An NMDA receptor antagonist
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(R)-CPP

Item No. 21569

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R)-4-(3-phosphonopropyl)-2-piperazinecarboxylic acid
CAS Number
126453-07-4
Molecular Formula
C8H17N2O5P
Formula Weight
252.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: 100mM
SMILES
OP(CCCN1CCN[C@@H](C(O)=O)C1)(O)=O
InChi Code
InChI=1S/C8H17N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h7,9H,1-6H2,(H,11,12)(H2,13,14,15)/t7-/m1/s1
InChi Key
CUVGUPIVTLGRGI-SSDOTTSWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $186

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    10 mg

    $351

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    25 mg

    $775

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    Product Description

    (R)-CPP is an NMDA receptor antagonist (Ki = 0.14 µM).1 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.2 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).1 (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).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Aebischer, B., Frey, P., Haeter, H.-P., et al. 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). Helv. Chim. Acta 72(5), 1043-1051 (1989).

    2. Peoletti, P., and Neyton, J. NMDA receptor subunits: Function and pharmacology. Curr. Opin. Pharmacol. 7(1), 39-47 (2007).

    3. Patel, S., Chapman, A.G., Graham, J.L., et al. 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. Epilepsy Res. 7(1), 3-10 (1990).