100828-16-8

Basic information

• Product Name: (+/-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID
• Synonyms: (RS)-CPP;(RS)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID;(+/-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID;DL-CPP;(+/-)-CPP;(+/-)-CPP POTENT AND SELECTIVE;2-Piperazinecarboxylic acid, 4-(3-phosphonopropyl)-;2-Piperazinecarboxylic acid, 4-(3-phosphonopropyl)-, (+-)-
• CAS NO: 100828-16-8
• Molecular Formula: C8H17N2O5P
• Molecular Weight: 252.2
• Product Categories: Glutamate receptor;pharmaceutical intermediates
• Mol File: 100828-16-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 546.7°Cat760mmHg
• Flash Point: 284.4°C
• Appearance: white/solid
• Density: 1.408g/cm³
• Vapor Pressure: 2.14E-13mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: Desiccate at RT
• Solubility: H2O: 99.2 mg/mL
• PKA: 1.89±0.20(Predicted)
• CAS DataBase Reference: (+/-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID(100828-16-8)
• EPA Substance Registry System: (+/-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID(100828-16-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-26-36
• WGK Germany: 3
• Hazardous Substances Data: 100828-16-8(Hazardous Substances Data)

Usage

Description

(+/-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID, also known as (+)-3-(2-Carboxypiperazin-4-yl)-propyl-1-phosphoric Acid, is a chemical compound that exhibits NMDA antagonistic activity. This property allows it to interact with the NMDA receptors in the central nervous system, potentially offering therapeutic benefits in various medical conditions.

Uses

Used in Pharmaceutical Industry:
(+/-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID is used as a pharmaceutical agent for its NMDA antagonistic activity. It is employed in the development of medications aimed at treating neurological disorders and conditions that involve the overstimulation of NMDA receptors, such as Alzheimer's disease, Parkinson's disease, and neuropathic pain.
Used in Research Applications:
In the field of scientific research, (+/-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID serves as a valuable tool for studying the role of NMDA receptors in various physiological and pathological processes. It helps researchers understand the mechanisms underlying receptor function and develop new therapeutic strategies for related diseases.
Used in Drug Development:
(+/-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID is utilized in the development of new drugs targeting the NMDA receptor pathway. Its antagonistic properties make it a promising candidate for the creation of medications that can modulate NMDA receptor activity, potentially leading to improved treatments for a range of neurological and psychiatric conditions.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 5193, 1989 DOI: 10.1016/S0040-4039(01)93739-6

Biological Activity

Potent NMDA antagonist. See separate isomer (3-((R)-2-Carboxypiperazin-4-yl)-propyl-1-phosphonicacid ).

Biochem/physiol Actions

Potent and selective NMDA glutamate receptor antagonist; anticonvulsant.

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)

Upstream product

• 146398-98-3 (+/-)-Ethyl 4-<3-(diethoxyphosphinyl)propyl>piperazine-2-carboxylate 
• 146398-95-0 (+/-)-tert-Butyl 4-<3-(diethoxyphosphinyl)propyl>piperazine-2-carboxylate 
• 156833-99-7 (+/-)-2-carboxamido-4-<3-(diethoxyphosphinyl)propyl>piperazine 
• 98-96-4 pyrazinamide 
• 84501-64-4 2-aminocarbonylpiperazine 
• 89941-07-1 ethyl 2-piperazinecarboxylate 
• 146398-94-9 (+/-)-tert-Butyl piperazine-2-carboxylate 
• 146398-93-8 (+/-)-tert-Butyl 1,4-dibenzylpiperazine-2-carboxylate 
• 2762-32-5 piperazine-2-carboxylic acid 
• 1475-93-0 diethyl 3-bromo-prop-2-enyl-1-phosphonate 

Relevant articles and documents

Substituted piperazine-2-carboxylic acids and derivatives thereof

Compounds of the general formula STR1 wherein X is a C 1 -C 6, straight chain saturated or unsaturated hydrocarbyl group, the group R 4 and the group Y are situated in any position in this chain and wherein at least one of the hydrogen atoms in X can be a heavy isotope of hydrogen;R 4 is hydrogen or an alkyl, alkoxy, hydroxy, aryl, aryloxy, aralkyl, aralkoxy, aralkylamino, or morpholino group wherein the alkyl or aryl part of any one of said groups may be substituted by one or more halogeno groups; or R 4, together with at least one carbon atom of the group X, forms a carbocyclic or heterocyclic ring of 5 to 6 ring atoms;Y is an acidic or related group giving rise to one or more electronegative sites in the group; or R 4 --X--Y represents a carboxylic acyl group;R is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl;R 1 is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group;R 2 R 3 and R 5 which may be the same or different is each hydrogen or an alkyl, hydroxy, alkoxy, carboxy, alkyloxycarbonyl, halo, aryl, haloaryl or aryloxycarbonyl group; orR 2 and R 3 together with the carbon atoms to which they are attached form a ring system orR 3 and R 4 together and/or R 3 and X together form one or more than one ring systems, or a physiologically acceptable salt thereof have activity in the central nervous system.

A convenient synthesis of (±)-2-carboxy-4-(3-phosphonopropyl)piperazine (CPP)

A short and convenient route to the N-methyl-D-aspartate (NMDA) antagonist 2-carboxy-4-(3-phosphonopropyl)piperazine (CPP), involving selective N-4 alkylation of piperazine-2-carboxylic acid esters, is described. The method uses readily available starting