L-AP4 Property

Melting point:

207-215 °C

Boiling point:

491.7±55.0 °C(Predicted)

Density 

1.628±0.06 g/cm3(Predicted)

storage temp. 

0-6°C

solubility 

H2O : 50 mg/mL (273.07 mM; Need ultrasonic)

pka

2.19±0.10(Predicted)

form 

solid

color 

White

Water Solubility 

Soluble to 5 mM in water and to 100 mM in 1eq. NaOH

Sensitive 

Light Sensitive

CAS DataBase Reference

23052-81-5(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

ES7191700

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

L-AP4 Chemical Properties,Usage,Production

Description

Metabotropic glutamate receptors (mGluR) function to modulate excitatory synaptic transmission in the brain. Eight subtypes (1-8) and multiple splice variants of the mGluR have been identified and grouped based on their pharmacological properties. Group I mGluRs (subtypes 1 and 5) activate the phosphatidyl inositol pathway, while Group II (2 and 3) and Group III (4, 6, 7, and 8) inhibit adenylyl cyclase. L-AP4, an analog of L-glutamic acid, is a selective Group III mGluR agonist that functions presynaptically to suppress glutamate release (IC₅₀ = 2.5 μM). L-AP4 has been shown to depress synaptic transmission in glutamatergic pathways in the hippocampus, olfactory bulb, and retina as well as act as an agonist at the quisqualate-sensitized AP6 site in hippocampus.

Chemical Properties

white to off-white crystalline powder

Uses

Metabotropic glutamate receptors (mGluR) function to modulate excitatory synaptic transmission in the brain. Eight subtypes (1-8) and multiple splice variants of the mGluR have been identified and grouped based on their pharmacological properties. Group I mGluRs (subtypes 1 and 5) activate the phosphatidyl inositol pathway, while Group II (2 and 3) and Group III (4, 6, 7, and 8) inhibit adenylyl cyclase. L-AP4, an analog of L-glutamic acid, is a selective Group III mGluR agonist that functions presynaptically to suppress glutamate release (IC50 = 2.5 μM). L-AP4 has been shown to depress synaptic transmission in glutamatergic pathways in the hippocampus, olfactory bulb, and retina as well as act as an agonist at the quisqualate-sensitized AP6 site in hippocampus.

Uses

L(+)-2-Amino-4-phosphonobutanoic acid (L-AP4) is a mGluR-4/6 receptor agonist.

Definition

ChEBI: (2S)-2-amino-4-phosphonobutanoic acid is a non-proteinogenc L-alpha-amino acid that is L-alpha-aminobutyric acid in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group. It is a potent and selective agonist for the group III metabotropic glutamate receptors (mGluR4/6/7/8). It has a role as a metabotropic glutamate receptor agonist. It is a non-proteinogenic L-alpha-amino acid and a member of phosphonic acids.

Biological Activity

Selective group III metabotropic glutamate receptor agonist. Synaptic depressant. Agonist at the quisqualate-sensitized AP6 site in hippocampus. Also available as part of the Group III mGlu Receptor Tocriset™ and Mixed mGlu Receptor Tocriset™ .

storage

Room temperature