126453-07-4

Basic information

• Product Name: (R)-CPP
• Synonyms: (R)-CPP;(R)-CCP;R(-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID;D-CPP;3-((R)-2-CARBOXYLPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID;3-((R)-2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID;3-((R)-Carboxylpiperazin-4-yl)-propyl-1-phosphonic acid;CPP (R)-
• CAS NO: 126453-07-4
• Molecular Formula: C8H17N2O5P
• Molecular Weight: 252.2
• Product Categories: Glutamate receptor;Glutamate
• Mol File: 126453-07-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 546.7°C at 760 mmHg
• Flash Point: 284.4°C
• Appearance: /
• Density: 1.408g/cm³
• Vapor Pressure: 2.14E-13mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: Desiccate at RT
• PKA: 1.89±0.20(Predicted)
• CAS DataBase Reference: (R)-CPP(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-CPP(126453-07-4)
• EPA Substance Registry System: (R)-CPP(126453-07-4)

Safety Data

• Hazardous Substances Data: 126453-07-4(Hazardous Substances Data)

Usage

Description

(R)-CPP, also known as (+)-3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid, is a potent and selective NMDA receptor antagonist. It is a piperazine derivative that demonstrates highly potent NMDA receptor antagonism, with a Ki value of 0.14 μM. (R)-CPP binds to NMDA receptors containing various GluN2 subunits, including GluN2A, GluN2B, GluN2C, and GluN2D, with Ki values ranging from 0.04 to 2 μM. (R)-CPP has been shown to inhibit depolarization induced by NMDA in isolated hemisected frog spinal cord and NMDA-induced sodium efflux from rat brain slices. Additionally, (R)-CPP has been found to inhibit the clonic phase of sound-induced seizures in DBA/2 mice and the myoclonic phase of stroboscopic-induced seizures in P. papio photosensitive baboons.

Uses

Used in Pharmaceutical Industry:
(R)-CPP is used as a research compound for studying the role of NMDA receptors in various neurological disorders and conditions. Its potent antagonism of NMDA receptors makes it a valuable tool in understanding the mechanisms of excitatory neurotransmission and the potential therapeutic effects of NMDA receptor modulation.
Used in Neurological Research:
(R)-CPP is used as a pharmacological agent for investigating the involvement of NMDA receptors in seizure activity and other neurological conditions. Its ability to inhibit the clonic phase of sound-induced seizures in DBA/2 mice and the myoclonic phase of stroboscopic-induced seizures in P. papio photosensitive baboons highlights its potential use in the development of treatments for epilepsy and other seizure-related disorders.
Used in Drug Development:
(R)-CPP serves as a lead compound in the development of new drugs targeting NMDA receptors for the treatment of neurological disorders. Its high potency and selectivity for NMDA receptors containing specific GluN2 subunits make it a promising candidate for the design of more effective and targeted therapies.

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).

InChI:InChI=1/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

Upstream product

• 117414-78-5 (R,E)-4-<3-(diethoxyphosphinyl)prop-2-enyl>piperazine-2-carboxylic acid 
• 117414-74-1 (R,E)-4-(3-phosphonoprop-2-enyl)piperazine-2-carboxylic acid 

Relevant articles and documents

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)

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