127910-31-0

Basic information

• Product Name: (E)-(+/-)-2-AMINO-4-METHYL-5-PHOSPHONO-3-PENTENOIC ACID
• Synonyms: CGP 37849;(E)-(+/-)-2-AMINO-4-METHYL-5-PHOSPHONO-3-PENTENOIC ACID;dl-2-amino-4-methyl-5-phosphono-3-*pentenoic acid;(3E)-2-Amino-4-methyl-5-phosphono-3-pentanoic acid;(E)-2-Amino-4-methyl-5-phosphonopent-3-enoic acid
• CAS NO: 127910-31-0
• Molecular Formula: C₆H₁₂NO₅P
• Molecular Weight: 209.14
• Product Categories: Glutamate receptor;Glutamate
• Mol File: 127910-31-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 523.1 °C at 760 mmHg
• Flash Point: 270.2 °C
• Appearance: white to beige/
• Density: 1.506 g/cm³
• Storage Temp.: Desiccate at +4°C
• Solubility: H2O: ≥2mg/mL (warmed)
• PKA: 1.83±0.10(Predicted)
• CAS DataBase Reference: (E)-(+/-)-2-AMINO-4-METHYL-5-PHOSPHONO-3-PENTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(+/-)-2-AMINO-4-METHYL-5-PHOSPHONO-3-PENTENOIC ACID(127910-31-0)
• EPA Substance Registry System: (E)-(+/-)-2-AMINO-4-METHYL-5-PHOSPHONO-3-PENTENOIC ACID(127910-31-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 127910-31-0(Hazardous Substances Data)

Usage

Description

(E)-(+/-)-2-AMINO-4-METHYL-5-PHOSPHONO-3-PENTENOIC ACID, also known as CGP 37849, is a chemical compound with potent antagonistic properties at N-methyl-D-aspartate (NMDA) receptors. It is characterized by its ability to modulate the activity of these receptors, which play a crucial role in various neurological processes. The compound exhibits a chiral center, denoted by the (E)-(+/-) notation, indicating the presence of both enantiomers in the mixture.

Uses

Used in Pharmaceutical Industry:
(E)-(+/-)-2-AMINO-4-METHYL-5-PHOSPHONO-3-PENTENOIC ACID is used as an anticonvulsant agent for the treatment of seizure disorders. Its antagonistic action at NMDA receptors helps in reducing the frequency and severity of seizures by modulating the excitatory neurotransmission involved in these conditions.
Additionally, the compound may be used as an anxiolytic agent to counteract the anxiety-inducing effects of NMDA-antagonistic drugs. By blocking the NMDA receptors, CGP 37849 can potentially alleviate the negative side effects associated with the use of certain NMDA antagonists, such as anxiety and agitation.

Biological Activity

Potent, selective and competitive NMDA receptor antagonist (K i = 35 nM). Anticonvulsive following oral administration in vivo .

Upstream product

• 127910-32-1 CGP 39551 
• 115972-26-4 E-2-formylamino-4-methyl-5-diethylphosphono-3-pentenoic acid ethyl ester 

Downstream Products

• 127910-32-1 CGP 39551 

Relevant articles and documents

Unsaturated amino acids

The invention relates to unsaturated amino acids of the formula I STR1 in which R1 represents hydroxy or etherified hydroxy, R2 represents hydrogen, alkyl, hydroxy or etherified hydroxy, R3 represents hydrogen, alkyl, haloalkyl, hydroxyalkyl, lower alkoxyalkyl, arylalkyl, lower alkenyl, halogen or aryl, R4 represents hydrogen, alkyl or aryl, R5 represents hydrogen or alkyl, R6 represents carboxy or esterified or amidated carboxy, R7 represents amino or amino substituted by alkyl or acyl, A represents unsubstituted or alkyl-substituted α,ω-alkylene having from 1 to 3 carbon atoms or represents a bond, and B represents methylene or a bond, with the proviso that A is other than a bond when B represents a bond, and salts thereof. They can be manufactured, for example, in accordance with the Michaelis-Arbuzov reaction and can be used as pharmacologically active substances.