation-induced quisqualic acid and ibotenic acid affinity at the metabotropic glutamate receptor subtype 4: ligand selectivity results from a synergy of several amino acid residues.

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Title: Characterization of a domoic acid binding site from Pacific razor clam.

Journal: Aquatic toxicology (Amsterdam, Netherlands) 20040810

Title: Interaction between intrathecal gabapentin and adenosine in the formalin test of rats.

Journal: Journal of Korean medical science 20040801

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Title: A novel selective allosteric modulator potentiates the activity of native metabotropic glutamate receptor subtype 5 in rat forebrain.

Journal: The Journal of pharmacology and experimental therapeutics 20040501

Title: Analogues of homoibotenic acid show potent and selective activity following sensitisation by quisqualic acid.

Journal: European journal of pharmacology 20040319

Title: Differentiation of substrate and non-substrate inhibitors of transport system xc(-): an obligate exchanger of L-glutamate and L-cystine.

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Title: Effects of quisqualic acid on retinal ZENK expression induced by imposed defocus in the chick eye.

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Title: The effects of endogenous interleukin-10 on gray matter damage and the development of pain behaviors following excitotoxic spinal cord injury in the mouse.

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Title: Glutamate-mediated cytosolic calcium oscillations regulate a pulsatile prostaglandin release from cultured rat astrocytes.

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Journal: Journal of comparative physiology. A, Neuroethology, sensory, neural, and behavioral physiology 20030501

Title: Role of G protein-coupled receptor kinase 4 and beta-arrestin 1 in agonist-stimulated metabotropic glutamate receptor 1 internalization and activation of mitogen-activated protein kinases.

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Title: Age-related differences in NMDA/metabotropic glutamate receptor binding in rat substantia nigra.

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Journal: The international journal of neuropsychopharmacology 20030301

Title: Amino acid mutagenesis of the ligand binding site and the dimer interface of the metabotropic glutamate receptor 1. Identification of crucial residues for setting the activated state.

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Title: Neurohormonal and glutamatergic neuronal control of the cardioarterial valves in the isopod crustacean Bathynomus doederleini.

Journal: The Journal of experimental biology 20030201

Title: Ionotropic glutamate receptors in cerebral microvascular endothelium are functionally linked to heme oxygenase.

Journal: Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20030201

Title: The selective cyclooxygenase-2 inhibitor rofecoxib suppresses brain inflammation and protects cholinergic neurons from excitotoxic degeneration in vivo.

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Title: Group-I metabotropic glutamate receptors, mGlu1a and mGlu5a, couple to extracellular signal-regulated kinase (ERK) activation via distinct, but overlapping, signalling pathways.

Journal: Journal of neurochemistry 20021201

Title: A pharmacological analysis of the contractile effects of glutamate on rat and human isolated gut smooth muscle strips.

Journal: Methods and findings in experimental and clinical pharmacology 20021201

Title: Lead can inhibit NMDA-, K(+)-, QA/KA-induced increases in intracellular free Ca2+ in cultured rat hippocampal neurons.

Journal: Biomedical and environmental sciences : BES 20021201

Title: Culturing and characterization of astrocytes isolated from juvenile rainbow trout (Oncorhynchus mykiss).

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20020901

Title: VEGA: a versatile program to convert, handle and visualize molecular structure on Windows-based PCs.

Journal: Journal of molecular graphics & modelling 20020801

Title: Common and selective molecular determinants involved in metabotopic glutamate receptor agonist activity.

Journal: Journal of medicinal chemistry 20020718

Title: Ionotropic glutamate receptors mediate juvenile hormone synthesis in the cockroach, Diploptera punctata.

Journal: Insect biochemistry and molecular biology 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: 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: Internalization of metabotropic glutamate receptor in C6 cells through clathrin-coated vesicles.

Journal: Brain research. Molecular brain research 20020227

Title: Expression of the nerve growth factor receptors TrkA and p75NTR in the visual cortex of the rat: development and regulation by the cholinergic input.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20020201

Title: Glutamate receptors on the somata of dorsal unpaired median neurons in cockroach, Periplaneta americana, thoracic ganglia.

Journal: Zoological science 20020201

Title: Characterization of an N-terminal secreted domain of the type-1 human metabotropic glutamate receptor produced by a mammalian cell line.

Journal: Journal of neurochemistry 20020101

Title: A novel binding assay for metabotropic glutamate receptors using [3H] L-quisqualic acid and recombinant receptors.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101

Title: Use of excitotoxins to lesion the hippocampus: update.

Journal: Hippocampus 20020101

Title: Nitric oxide synthase inhibition and glutamate binding in quinolinate-lesioned rat hippocampus.

Journal: Physiological research 20020101

Title: Influence of serotonin on the glutamate-induced excitations of secondary vestibular neurons in the rat.

Journal: Experimental neurology 20011201

Title: Positive allosteric modulators of metabotropic glutamate 1 receptor: characterization, mechanism of action, and binding site.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20011106

Title: Glutamate receptor desensitization block potentiates the stimulated GABA release through external Ca2+-independent mechanisms from granule cells of olfactory bulb.

Journal: Neurochemical research 20011101

Title: Protective effect of excitatory amino acids on cold-restraint stress-induced gastric ulcers in mice: role of cyclic nucleotides.

Journal: Digestive diseases and sciences 20011001

Title: Binding of the glutamate carboxypeptidase II (NAALADase) inhibitor 2-PMPA to rat brain membranes.

Journal: European journal of pharmacology 20010914

Title: Excitotoxic model of post-traumatic syringomyelia in the rat.

Journal: Spine 20010901

Title: Physiological and pharmacological characteristics of quisqualic acid-induced K(+)-current response in the ganglion cells of Aplysia.

Journal: The Japanese journal of physiology 20010801

Title: Differential effects of glutamate agonists and D-aspartate on oxytocin release from hypothalamus and posterior pituitary of male rats.

Journal: Endocrine 20010801

Title: Conditions affecting the onset, severity, and progression of a spontaneous pain-like behavior after excitotoxic spinal cord injury.

Journal: The journal of pain : official journal of the American Pain Society 20010801

Title: Expression of c-fos mRNA is increased and related to dynorphin mRNA expression following excitotoxic spinal cord injury in the rat.

Journal: Neuroscience letters 20010720

Title: Dibutyryl-cAMP (dbcAMP) up-regulates astrocytic chloride-dependent L-[3H]glutamate transport and expression of both system xc(-) subunits.

Journal: Journal of neurochemistry 20010701

Title: Reassessment of the Ca2+ sensing property of a type I metabotropic glutamate receptor by simultaneous measurement of inositol 1,4,5-trisphosphate and Ca2+ in single cells.

Journal: The Journal of biological chemistry 20010601

Title: Enhanced inducible mGlu1alpha receptor expression in Chinese hamster ovary cells.

Journal: Journal of neurochemistry 20010601

Title: NO-flurbiprofen attenuates excitotoxin-induced brain inflammation, and releases nitric oxide in the brain.

Journal: Japanese journal of pharmacology 20010601

Title: Characterization of glutamate-gated chloride channels in the pharynx of wild-type and mutant Caenorhabditis elegans delineates the role of the subunit GluCl-alpha2 in the function of the native receptor.

Journal: Molecular pharmacology 20010501

Title: Inhibition of choline acetyltransferase by excitatory amino acids as a possible mechanism for cholinergic dysfunction in the central nervous system.

Journal: Journal of neurochemistry 20010501

Title: A Na+-dependent electrogenic glutamate transporter current in voltage-clamped cells of corpora allata in the cricket Gryllus bimaculatus.

Journal: Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20010501

Title: Cloning and characterization of a human orphan family C G-protein coupled receptor GPRC5D.

Journal: Biochimica et biophysica acta 20010416

Title: Cell type-specific differences in the coupling of recombinant mGlu1alpha receptors to endogenous G protein sub-populations.

Journal: Neuropharmacology 20010401

Title: An activity-dependent switch from facilitation to inhibition in the control of excitotoxicity by group I metabotropic glutamate receptors.

Journal: The European journal of neuroscience 20010401

Title: The effects of nucleus basalis magnocellularis lesions in Long-Evans hooded rats on two learning set formation tasks, delayed matching-to-sample learning, and open-field activity.

Journal: Behavioral neuroscience 20010401

Title: [Synthesis and release of N-acetylaspartyl glutamate (NAAG) in medial giant axons in crayfish].

Journal: Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20010401

Title: Tetanic stimulation and metabotropic glutamate receptor agonists modify synaptic responses and protein kinase activity in rat auditory cortex.

Journal: Brain research 20010316

Title: Methylmercury inhibits the in vitro uptake of the glutathione precursor, cystine, in astrocytes, but not in neurons.

Journal: Brain research 20010309

Title: Characterization with [3H]quisqualate of group I metabotropic glutamate receptor subtype in rat central and peripheral excitable tissues.

Journal: Neurochemistry international 20010301

Title: Effects of interleukin-10 (IL-10) on pain behavior and gene expression following excitotoxic spinal cord injury in the rat.

Journal: Experimental neurology 20010301

Title: Cajal-Retzius cells in early postnatal mouse cortex selectively express functional metabotropic glutamate receptors.

Journal: The European journal of neuroscience 20010301

Title: Metabotropic glutamate receptor type 1alpha and tubulin assemble into dynamic interacting complexes.

Journal: Journal of neurochemistry 20010201

Title: Spinal and supraspinal changes in opioid mRNA expression are related to the onset of pain behaviors following excitotoxic spinal cord injury.

Journal: Pain 20010201

Title: Covalent and noncovalent interactions mediate metabotropic glutamate receptor mGlu5 dimerization.

Journal: Molecular pharmacology 20010101

Title: Expression of ionotropic glutamate receptors in the retina of the rdta transgenic mouse.

Journal: BMC neuroscience 20010101

Title: The role of kainic acid/AMPA and metabotropic glutamate receptors in the regulation of opioid mRNA expression and the onset of pain-related behavior following excitotoxic spinal cord injury.

Journal: Neuroscience 20010101

Title: Synthesis and release of N-acetylaspartylglutamate (NAAG) by crayfish nerve fibers: implications for axon-glia signaling.

Journal: Neuroscience 20010101

Title: L-Quisqualic acid transport into hippocampal neurons by a cystine-sensitive carrier is required for the induction of quisqualate sensitization.

Journal: Neuroscience 20010101

Title: Mechanisms for clearance of released N-acetylaspartylglutamate in crayfish nerve fibers: implications for axon-glia signaling.

Journal: Neuroscience 20010101

Title: Cognitive effects of neurotoxic lesions of the nucleus basalis magnocellularis in rats: differential roles for corticopetal versus amygdalopetal projections.

Journal: Neurotoxicity research 20010101

Title: Characterization of [(3)H]Quisqualate binding to recombinant rat metabotropic glutamate 1a and 5a receptors and to rat and human brain sections.

Journal: Journal of neurochemistry 20001201

Title: Pharmacological characterization of the rat metabotropic glutamate receptor type 8a revealed strong similarities and slight differences with the type 4a receptor.

Journal: European journal of pharmacology 20000407

Title: Effect of the umami peptides on the ligand binding and function of rat mGlu4a receptor might implicate this receptor in the monosodium glutamate taste transduction.

Journal: British journal of pharmacology 19991101

Title: 2-Methyl-6-(phenylethynyl)-pyridine (MPEP), a potent, selective and systemically active mGlu5 receptor antagonist.

Journal: Neuropharmacology 19991001

Title: Propofol modulates the effects of chemoconvulsants acting at GABAergic, glycinergic, and glutamate receptor subtypes.

Journal: Anesthesiology 19951001

Title: Pharmacological analysis of 4-carboxyphenylglycine derivatives: comparison of effects on mGluR1 alpha and mGluR5a subtypes.

Journal: Neuropharmacology 19950801

Title: Felbamate displays in vitro antiepileptic effects as a broad spectrum excitatory amino acid receptor antagonist.

Journal: European journal of pharmacology 19941227

Title: Benzothiadiazides inhibit rapid glutamate receptor desensitization and enhance glutamatergic synaptic currents.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 19930901

Title: A pharmacological characterization of the mGluR1 alpha subtype of the metabotropic glutamate receptor expressed in a cloned baby hamster kidney cell line.

Journal: Brain research 19930813

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: The involvement of excitatory amino acid receptors within the prepiriform cortex in pilocarpine-induced limbic seizures in rats.

Journal: Experimental brain research 19880101

Title: Amino acid neurotoxicity: relationship to neuronal depolarization in rat cerebellar slices.

Journal: Neuroscience 19860601

Title: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex.

Journal: British journal of pharmacology 19850201

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Title: H Bräuner-Osborne, et al. Ligands for Glutamate Receptors: Design and Therapeutic Prospects. J Med Chem. 2000 Jul 13;43(14):2609-45.

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