| Identification | Back Directory | [Name]
(R)-CPP | [CAS]
126453-07-4 | [Synonyms]
D-CPP
(R)-CPP
(R)-CCP
CPP (R)-
rac-(S*)-2-(2,4-Dichlorophenoxy)propanoic acid
rac-(2R*)-2-(2,4-Dichlorophenoxy)propanoic acid
rac-(2R*)-2-(2,4-Dichlorophenoxy)propionic acid
3-((R)-Carboxylpiperazin-4-yl)-propyl-1-phosphonic acid
[3-[(2R)-2-Carboxypiperazin-4-yl]propyl]phosphonic acid
3-((R)-2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID
R(-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID
3-((R)-2-CARBOXYLPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID
2-Piperazinecarboxylic acid, 4-(3-phosphonopropyl)-, (2R)-
3-[(2R)-2-Carboxypiperazine-4-yl]propane-1-ylphosphonic acid | [Molecular Formula]
C8H17N2O5P | [MDL Number]
MFCD00153786 | [MOL File]
126453-07-4.mol | [Molecular Weight]
252.2 |
| Chemical Properties | Back Directory | [Boiling point ]
546.7±60.0 °C(Predicted) | [density ]
1.408±0.06 g/cm3(Predicted) | [storage temp. ]
Desiccate at RT | [solubility ]
Water: 100mM | [form ]
White crystalline powder. | [pka]
1.89±0.20(Predicted) | [color ]
White to off-white | [Water Solubility ]
Soluble to 100 mM in water |
| Hazard Information | Back Directory | [Description]
(R)-CPP is an NMDA receptor antagonist (Ki = 0.14 μM). It binds to NMDA receptors containing GluN2A, GluN2B, GluN2C, and GluN2D subunits with Ki values of 0.04, 0.3, 0.6, and 2 μM, respectively. It inhibits depolarization induced by NMDA in isolated hemisected frog spinal cord (pA2 = 6.56) and NMDA-induced sodium efflux from rat brain slices (pA2 = 6.2). (R)-CPP inhibits the clonic phase of sound-induced seizures in DBA/2 mice (ED50 = 65.8 μmol/kg) and the myoclonic phase of stroboscopic-induced seizures in P. papio photosensitive baboons (ED50 = 127 μmol/kg). | [Uses]
(R)-CPP is a piperazine derivative demonstrating highly potent NMDA receptor antagonism. | [Biological Activity]
Highly potent NMDA antagonist; more active isomer. Shows some selectivity for NR2A-containing receptors (K i values are 0.041, 0.27, 0.63 and 1.99 μ M for inhibition of NR2A-, NR2B-, NR2C- and NR2D-containing recombinant NMDA receptors respectively). | [IC 50]
NMDA Receptor | [storage]
Room temperature (desiccate) | [References]
[1] B. AEBISCHER. ChemInform Abstract: 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-Phosphonoprop-2-enyl)piperazine-2-carboxylic Acid (CPP-ene).[J]. ChemInform, 1989, 20 44. DOI: 10.1002/chin.198944252
[2] P. PAOLETTI J. N. NMDA receptor subunits: Function and pharmacology[J]. Acute Pain, 2007, 9 2: Page 97. DOI: 10.1016/j.acpain.2007.04.009
[3] SMITA PATEL . Anticonvulsant activity of the NMDA antagonists, d(?)4-(3-phosphonopropyl)piperazine-2-carboxylic acid (D-CPP) and d(?)(E)-4-(3-phosphonoprop-2-enyl) piperazine-2-carboxylic acid (D-CPPene) in a rodent and a primate model of reflex epilepsy[J]. Epilepsy Research, 1990, 7 1: Pages 3-10. DOI: 10.1016/0920-1211(90)90049-2 |
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