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Description: Potent NMDA antagonist; more active enantiomer of (RS)-CPP
Chemical Name: 3-((R)-2-Carboxypiperazin-4-yl)-propyl-1-phosphonic acid
Biological Activity for (R)-CPP
(R)-CPP is a highly potent NMDA antagonist; more active isomer. Shows some selectivity for GluN2A (formally NR2A) containing receptors (Ki values are 0.041, 0.27, 0.63 and 1.99 μM for inhibition of GluN2A-, GluN2B-, GluN2C- and GluN2D-containing recombinant NMDA receptors respectively).
Racemate also available.
Please refer to IUPHAR Guide to Pharmacology for the most recent naming conventions.
Technical Data for (R)-CPP
| M. Wt | 252.21 |
| Formula | C8H17N2O5P |
| Storage | Desiccate at RT |
| CAS Number | 126453-07-4 |
| PubChem ID | 6603754 |
| InChI Key | CUVGUPIVTLGRGI-SSDOTTSWSA-N |
| Smiles | [H][C@@]1([C@](O)=O)NCCN(CCCP(O)(O)=O)C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for (R)-CPP
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 25.22 | 100 |
Preparing Stock Solutions for (R)-CPP
The following data is based on the product molecular weight 252.21. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 3.96 mL | 19.82 mL | 39.65 mL |
| 5 mM | 0.79 mL | 3.96 mL | 7.93 mL |
| 10 mM | 0.4 mL | 1.98 mL | 3.96 mL |
| 50 mM | 0.08 mL | 0.4 mL | 0.79 mL |
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Product Datasheets for (R)-CPP
References for (R)-CPP
References are publications that support the biological activity of the product.
Feng et al (2004) Structure-activity analysis of a novel NR2C/NR2D-preferring NMDA receptor antagonist: 1-(phenanthrene-2-carbonyl) piperazine-2,3-dicarboxylic acid. Br.J.Pharmacol. 141 508 PMID: 14718249
Aebischer et al (1989) Synthesis and NMDA antagonistic properties of the enantiomers of 4-(3-phosphonopropyl)piperazine-2-carboxylic acid (CPP) and of the unsaturated analogue (E)-4-(3-phosphono-2-enyl)piperazine-2-carboxylic acid (CPP-ene). Helv.Chim.Acta 72 1043
If you know of a relevant reference for (R)-CPP, please let us know.
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Keywords: (R)-CPP, (R)-CPP supplier, Potent, NMDA, antagonists, Glutamate, Receptors, N-Methyl-D-Aspartate, iGluR, Ionotropic, 0247, Tocris Bioscience
14 Citations for (R)-CPP
Citations are publications that use Tocris products. Selected citations for (R)-CPP include:
Zhang et al (2018) Heparan Sulfate Organizes Neuronal Synapses through Neurexin Partnerships. Cell 174 1450 PMID: 30100184
Stephany et al (2014) Plasticity of binocularity and visual acuity are differentially limited by nogo receptor. PLoS One 34 11631 PMID: 25164659
Vigot et al (2006) Differential compartmentalization and distinct functions of GABAB receptor variants. Neuron 50 589 PMID: 16701209
Chaffiol et al (2017) A New Promoter Allows Optogenetic Vision Restoration with Enhanced Sensitivity in Macaque Retina. Mol Ther 25 2546 PMID: 28807567
Tsutsui-Kimura et al (2015) Milnacipran remediates impulsive deficits in rats with lesions of the ventromedial prefrontal cortex. J Neurosci 18 PMID: 25522418
Wood et al (2009) Synaptic circuit abnormalities of motor-frontal layer 2/3 pyramidal neurons in an RNA interference model of methyl-CpG-binding protein 2 deficiency. Int J Neuropsychopharmacol 29 12440 PMID: 19812320
Mao et al Characterization and subcellular targeting of GCaMP-type genetically-encoded calcium indicators. Nat Commun 3 e1796 PMID: 18350138
Pan et al (2016) Neuronal firing patterns outweigh circuitry oscillations in parkinsonian motor control. J Clin Invest 126 4516 PMID: 27797341
Maeder et al (2018) The THO Complex Coordinates Transcripts for Synapse Development and DA Neuron Survival. Cell 174 1436 PMID: 30146163
Sancho and Bloodgood (2018) Functional Distinctions between Spine and Dendritic Synapses Made onto Parvalbumin-Positive Interneurons in Mouse Cortex. Cell Rep 24 2075 PMID: 30134169
Collins et al (2018) Reciprocal Circuits Linking the Prefrontal Cortex with Dorsal and Ventral Thalamic Nuclei. Neuron 98 366 PMID: 29628187
Fan et al (2018) All-optical synaptic electrophysiology probes mechanism of ketamine-induced disinhibition. Nat Methods 15 823 PMID: 30275587
Chang and Higley (2018) Potassium channels contribute to activity-dependent regulation of dendritic inhibition. Physiol Rep 6 e13747 PMID: 29939492
Higley et al (2011) Cholinergic interneurons mediate fast VGluT3-dependent glutamatergic transmission in the striatum. PLoS One 6 e19155 PMID: 21544206
Do you know of a great paper that uses (R)-CPP from Tocris? Please let us know.
Reviews for (R)-CPP
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CPP action on human neutrophils.
By
Anonymous on 07/13/2023
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: Blood
(R)-CPP was used to quantify the input of Ca2+ flow through NMDA receptors into Ca2+ concentration fluctuations in human neutrophils. Figure: impact of (R)-CPP on Ca2+ - induced fluorescence in cultured neutrophils (+CPP bar).
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