Home Other Building Blocks (AR,BS)-ALPHA-(4-HYDROXYPHENYL)-BETA-METHYL-4-(PHENYLMETHYL)-1-PIPERIDINEPROPANOL MALEATE

(AR,BS)-ALPHA-(4-HYDROXYPHENYL)-BETA-METHYL-4-(PHENYLMETHYL)-1-PIPERIDINEPROPANOL MALEATE

CAS No.:
169274-78-6
Catalog Number:
AG00ABLL
Molecular Formula:
C22H29NO2
Molecular Weight:
339.4712
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Purity
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Product Description
Catalog Number:
AG00ABLL
Chemical Name:
(AR,BS)-ALPHA-(4-HYDROXYPHENYL)-BETA-METHYL-4-(PHENYLMETHYL)-1-PIPERIDINEPROPANOL MALEATE
CAS Number:
169274-78-6
Molecular Formula:
C22H29NO2
Molecular Weight:
339.4712
MDL Number:
MFCD06798375
IUPAC Name:
4-[(1R,2S)-3-(4-benzylpiperidin-1-yl)-1-hydroxy-2-methylpropyl]phenol
InChI:
InChI=1S/C22H29NO2/c1-17(22(25)20-7-9-21(24)10-8-20)16-23-13-11-19(12-14-23)15-18-5-3-2-4-6-18/h2-10,17,19,22,24-25H,11-16H2,1H3/t17-,22+/m0/s1
InChI Key:
WVZSEUPGUDIELE-HTAPYJJXSA-N
SMILES:
C[C@H]([C@H](c1ccc(cc1)O)O)CN1CCC(CC1)Cc1ccccc1
Properties
Complexity:
366  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
339.22g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
339.479g/mol
Monoisotopic Mass:
339.22g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
43.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.2  
Literature
Title Journal
Effect of oestrogen receptors on brain NMDA receptors of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine mice. Journal of neuroendocrinology 20121101
Ifenprodil, a NR2B-selective antagonist of NMDA receptor, inhibits reverse Na+/Ca2+ exchanger in neurons. Neuropharmacology 20121101
Involvement of the anterior cingulate cortex in formation, consolidation, and reconsolidation of recent and remote contextual fear memory. Learning & memory (Cold Spring Harbor, N.Y.) 20120914
NMDARs mediate the role of monoamine oxidase A in pathological aggression. The Journal of neuroscience : the official journal of the Society for Neuroscience 20120620
NMDA receptor mediated phosphorylation of GluR1 subunits contributes to the appearance of calcium-permeable AMPA receptors after mechanical stretch injury. Neurobiology of disease 20120601
Investigation of the antidyskinetic site of action of metabotropic and ionotropic glutamate receptor antagonists. Intracerebral infusions in 6-hydroxydopamine-lesioned rats with levodopa-induced dyskinesia. European journal of pharmacology 20120515
Hippocampus versus entorhinal cortex decoupling by an NR2 subunit-specific block of NMDA receptors in a rat in vitro model of temporal lobe epilepsy. Epilepsia 20120501
Reduction of inflammatory pain in female rats after NR2B NMDA cortical antagonism. Psicothema 20120501
Effect of NMDA NR2B antagonist on neuropathic pain in two spinal cord injury models. Pain 20120501
Role of GluN2A and GluN2B subunits in the formation of filopodia and secondary dendrites in cultured hippocampal neurons. Naunyn-Schmiedeberg's archives of pharmacology 20120201
Isoflurane/nitrous oxide anesthesia induces increases in NMDA receptor subunit NR2B protein expression in the aged rat brain. Brain research 20120111
Inhibition of Ca2+/calmodulin-dependent protein kinase II reverses oxaliplatin-induced mechanical allodynia in rats. Molecular pain 20120101
Genetic, pharmacological and lesion analyses reveal a selective role for corticohippocampal GLUN2B in a novel repeated swim stress paradigm. Neuroscience 20111013
Neuronal NR2B-containing NMDA receptor mediates spinal astrocytic c-Jun N-terminal kinase activation in a rat model of neuropathic pain. Brain, behavior, and immunity 20111001
Blockade of NMDA receptors 2A subunit in the dorsal striatum impairs the learning of a complex motor skill. Behavioral neuroscience 20111001
Kalirin binds the NR2B subunit of the NMDA receptor, altering its synaptic localization and function. The Journal of neuroscience : the official journal of the Society for Neuroscience 20110831
Blockade of NMDA GluN2B receptors selectively impairs behavioral flexibility but not initial discrimination learning. Psychopharmacology 20110801
Involvement of synaptic NR2B-containing NMDA receptors in long-term depression induction in the young rat visual cortex in vitro. The Chinese journal of physiology 20110630
Peripheral administration of NR2 antagonists attenuates orofacial formalin-induced nociceptive behavior in rats. Progress in neuro-psychopharmacology & biological psychiatry 20110601
A silent synapse-based mechanism for cocaine-induced locomotor sensitization. The Journal of neuroscience : the official journal of the Society for Neuroscience 20110601
Dopamine induces a GluN2A-dependent form of long-term depression of NMDA synaptic responses in the nucleus accumbens. Neuropharmacology 20110501
Therapeutic significance of NR2B-containing NMDA receptors and mGluR5 metabotropic glutamate receptors in mediating the synaptotoxic effects of β-amyloid oligomers on long-term potentiation (LTP) in murine hippocampal slices. Neuropharmacology 20110501
NR2B subunit blockade does not affect motor symptoms induced by 3-nitropropionic acid. Neurological research 20110501
Glutamate N-methyl-D-aspartate receptor antagonists rapidly reverse behavioral and synaptic deficits caused by chronic stress exposure. Biological psychiatry 20110415
The effects of NMDA receptor antagonists on attentional set-shifting task performance in mice. Psychopharmacology 20110401
NR2B subunit-specific NMDA antagonist Ro25-6981 inhibits the expression of conditioned fear: a comparison with the NMDA antagonist MK-801 and fluoxetine. Behavioural pharmacology 20110401
Nickel modulates the electrical activity of cultured cortical neurons through a specific effect on N-methyl-D-aspartate receptor channels. Neuroscience 20110317
Cyclic adenosine monophosphate-independent tyrosine phosphorylation of NR2B mediates cocaine-induced extracellular signal-regulated kinase activation. Biological psychiatry 20110201
[Effects of the neurogenesis stimulator Ro 25-6981 upon formation of spatial skill in adult rats depend on the term of its administration and the animals' ability to learn]. Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20110201
An examination of NMDA receptor contribution to conditioned responding evoked by the conditional stimulus effects of nicotine. Psychopharmacology 20110101
Involvement of spinal NR2B-containing NMDA receptors in oxaliplatin-induced mechanical allodynia in rats. Molecular pain 20110101
Intracisternal administration of NR2 subunit antagonists attenuates the nociceptive behavior and p-p38 MAPK expression produced by compression of the trigeminal nerve root. Molecular pain 20110101
Lack of efficacy of NMDA receptor-NR2B selective antagonists in the R6/2 model of Huntington disease. Experimental neurology 20101001
Identification of a novel NR2B-selective NMDA receptor antagonist using a virtual screening approach. Bioorganic & medicinal chemistry letters 20100915
mTOR-dependent synapse formation underlies the rapid antidepressant effects of NMDA antagonists. Science (New York, N.Y.) 20100820
Long-lasting adaptations of the NR2B-containing NMDA receptors in the dorsomedial striatum play a crucial role in alcohol consumption and relapse. The Journal of neuroscience : the official journal of the Society for Neuroscience 20100728
Inverse relationship between seizure expression and extrasynaptic NMDAR function following chronic NMDAR inhibition. Epilepsia 20100701
Stoichiometry of N-methyl-D-aspartate receptors within the suprachiasmatic nucleus. Journal of neurophysiology 20100601
Contribution of the spinal cord BDNF to the development of neuropathic pain by activation of the NR2B-containing NMDA receptors in rats with spinal nerve ligation. Experimental neurology 20100401
Effects of agents targeting glutamatergic systems on marble-burying behavior. Neuroscience letters 20100303
NMDA NR2B subtype-selective receptor antagonists fail to antagonize electrically-precipitated seizures and elicit popping in mice. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20100301
Effects of acute stress and GluN2B-containing NMDA receptor antagonism on object and object-place recognition memory. Neurobiology of learning and memory 20100201
Intracisternal administration of NR2 antagonists attenuates facial formalin-induced nociceptive behavior in rats. Journal of orofacial pain 20100101
Postsynaptic response to stimulation of the Schaffer collaterals with properties similar to those of synaptosomal aspartate release. Brain research 20091027
NR2A-containing NMDA receptors are required for L-LTP induction and depotentiation in CA1 region of hippocampal slices. The European journal of neuroscience 20090601
A novel protein complex in membrane rafts linking the NR2B glutamate receptor and autophagy is disrupted following traumatic brain injury. Journal of neurotrauma 20090501
Platelet-derived growth factor selectively inhibits NR2B-containing N-methyl-D-aspartate receptors in CA1 hippocampal neurons. The Journal of biological chemistry 20090320
Late phase of long-term potentiation induced by co-application of N-methyl-d-aspartic acid and the antagonist of NR2B-containing N-methyl-d-aspartic acid receptors in rat hippocampus. Neuroscience 20090303
Development of 3-substituted-1H-indole derivatives as NR2B/NMDA receptor antagonists. Bioorganic & medicinal chemistry 20090215
Role of the spinal cord NR2B-containing NMDA receptors in the development of neuropathic pain. Experimental neurology 20090201
Fear memory impairing effects of systemic treatment with the NMDA NR2B subunit antagonist, Ro 25-6981, in mice: attenuation with ageing. Pharmacology, biochemistry, and behavior 20090101
A role of periaqueductal grey NR2B-containing NMDA receptor in mediating persistent inflammatory pain. Molecular pain 20090101
D1/5 receptor-mediated enhancement of LTP requires PKA, Src family kinases, and NR2B-containing NMDARs. Neuropharmacology 20081001
Differential effect of NR2A and NR2B subunit selective NMDA receptor antagonists on striato-pallidal neurons: relationship to motor response in the 6-hydroxydopamine model of parkinsonism. Journal of neurochemistry 20080701
Cerebellar granule cells cultured from adolescent rats express functional NMDA receptors: an in vitro model for studying the developing cerebellum. Journal of neurochemistry 20080701
D-serine augments NMDA-NR2B receptor-dependent hippocampal long-term depression and spatial reversal learning. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20080401
Spinal cord long-term potentiation is attenuated by the NMDA-2B receptor antagonist Ro 25-6981. Acta physiologica (Oxford, England) 20080301
Tonic facilitation of glutamate release by glycine binding sites on presynaptic NR2B-containing NMDA autoreceptors in the rat visual cortex. Neuroscience letters 20080227
Intrathecal high-dose histamine induces spinally-mediated nociceptive behavioral responses through a polyamine site of NMDA receptors. European journal of pharmacology 20080226
Brain-derived neurotrophic factor activation of extracellular signal-regulated kinase is autonomous from the dominant extrasynaptic NMDA receptor extracellular signal-regulated kinase shutoff pathway. Neuroscience 20080124
Effects of pan- and subtype-selective N-methyl-D-aspartate receptor antagonists on cortical spreading depression in the rat: therapeutic potential for migraine. The Journal of pharmacology and experimental therapeutics 20070501
Selective NR1/2B N-methyl-D-aspartate receptor antagonists among indole-2-carboxamides and benzimidazole-2-carboxamides. Journal of medicinal chemistry 20070308
Contribution of NMDA receptor NR2B subunit to synaptic plasticity during associative learning in behaving rats. The European journal of neuroscience 20070201
Activation of NR2B-containing NMDA receptors is not required for NMDA receptor-dependent long-term depression. Neuropharmacology 20070101
Differential roles of NR2A and NR2B-containing NMDA receptors in LTP and LTD in the CA1 region of two-week old rat hippocampus. Neuropharmacology 20070101
NR2B antagonists restrict spatiotemporal spread of activity in a rat model of cortical dysplasia. Epilepsy research 20061201
N-methyl-D-aspartate receptor-dependent long-term potentiation in CA1 region affects synaptic expression of glutamate receptor subunits and associated proteins in the whole hippocampus. Neuroscience 20060901
Benzimidazole-2-carboxamides as novel NR2B selective NMDA receptor antagonists. Bioorganic & medicinal chemistry letters 20060901
NR2B-containing N-methyl-D-aspartate subtype glutamate receptors regulate the acute stress effect on hippocampal long-term potentiation/long-term depression in vivo. Neuroreport 20060821
Estradiol-induced increase in the magnitude of long-term potentiation is prevented by blocking NR2B-containing receptors. The Journal of neuroscience : the official journal of the Society for Neuroscience 20060816
An animal model of chronic inflammatory pain: pharmacological and temporal differentiation from acute models. European journal of pain (London, England) 20060801
Effects of N-methyl-D-aspartate receptor antagonism on neuroleptic-induced orofacial dyskinesias. Psychopharmacology 20060401
Developmental changes in NMDA neurotoxicity reflect developmental changes in subunit composition of NMDA receptors. The Journal of neuroscience : the official journal of the Society for Neuroscience 20060315
Glutamate-based therapeutic approaches: NR2B receptor antagonists. Current opinion in pharmacology 20060201
Novel blockade of protein kinase A-mediated phosphorylation of AMPA receptors. The Journal of neuroscience : the official journal of the Society for Neuroscience 20060125
Tonic facilitation of glutamate release by presynaptic NR2B-containing NMDA receptors is increased in the entorhinal cortex of chronically epileptic rats. The Journal of neuroscience : the official journal of the Society for Neuroscience 20060111
Role of neuronal NR2B subunit-containing NMDA receptor-mediated Ca2+ influx and astrocytic activation in cultured mouse cortical neurons and astrocytes. Synapse (New York, N.Y.) 20060101
Contribution of NR2A and NR2B NMDA subunits to bidirectional synaptic plasticity in the hippocampus in vivo. Hippocampus 20060101
Stress evoked by opiate withdrawal facilitates hippocampal LTP in vivo. Hippocampus 20060101
Roles of NMDA NR2B subtype receptor in prefrontal long-term potentiation and contextual fear memory. Neuron 20050915
Functional roles of NMDA receptor NR2A and NR2B subunits in the acute intoxicating effects of ethanol in mice. Synapse (New York, N.Y.) 20050615
Selective subunit antagonists suggest an inhibitory relationship between NR2B and NR2A-subunit containing N-methyl-D: -aspartate receptors in hippocampal slices. Experimental brain research 20050401
BDNF enhancement of postsynaptic NMDA receptors is blocked by ethanol. Synapse (New York, N.Y.) 20050101
The NR2B-selective N-methyl-D-aspartate receptor antagonist Ro 25-6981 [(+/-)-(R*,S*)-alpha-(4-hydroxyphenyl)-beta-methyl-4-(phenylmethyl)-1-piperidine propanol] potentiates the effect of nicotine on locomotor activity and dopamine release in the nucleus accumbens. The Journal of pharmacology and experimental therapeutics 20041101
Differential roles of NR2A and NR2B-containing NMDA receptors in cortical long-term potentiation and long-term depression. The Journal of neuroscience : the official journal of the Society for Neuroscience 20040908
Oxamides as novel NR2B selective NMDA receptor antagonists. Bioorganic & medicinal chemistry letters 20040802
Modulation of morphine analgesia by site-specific N-methyl-D-aspartate receptor antagonists: dependence on sex, site of antagonism, morphine dose, and time. Pain 20040601
Role of NMDA receptor subtypes in governing the direction of hippocampal synaptic plasticity. Science (New York, N.Y.) 20040514
Antiparkinsonian activity of Ro 25-6981, a NR2B subunit specific NMDA receptor antagonist, in animal models of Parkinson's disease. Experimental neurology 20040501
The NMDA receptor NR2B subunit: a valid therapeutic target for multiple CNS pathologies. Current medicinal chemistry 20040201
Identification of critical residues in the amino terminal domain of the human NR2B subunit involved in the RO 25-6981 binding pocket. The Journal of pharmacology and experimental therapeutics 20031201
Indole-2-carboxamides as novel NR2B selective NMDA receptor antagonists. Bioorganic & medicinal chemistry letters 20031103
Asymmetrical allocation of NMDA receptor epsilon2 subunits in hippocampal circuitry. Science (New York, N.Y.) 20030509
Role of the NMDA receptor NR2B subunit in the discriminative stimulus effects of ketamine. Behavioural pharmacology 20030501
2-(3,4-Dihydro-1H-isoquinolin-2yl)-pyridines as a novel class of NR1/2B subtype selective NMDA receptor antagonists. Bioorganic & medicinal chemistry letters 20030310
Novel N1-(benzyl)cinnamamidine derived NR2B subtype-selective NMDA receptor antagonists. Bioorganic & medicinal chemistry letters 20030224
The NMDA receptor NR2B subtype selective antagonist Ro 25-6981 aggravates paroxysmal dyskinesia in the dt(sz) mutant. European journal of pharmacology 20030101
Blockade of NMDA receptor subtype NR2B prevents seizures but not apoptosis of dentate gyrus neurons in bacterial meningitis in infant rats. BMC neuroscience 20030101
Role of NR2B-containing N-methyl-D-aspartate receptors in haloperidol-induced c-Fos expression in the striatum and nucleus accumbens. Neuroscience 20030101
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
Discovery of (R)-1-[2-hydroxy-3-(4-hydroxy-phenyl)-propyl]-4-(4-methyl-benzyl)-piperidin-4-ol: a novel NR1/2B subtype selective NMDA receptor antagonist. Bioorganic & medicinal chemistry letters 20010820
Estrogen-like activity of tamoxifen and raloxifene on NMDA receptor binding and expression of its subunits in rat brain. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20010801
NMDA receptor antagonists do not block the development of sensitization of catalepsy, but make its expression state-dependent. Behavioural pharmacology 20010401
Pharmacological characterization of interactions of RO 25-6981 with the NR2B (epsilon2) subunit. European journal of pharmacology 20010330
Properties