(R)-CPP

Pricing Availability   Qty
Description: Potent NMDA antagonist; more active enantiomer of (RS)-CPP
Chemical Name: 3-((R)-2-Carboxypiperazin-4-yl)-propyl-1-phosphonic acid
Datasheet
Citations (15)
Reviews (1)
Literature (5)

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.

Select a batch to recalculate based on the batch molecular weight:
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

Certificate of Analysis / Product Datasheet
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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


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Keywords: (R)-CPP, (R)-CPP supplier, Potent, NMDA, antagonists, Glutamate, Receptors, N-Methyl-D-Aspartate, iGluR, Ionotropic, 0247, Tocris Bioscience

15 Citations for (R)-CPP

Citations are publications that use Tocris products. Selected citations for (R)-CPP include:

Pan et al (2016) Neuronal firing patterns outweigh circuitry oscillations in parkinsonian motor control. J Clin Invest 126 4516 PMID: 27797341

Throesch et al (2024) Functional sensory circuits built from neurons of two species. Cell 187 2143 PMID: 38670072

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

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

Tsutsui-Kimura et al (2015) Milnacipran remediates impulsive deficits in rats with lesions of the ventromedial prefrontal cortex. J Neurosci 18 PMID: 25522418

Higley et al (2011) Cholinergic interneurons mediate fast VGluT3-dependent glutamatergic transmission in the striatum. PLoS One 6 e19155 PMID: 21544206

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

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

Zhang et al (2018) Heparan Sulfate Organizes Neuronal Synapses through Neurexin Partnerships. Cell 174 1450 PMID: 30100184

Chaffiol et al (2017) A New Promoter Allows Optogenetic Vision Restoration with Enhanced Sensitivity in Macaque Retina. Mol Ther 25 2546 PMID: 28807567


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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).

Reference
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Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!

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