(R)-CPP

Name: ( R )-CPP
Brand: Tocris Bioscience
SKU: 0247

Catalog # 0247

Citations (14)

COA / SDS

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Key Product Details

Description:	Potent NMDA antagonist; more active enantiomer of (RS)-CPP
Chemical Name:	3-((R)-2-Carboxypiperazin-4-yl)-propyl-1-phosphonic acid
Molecular Weight:	252.21

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Biological Activity

(R)-CPP is a highly potent NMDA antagonist; more active isomer. Shows some selectivity for GluN2A (formally NR2A) containing receptors (K_i 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

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

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
Solubility	water	25.22	100

Preparing Stock Solutions

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	0.40 mL	1.98 mL	3.96 mL
50 mM	0.08 mL	0.40 mL	0.79 mL

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References

References are publications that support the biological activity of the product.

Feng Structure-activity analysis of a novel NR2C/NR2D-preferring NMDA receptor antagonist: 1-(phenanthrene-2-carbonyl) piperazine-2,3-dicarboxylic acid. Br.J.Pharmacol. 2004 PMID: 14718249
Aebischer 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

Citations for (<em>R</em>)-CPP (14)

Showing 1 - 10 of 14 citations Showing All

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

Zhang et al. (2018) Heparan Sulfate Organizes Neuronal Synapses through Neurexin Partnerships. Cell. 174:1450
PMID: 30100184
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
Chaffiol et al. (2017) A New Promoter Allows Optogenetic Vision Restoration with Enhanced Sensitivity in Macaque Retina. Mol Ther. 25:2546
PMID: 28807567
Pan et al. (2016) Neuronal firing patterns outweigh circuitry oscillations in parkinsonian motor control. J Clin Invest. 126:4516
PMID: 27797341
Tsutsui-Kimura et al. (2015) Milnacipran remediates impulsive deficits in rats with lesions of the ventromedial prefrontal cortex. J Neurosci. 18
PMID: 25522418
Stephany et al. (2014) Plasticity of binocularity and visual acuity are differentially limited by nogo receptor. PLoS One. 34:11631
PMID: 25164659
Higley et al. (2011) Cholinergic interneurons mediate fast VGluT3-dependent glutamatergic transmission in the striatum. PLoS One. 6:e19155
PMID: 21544206
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
Vigot et al. (2006) Differential compartmentalization and distinct functions of GABAB receptor variants. Neuron. 50:589
PMID: 16701209
Mao et al. Characterization and subcellular targeting of GCaMP-type genetically-encoded calcium indicators. Nat Commun. 3:e1796
PMID: 18350138

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