Home Carboxys Benzeneacetic acid, α-amino-4-carboxy-α-methyl-

Benzeneacetic acid, α-amino-4-carboxy-α-methyl-

CAS No.:
146669-29-6
Catalog Number:
AG001E7P
Molecular Formula:
C10H11NO4
Molecular Weight:
209.1986
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%
1 week
United States
$168
- +
10mg
98%
1 week
United States
$210
- +
25mg
98%
1 week
United States
$390
- +
50mg
98%
1 week
United States
$654
- +
100mg
98%
1 week
United States
$1140
- +
Product Description
Catalog Number:
AG001E7P
Chemical Name:
Benzeneacetic acid, α-amino-4-carboxy-α-methyl-
CAS Number:
146669-29-6
Molecular Formula:
C10H11NO4
Molecular Weight:
209.1986
MDL Number:
MFCD00210205
IUPAC Name:
4-(1-amino-1-carboxyethyl)benzoic acid
InChI:
InChI=1S/C10H11NO4/c1-10(11,9(14)15)7-4-2-6(3-5-7)8(12)13/h2-5H,11H2,1H3,(H,12,13)(H,14,15)
InChI Key:
DNCAZYRLRMTVSF-UHFFFAOYSA-N
SMILES:
OC(=O)c1ccc(cc1)C(C(=O)O)(N)C
Properties
Complexity:
271  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
209.069g/mol
Formal Charge:
0
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
209.201g/mol
Monoisotopic Mass:
209.069g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
101A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
-2  
Literature
Title Journal
Electrophysiological and behavioral effects of group I metabotropic glutamate receptors on pallidal neurons in rats. Brain research 20121005
Rescue of synaptic plasticity and spatial learning deficits in the hippocampus of Homer1 knockout mice by recombinant Adeno-associated viral gene delivery of Homer1c. Neurobiology of learning and memory 20120101
Differential involvement of mGluR1 and mGluR5 in memory reconsolidation and retrieval in a passive avoidance task in 1-day old chicks. Neurobiology of learning and memory 20120101
Pain-related deactivation of medial prefrontal cortical neurons involves mGluR1 and GABA(A) receptors. Journal of neurophysiology 20111101
Contribution of excitatory amino acid receptors of the retrotrapezoid nucleus to the sympathetic chemoreflex in rats. Experimental physiology 20111001
Molecular changes associated with hippocampal long-lasting depression induced by the serine protease subtilisin-A. The European journal of neuroscience 20111001
Astrocytes display complex and localized calcium responses to single-neuron stimulation in the hippocampus. The Journal of neuroscience : the official journal of the Society for Neuroscience 20110615
Activation of group I metabotropic glutamate receptors modulates locomotor-related motoneuron output in mice. Journal of neurophysiology 20110501
Group I mGluR agonist-evoked long-term potentiation in hippocampal oriens interneurons. The Journal of neuroscience : the official journal of the Society for Neuroscience 20110413
Parasagittally aligned, mGluR1-dependent patches are evoked at long latencies by parallel fiber stimulation in the mouse cerebellar cortex in vivo. Journal of neurophysiology 20110401
Synaptic activation of mGluR1 generates persistent depression of a fast after-depolarizing potential in CA3 pyramidal neurons. The European journal of neuroscience 20110301
Mitochondrial reactive oxygen species are activated by mGluR5 through IP3 and activate ERK and PKA to increase excitability of amygdala neurons and pain behavior. The Journal of neuroscience : the official journal of the Society for Neuroscience 20110119
Metabotropic glutamate receptors transduce signals for neurite outgrowth after binding of the prion protein to laminin γ1 chain. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20110101
Regulation of system x(c)(-)activity and expression in astrocytes by interleukin-1β: implications for hypoxic neuronal injury. Glia 20101115
NMDA receptor, PKC and ERK prevent fos expression induced by the activation of group I metabotropic glutamate receptors in the spinal trigeminal subnucleus oralis. Molecules and cells 20101101
Endocannabinoids potentiate synaptic transmission through stimulation of astrocytes. Neuron 20101006
mGluR1 antagonist decreased NADPH oxidase activity and superoxide production after transient focal cerebral ischemia. Journal of neurochemistry 20100901
Distinct modes of modulation of GABAergic transmission by Group I metabotropic glutamate receptors in rat entorhinal cortex. Hippocampus 20100801
Modulators of metabotropic glutamate receptors microinfused into perirhinal cortex: anticonvulsant effects in rats challenged with soman. European journal of pharmacology 20100625
[Activation of mGluRI in neutrophils promotes the adherence of neutrophils to endothelial cells]. Sheng li xue bao : [Acta physiologica Sinica] 20100625
Potent homocysteine-induced ERK phosphorylation in cultured neurons depends on self-sensitization via system Xc(-). Toxicology and applied pharmacology 20100115
Estradiol-induced estrogen receptor-alpha trafficking. The Journal of neuroscience : the official journal of the Society for Neuroscience 20091202
An interaction of oxytocin receptors with metabotropic glutamate receptors in hypothalamic astrocytes. Journal of neuroendocrinology 20091201
Long-term potentiation of the responses to parallel fiber stimulation in mouse cerebellar cortex in vivo. Neuroscience 20090901
Excitatory actions of noradrenaline and metabotropic glutamate receptor activation in granule cells of the accessory olfactory bulb. Journal of neurophysiology 20090801
Odor-induced persistent discharge of mitral cells in the mouse olfactory bulb. Journal of neurophysiology 20090401
Impact of protein kinase C activation on epileptiform activity in the hippocampal slice. Epilepsy research 20081101
Spinal Metabotropic Glutamate Receptors (mGluRs) are Involved in the Melittin-induced Nociception in Rats. The Korean journal of physiology & pharmacology : official journal of the Korean Physiological Society and the Korean Society of Pharmacology 20081001
Activation of group I metabotropic glutamate receptors induces long-term depression in the hippocampal CA1 region of adult rats in vitro. Neuroscience research 20080901
mGluR1 antagonist decreases tyrosine phosphorylation of NMDA receptor and attenuates infarct size after transient focal cerebral ischemia. Journal of neurochemistry 20080601
Dopamine D1 receptors and group I metabotropic glutamate receptors contribute to the induction of long-term potentiation in the nucleus accumbens. Neuropharmacology 20080401
Developmental decrease in short-term facilitation at Schaffer collateral synapses in hippocampus is mGluR1 sensitive. Journal of neurophysiology 20080201
A role for protein kinase A and protein kinase M zeta in muscarinic acetylcholine receptor-initiated persistent synaptic enhancement in rat hippocampus in vivo. Neuroscience 20080124
Selective induction of metabotropic glutamate receptor 1- and metabotropic glutamate receptor 5-dependent chemical long-term potentiation at oriens/alveus interneuron synapses of mouse hippocampus. Neuroscience 20080102
Subtype selective antagonism of substantia nigra pars compacta Group I metabotropic glutamate receptors protects the nigrostriatal system against 6-hydroxydopamine toxicity in vivo. Journal of neurochemistry 20071101
Differential roles of hippocampal metabotropic glutamate receptors 1 and 5 in inhibitory avoidance learning. Neurobiology of learning and memory 20071001
Membrane estrogen receptor-alpha interactions with metabotropic glutamate receptor 1a modulate female sexual receptivity in rats. The Journal of neuroscience : the official journal of the Society for Neuroscience 20070829
Recurrent dendrodendritic inhibition of accessory olfactory bulb mitral cells requires activation of group I metabotropic glutamate receptors. The Journal of neuroscience : the official journal of the Society for Neuroscience 20070523
An influence of ligands of metabotropic glutamate receptor subtypes on parkinsonian-like symptoms and the striatopallidal pathway in rats. Amino acids 20070201
The mGlu1 antagonist CPCCOEt enhances the climbing fibre response in Purkinje neurones independently of glutamate receptors. Neuropharmacology 20070201
Peripheral mGluR5 antagonist attenuated craniofacial muscle pain and inflammation but not mGluR1 antagonist in lightly anesthetized rats. Brain research bulletin 20061016
Nucleus- and species-specific properties of the slow (<1 Hz) sleep oscillation in thalamocortical neurons. Neuroscience 20060825
Dynamic translational and proteasomal regulation of fragile X mental retardation protein controls mGluR-dependent long-term depression. Neuron 20060817
mGluR1/5 subtype-specific calcium signalling and induction of long-term potentiation in rat hippocampal oriens/alveus interneurones. The Journal of physiology 20060815
Group I mGlu receptor stimulation inhibits activation-induced cell death of human T lymphocytes. British journal of pharmacology 20060701
Olfactory nerve-evoked, metabotropic glutamate receptor-mediated synaptic responses in rat olfactory bulb mitral cells. Journal of neurophysiology 20060401
Antidepressant-like effects of baclofen and LY367385 in the forced swim test in rats. Pharmacological reports : PR 20060101
Altered long-term synaptic plasticity and kainate-induced Ca2+ transients in the substantia gelatinosa neurons in GLU(K6)-deficient mice. Brain research. Molecular brain research 20051207
The inhibition of glycogen synthase kinase 3beta by a metabotropic glutamate receptor 5 mediated pathway confers neuroprotection to Abeta peptides. Journal of neurochemistry 20051201
Down-regulation of metabotropic glutamate receptor 1alpha in globus pallidus and substantia nigra of parkinsonian monkeys. The European journal of neuroscience 20051201
Role of peripheral group I and II metabotropic glutamate receptors in IL-1beta-induced mechanical allodynia in the orofacial area of conscious rats. Pain 20051101
Signal transduction pathways of group I metabotropic glutamate receptor-induced long-term depression at sensory spinal synapses. Pain 20051101
Glutamatergic receptors of the rostral ventrolateral medulla are involved in the ventilatory response to hypoxia. Respiratory physiology & neurobiology 20050415
Metabotropic glutamate receptors and dopamine receptors cooperate to enhance extracellular signal-regulated kinase phosphorylation in striatal neurons. The Journal of neuroscience : the official journal of the Society for Neuroscience 20050413
Comparison of metabotropic glutamate receptor responses at segmental and descending inputs to motoneurons in neonatal rat spinal cord. The Journal of pharmacology and experimental therapeutics 20050201
Pharmacological antagonism of metabotropic glutamate receptor 1 regulates long-term potentiation and spatial reference memory in the dentate gyrus of freely moving rats via N-methyl-D-aspartate and metabotropic glutamate receptor-dependent mechanisms. The European journal of neuroscience 20050101
Periaqueductal grey CB1 cannabinoid and metabotropic glutamate subtype 5 receptors modulate changes in rostral ventromedial medulla neuronal activities induced by subcutaneous formalin in the rat. Neuroscience 20050101
Repeated administration of group I mGluR antagonists prevents seizure-induced long-term aberrations in hippocampal synaptic plasticity. Neuropharmacology 20050101
Group I metabotropic glutamate receptors reduce excitotoxic injury and may facilitate neurogenesis. Neuropharmacology 20050101
The metabotropic glutamate receptor 5 is necessary for late-phase long-term potentiation in the hippocampal CA1 region. Brain research 20041001
Glutamatergic neurotransmission modulates hypoxia-induced hyperventilation but not anapyrexia. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20041001
Excitation of cerebellar interneurons by group I metabotropic glutamate receptors. Journal of neurophysiology 20040901
Activation of the phosphoinositide 3-kinase-Akt-mammalian target of rapamycin signaling pathway is required for metabotropic glutamate receptor-dependent long-term depression. The Journal of neuroscience : the official journal of the Society for Neuroscience 20040714
Group I metabotropic glutamate receptors interfere in different ways with pentylenetetrazole seizures, kindling, and kindling-related learning deficits. Naunyn-Schmiedeberg's archives of pharmacology 20040701
Desensitization and internalization of metabotropic glutamate receptor 1a following activation of heterologous Gq/11-coupled receptors. Biochemistry 20040615
Agonist-independent internalization of metabotropic glutamate receptor 1a is arrestin- and clathrin-dependent and is suppressed by receptor inverse agonists. Journal of neurochemistry 20040501
In vivo modulation of extracellular hippocampal glutamate and GABA levels and limbic seizures by group I and II metabotropic glutamate receptor ligands. Journal of neurochemistry 20040301
Stereoselective synthesis and preliminary evaluation of (+)- and (-)-3-methyl-5-carboxy-thien-2-yl-glycine (3-MATIDA): identification of (+)-3-MATIDA as a novel mGluR1 competitive antagonist. Farmaco (Societa chimica italiana : 1989) 20040201
Blockade of excitatory amino acid transporters in the rat hippocampus results in enhanced activation of group I and group III metabotropic glutamate receptors. Neuropharmacology 20031201
Contribution of spinal glutamatergic mechanisms in heterosegmental antinociception induced by noxious stimulation. Pain 20031101
Changes of metabotropic glutamate receptor subtype 1a in diffuse brain injury with secondary brain insults and the effects of 2-methyl-4-carboxyphenylglycine. Chinese journal of traumatology = Zhonghua chuang shang za zhi 20031001
Associative mossy fibre LTP induced by pairing presynaptic stimulation with postsynaptic hyperpolarization of CA3 neurons in rat hippocampal slice. The European journal of neuroscience 20030401
Optical imaging of long-term depression in the mouse cerebellar cortex in vivo. The Journal of neuroscience : the official journal of the Society for Neuroscience 20030301
Antagonism of glutamatergic metabotropic receptors in the NTS of awake rats does not affect the gain of the baroreflex. Autonomic neuroscience : basic & clinical 20030131
Corticostriatal LTP requires combined mGluR1 and mGluR5 activation. Neuropharmacology 20030101
Actions of Group I and Group II metabotropic glutamate receptor ligands on 5-hydroxytryptamine release in the rat cerebral cortex in vivo: differential roles in the regulation of central serotonergic neurotransmission. Neuroscience 20030101
Role of synaptic metabotropic glutamate receptors in epileptiform discharges in hippocampal slices. Journal of neurophysiology 20021001
Inhibition of group I metabotropic glutamate receptor responses in vivo in rats by a new generation of carboxyphenylglycine-like amino acid antagonists. Neuroscience letters 20020920
Group I metabotropic glutamate receptor-mediated enhancement of dopamine cell burst firing in rat ventral tegmental area in vitro. Brain research 20020906
Activation of glutamate receptors inhibits Na/K-ATPase of cerebellum granule cells. Biochemistry. Biokhimiia 20020901
Metabotropic glutamate receptors in the hippocampus and nucleus accumbens are involved in generating seizure-induced hippocampal gamma waves and behavioral hyperactivity. Behavioural brain research 20020615
Metabotropic glutamate receptors mediate expression of LTP in slices of rat visual cortex. The European journal of neuroscience 20020501
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
Completing the corticofugal loop: a visual role for the corticogeniculate type 1 metabotropic glutamate receptor. The Journal of neuroscience : the official journal of the Society for Neuroscience 20020401
Group II metabotropic glutamate receptor activation is required for normal hippocampal mossy fibre development in the rat. The Journal of physiology 20020215
In vivo effects of intracortical administration of NMDA and metabotropic glutamate receptors antagonists on neocortical long-term potentiation and conditioned taste aversion. Behavioural brain research 20020201
Activation of metabotropic glutamate receptor mediates upregulation of transcription factor mRNA expression in rat striatum induced by acute administration of amphetamine. Brain research 20020111
Group I metabotropic glutamate receptor antagonists block secondary thermal hyperalgesia in rats with knee joint inflammation. The Journal of pharmacology and experimental therapeutics 20020101
Differential roles for mGluR1 and mGluR5 in the persistent prolongation of epileptiform bursts. Journal of neurophysiology 20020101
Group I metabotropic glutamate receptors in spinal cord injury: roles in neuroprotection and the development of chronic central pain. Journal of neurotrauma 20020101
Characterization of an N-terminal secreted domain of the type-1 human metabotropic glutamate receptor produced by a mammalian cell line. Journal of neurochemistry 20020101
Visualization of IP(3) dynamics reveals a novel AMPA receptor-triggered IP(3) production pathway mediated by voltage-dependent Ca(2+) influx in Purkinje cells. Neuron 20011011
Endogenous activation of group-I metabotropic glutamate receptors is required for differentiation and survival of cerebellar Purkinje cells. The Journal of neuroscience : the official journal of the Society for Neuroscience 20011001
Presynaptic modulation by group III metabotropic glutamate receptors (mGluRs) of the excitatory postsynaptic potential mediated by mGluR1 in rat cerebellar Purkinje cells. Neuroscience letters 20010907
Differential roles for glutamate receptor subtypes within commissural NTS in cardiac-sympathetic reflex. American journal of physiology. Regulatory, integrative and comparative physiology 20010901
Glutamate receptor stimulation induces a persistent rhythmicity of the GABAergic inputs to rat midbrain dopaminergic neurons. The European journal of neuroscience 20010901
Neuronal glutamate transporters control activation of postsynaptic metabotropic glutamate receptors and influence cerebellar long-term depression. Neuron 20010830
Neuroprotection afforded by NAAG and NAALADase inhibition requires glial cells and metabotropic glutamate receptor activation. European journal of pharmacology 20010824
Metabotropic glutamate receptors 1 and 5 differentially regulate CA1 pyramidal cell function. The Journal of neuroscience : the official journal of the Society for Neuroscience 20010815
Changes in rat serum corticosterone after treatment with metabotropic glutamate receptor agonists or antagonists. Journal of neuroendocrinology 20010801
Group I metabotropic glutamate receptors limit AMPA receptor-mediated oligodendrocyte progenitor cell death. European journal of pharmacology 20010727
Synthesis of N(1)-substituted analogues of (2R,4R)-4-amino-pyrrolidine-2,4-dicarboxylic acid as agonists, partial agonists, and antagonists of group II metabotropic glutamate receptors. Bioorganic & medicinal chemistry letters 20010723
A metabotropic glutamate receptor antagonist, alpha-methyl-4-carboxyphenylglycine, attenuates immediate early gene mRNA expression following traumatic injury in cultured rat cortical glial cells. Neuroscience letters 20010622
Selective involvement of mGlu1 receptors in corticostriatal LTD. Neuropharmacology 20010601
Properties of synchronous and asynchronous release during pulse train depression in cultured hippocampal neurons. Journal of neurophysiology 20010601
A kainate receptor increases the efficacy of GABAergic synapses. Neuron 20010501
Synthesis of phenylglycine derivatives as potent and selective antagonists of group III metabotropic glutamate receptors. Bioorganic & medicinal chemistry letters 20010326
Activation of metabotropic glutamate receptors induces gamma frequency oscillations in the rat dentate gyrus in vivo. Neuropharmacology 20010301
Task-dependent role for dorsal striatum metabotropic glutamate receptors in memory. Learning & memory (Cold Spring Harbor, N.Y.) 20010301
Selective blockade of the mGluR1 receptor reduces traumatic neuronal injury in vitro and improvesoOutcome after brain trauma. Experimental neurology 20010201
Temperature-dependent separation of a delayed-onset long-lasting enhancement mediated by coactivation of NMDA and metabotropic glutamate receptors following a transient exposure of extracellular high Ca(2+). Neuroscience 20010101
Group II metabotropic glutamate receptor activation protects striatal dopaminergic nerve terminals against MPP+-induced neurotoxicity along with brain-derived neurotrophic factor induction. Journal of neurochemistry 20010101
Stimulation of metabotropic but not ionotropic glutamatergic receptors in the nucleus accumbens is required for the D-amphetamine-induced release of functional dopamine. Neuroscience 20010101
Metabotropic glutamate receptor 5 mediates the potentiation of N-methyl-D-aspartate responses in medium spiny striatal neurons. Neuroscience 20010101
Effects of blockade of metabotropic glutamate receptors in the subthalamic nucleus on haloperidol-induced Parkinsonism in rats. Neuroscience letters 20000317
Synthesis and pharmacological characterization of all sixteen stereoisomers of 2-(2'-carboxy-3'-phenylcyclopropyl)glycine. Focus on (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-phenylcyclopropyl)glycine, a novel and selective group II metabotropic glutamate receptors antagonist. Journal of medicinal chemistry 19960524
Pharmacological analysis of 4-carboxyphenylglycine derivatives: comparison of effects on mGluR1 alpha and mGluR5a subtypes. Neuropharmacology 19950801
Properties