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134234-12-1,MFCD00926469
Catalog No.:AA007MDB

134234-12-1 | 1-((1S,2S)-1-Hydroxy-1-(4-hydroxyphenyl)propan-2-yl)-4-phenylpiperidin-4-ol

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1mg
98%
in stock  
$41.00   $29.00
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5mg
≥98%
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$103.00   $72.00
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10mg
≥98%
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$133.00   $93.00
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25mg
≥98%
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$305.00   $213.00
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50mg
98% (HPLC)
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100mg
98% (HPLC)
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA007MDB
Chemical Name:
1-((1S,2S)-1-Hydroxy-1-(4-hydroxyphenyl)propan-2-yl)-4-phenylpiperidin-4-ol
CAS Number:
134234-12-1
Molecular Formula:
C20H25NO3
Molecular Weight:
327.4174
MDL Number:
MFCD00926469
SMILES:
Oc1ccc(cc1)[C@@H]([C@@H](N1CCC(CC1)(O)c1ccccc1)C)O
Properties
Computed Properties
 
Complexity:
380  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
4  
XLogP3:
2.3  

Downstream Synthesis Route

[1]Chenard;Bordner;Butler;Chambers;Collins;DeCosta;Ducat;Dumont;Fox;Mena;Menniti;Nielsen;Pagnozzi;Richter;Ronau;Shalaby;Stemple;White[JournalofMedicinalChemistry,1995,vol.38,#16,p.3138-3145]

[1]Chenard;Bordner;Butler;Chambers;Collins;DeCosta;Ducat;Dumont;Fox;Mena;Menniti;Nielsen;Pagnozzi;Richter;Ronau;Shalaby;Stemple;White[JournalofMedicinalChemistry,1995,vol.38,#16,p.3138-3145]

[1]Chenard;Bordner;Butler;Chambers;Collins;DeCosta;Ducat;Dumont;Fox;Mena;Menniti;Nielsen;Pagnozzi;Richter;Ronau;Shalaby;Stemple;White[JournalofMedicinalChemistry,1995,vol.38,#16,p.3138-3145]

[1]Chenard;Bordner;Butler;Chambers;Collins;DeCosta;Ducat;Dumont;Fox;Mena;Menniti;Nielsen;Pagnozzi;Richter;Ronau;Shalaby;Stemple;White[JournalofMedicinalChemistry,1995,vol.38,#16,p.3138-3145]

[1]Chenard;Bordner;Butler;Chambers;Collins;DeCosta;Ducat;Dumont;Fox;Mena;Menniti;Nielsen;Pagnozzi;Richter;Ronau;Shalaby;Stemple;White[JournalofMedicinalChemistry,1995,vol.38,#16,p.3138-3145]

Literature

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Journal: Toxicology and applied pharmacology 20171101

Title: Traxoprodil decreases pentylenetetrazol-induced seizures.

Journal: Epilepsy research 20120601

Title: Effects of NMDA receptor antagonists with different subtype selectivities on retinal spreading depression.

Journal: British journal of pharmacology 20120101

Title: Behavioral deficits and cellular damage following developmental ethanol exposure in rats are attenuated by CP-101,606, an NMDAR antagonist with unique NR2B specificity.

Journal: Pharmacology, biochemistry, and behavior 20120101

Title: A complex interaction between glycine/NMDA receptors and serotonergic/noradrenergic antidepressants in the forced swim test in mice.

Journal: Journal of neural transmission (Vienna, Austria : 1996) 20111101

Title: A role for glutamate in subjective response to smoking and its action on inhibitory control.

Journal: Psychopharmacology 20110701

Title: Nonselective and NR2B-selective N-methyl-D-aspartic acid receptor antagonists produce antinociception and long-term relief of allodynia in acute and neuropathic pain.

Journal: Anesthesiology 20110701

Title: 2,6-Disubstituted pyrazines and related analogs as NR2B site antagonists of the NMDA receptor with anti-depressant activity.

Journal: Bioorganic & medicinal chemistry letters 20110601

Title: The effects of NMDA receptor antagonists on attentional set-shifting task performance in mice.

Journal: Psychopharmacology 20110401

Title: Triheteromeric NR1/NR2A/NR2B receptors constitute the major N-methyl-D-aspartate receptor population in adult hippocampal synapses.

Journal: The Journal of biological chemistry 20110304

Title: Involvement of spinal NR2B-containing NMDA receptors in oxaliplatin-induced mechanical allodynia in rats.

Journal: Molecular pain 20110101

Title: Lack of efficacy of NMDA receptor-NR2B selective antagonists in the R6/2 model of Huntington disease.

Journal: Experimental neurology 20101001

Title: Forelimb dyskinesia mediated by high-frequency stimulation of the subthalamic nucleus is linked to rapid activation of the NR2B subunit of N-methyl-D-aspartate receptors.

Journal: The European journal of neuroscience 20100801

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Journal: Indian journal of psychiatry 20100101

Title: Glutamate-based antidepressants: 20 years on.

Journal: Trends in pharmacological sciences 20091101

Title: Comments on 'An innovative design to establish proof of concept of the antidepressant effects of the NR2B subunit selective N-methyl-D-aspartate antagonist, CP-101,606 in patients with treatment-refractory major depressive disorder'.

Journal: Journal of clinical psychopharmacology 20090801

Title: An innovative design to establish proof of concept of the antidepressant effects of the NR2B subunit selective N-methyl-D-aspartate antagonist, CP-101,606, in patients with treatment-refractory major depressive disorder.

Journal: Journal of clinical psychopharmacology 20081201

Title: Effects of a NR2B selective NMDA glutamate antagonist, CP-101,606, on dyskinesia and Parkinsonism.

Journal: Movement disorders : official journal of the Movement Disorder Society 20081015

Title: Amygdala infusions of an NR2B-selective or an NR2A-preferring NMDA receptor antagonist differentially influence fear conditioning and expression in the fear-potentiated startle test.

Journal: Learning & memory (Cold Spring Harbor, N.Y.) 20080201

Title: The phencyclidine-like discriminative stimulus effects and reinforcing properties of the NR2B-selective N-methyl-D-aspartate antagonist CP-101 606 in rats and rhesus monkeys.

Journal: Behavioural pharmacology 20071201

Title: Discovery of (-)-6-[2-[4-(3-fluorophenyl)-4-hydroxy-1-piperidinyl]-1-hydroxyethyl]-3,4-dihydro-2(1H)-quinolinone--a potent NR2B-selective N-methyl D-aspartate (NMDA) antagonist for the treatment of pain.

Journal: Bioorganic & medicinal chemistry letters 20071015

Title: Metabolism, distribution and excretion of a selective N-methyl-D-aspartate receptor antagonist, traxoprodil, in rats and dogs.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20070801

Title: Nitric oxide (NO) serves as a retrograde messenger to activate neuronal NO synthase in the spinal cord via NMDA receptors.

Journal: Nitric oxide : biology and chemistry 20070801

Title: Effects of pan- and subtype-selective N-methyl-D-aspartate receptor antagonists on cortical spreading depression in the rat: therapeutic potential for migraine.

Journal: The Journal of pharmacology and experimental therapeutics 20070501

Title: Selective NR1/2B N-methyl-D-aspartate receptor antagonists among indole-2-carboxamides and benzimidazole-2-carboxamides.

Journal: Journal of medicinal chemistry 20070308

Title: Arthritis and pain. Future targets to control osteoarthritis pain.

Journal: Arthritis research & therapy 20070101

Title: NR2B subunit exerts a critical role in postischemic synaptic plasticity.

Journal: Stroke 20060701

Title: Glutamate-based therapeutic approaches: NR2B receptor antagonists.

Journal: Current opinion in pharmacology 20060201

Title: Absolute oral bioavailability of traxoprodil in cytochrome P450 2D6 extensive and poor metabolisers.

Journal: Clinical pharmacokinetics 20060101

Title: The effect of the selective NMDA receptor antagonist traxoprodil in the treatment of traumatic brain injury.

Journal: Journal of neurotrauma 20051201

Title: Fyn kinase-mediated phosphorylation of NMDA receptor NR2B subunit at Tyr1472 is essential for maintenance of neuropathic pain.

Journal: The European journal of neuroscience 20050901

Title: Lack of NMDA receptor subtype selectivity for hippocampal long-term potentiation.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050720

Title: Evidence for improved performance in cognitive tasks following selective NR2B NMDA receptor antagonist pre-treatment in the rat.

Journal: Psychopharmacology 20050401

Title: NMDA/NR2B selective antagonists in the treatment of ischemic brain injury.

Journal: Current drug targets. CNS and neurological disorders 20050401

Title: Brain but not spinal NR2B receptor is responsible for the anti-allodynic effect of an NR2B subunit-selective antagonist CP-101,606 in a rat chronic constriction injury model.

Journal: Pharmacology 20050101

Title: Characterization of N-methyl-D-aspartate receptor subunits responsible for postoperative pain.

Journal: European journal of pharmacology 20041025

Title: Oxamides as novel NR2B selective NMDA receptor antagonists.

Journal: Bioorganic & medicinal chemistry letters 20040802

Title: NR2B selective NMDA receptor antagonist CP-101,606 prevents levodopa-induced motor response alterations in hemi-parkinsonian rats.

Journal: Neuropharmacology 20040801

Title: The NR2B-selective NMDA receptor antagonist CP-101,606 exacerbates L-DOPA-induced dyskinesia and provides mild potentiation of anti-parkinsonian effects of L-DOPA in the MPTP-lesioned marmoset model of Parkinson's disease.

Journal: Experimental neurology 20040801

Title: Role of NMDA receptor subtypes in the induction of catalepsy and increase in Fos protein expression after administration of haloperidol.

Journal: Brain research 20040611

Title: Synthesis of 11C-labelled bis(phenylalkyl)amines and their in vitro and in vivo binding properties in rodent and monkey brains.

Journal: Biological & pharmaceutical bulletin 20040401

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Journal: Methods and findings in experimental and clinical pharmacology 20040401

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Journal: Current medicinal chemistry 20040201

Title: Characterization of N-methyl-D-aspartate receptor subunits involved in acute ammonia toxicity.

Journal: Neurochemistry international 20040101

Title: The NMDA NR2B subunit-selective receptor antagonist, CP-101,606, enhances the functional recovery the NMDA NR2B subunit-selective receptor and reduces brain damage after cortical compression-induced brain ischemia.

Journal: Journal of neurotrauma 20040101

Title: Antioxidant-accelerated oxidative degradation: a case study of transition metal ion catalyzed oxidation in formulation.

Journal: Pharmaceutical development and technology 20040101

Title: The effect of (+/-)-CP-101,606, an NMDA receptor NR2B subunit selective antagonist, in the Morris watermaze.

Journal: European journal of pharmacology 20030829

Title: 2-(3,4-Dihydro-1H-isoquinolin-2yl)-pyridines as a novel class of NR1/2B subtype selective NMDA receptor antagonists.

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Journal: Bioorganic & medicinal chemistry letters 20030224

Title: Reduced brain infarct volume and improved neurological outcome by inhibition of the NR2B subunit of NMDA receptors by using CP101,606-27 alone and in combination with rt-PA in a thromboembolic stroke model in rats.

Journal: Journal of neurosurgery 20030201

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Journal: Nuclear medicine and biology 20020701

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SDS
Tags:134234-12-1 Molecular Formula|134234-12-1 MDL|134234-12-1 SMILES|134234-12-1 1-((1S,2S)-1-Hydroxy-1-(4-hydroxyphenyl)propan-2-yl)-4-phenylpiperidin-4-ol