20263-07-4

Basic information

• Product Name: DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID
• Synonyms: (+/-)-AP-4;AP-4;DL-2-AMINO-4-PHOSPHONOBUTANOIC ACID;DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID;DL-AP4;(+/-)-2-AMINO-4-PHOSPHONOBUTYRIC ACID;DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID (DL-AP4);DL-APB
• CAS NO: 20263-07-4
• Molecular Formula: C4H10NO5P
• Molecular Weight: 183.1
• Product Categories: Glutamate receptor;Glutamate
• Mol File: 20263-07-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 225 °C
• Boiling Point: 491.7 °C at 760 mmHg
• Flash Point: 251.2 °C
• Appearance: white/solid
• Density: 1.628 g/cm³
• Vapor Pressure: 5.18E-11mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: 0-6°C
• BRN: 2093908
• CAS DataBase Reference: DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID(20263-07-4)
• EPA Substance Registry System: DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID(20263-07-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 20263-07-4(Hazardous Substances Data)

Usage

Description

DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID, also known as DL-AP4, is a compound that acts as a group III nonselective metabotropic glutamate receptor (mGluR) agonist. It is particularly effective as an agonist for L-2-amino-4-phosphonobutyric acid (L-AP4), which shows close to 500-fold selectivity for group III mGluRs. This property makes it a valuable compound for various applications in scientific research and medical studies.

Uses

Used in Ophthalmology:
DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID is used as a glutamic acid receptor blocker for eye tissue electroretinography studies. Its application in this field is crucial for understanding the function and response of the retina to light stimulation, which can be essential for diagnosing and treating various eye conditions.
Used in Neuropharmacology Research:
As a group III mGluR agonist, DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID is used in neuropharmacological research to study the role of metabotropic glutamate receptors in the central nervous system. This can help in understanding the underlying mechanisms of various neurological disorders and potentially contribute to the development of new therapeutic strategies.
Used in Drug Development:
The selective agonist properties of DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID make it a valuable compound for drug development, particularly in the area of central nervous system disorders. Its ability to modulate group III mGluRs can be exploited to design new drugs targeting these receptors, which may have therapeutic benefits for conditions such as epilepsy, Parkinson's disease, and other neurological disorders.

Biological Activity

Broad spectrum EAA ligand. See separate isomers (D-(-)-2-Amino-4-phosphonobutyric acid and L-(+)-2-Amino-4-phosphonobutyric acid).

InChI:InChI=1/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)

Upstream product

• 86554-31-6 2-Amino-4-(dimethoxy-phosphoryl)-butyric acid methyl ester 

Relevant articles and documents

PREPARATION D'ACIDES AMINOCARBOXY-ALKYLPHOSPHONIQUES OPTIQUEMENT ACTIFS

In aqueous solution ω-formylalkylphosphonates in the presence of hydrogen cyanide and (S) (-) α-methylbenzylamine give optically active aminonitriles with an enantiomeric excess of 50percent.Phosphonic aminonitriles are submitted to acid hydrolysis, then esterified and debenzylated without any epimerization.The separation is performed either with the acid or with the ester.All the operations are monitored by NMR (1H, 13C, 31P) and whenever possible, by GC.