74341-63-2

Basic information

• Product Name: (RS)-AMPA
• Synonyms: D,L-α-AMino-3-hydroxy-5-Methylisoxazole-4-propionic Acid;γ-AMino-3-hydroxy-5-Methylisoxazole-4-propionic Αcid;2-Amino-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propionic acid, 2-Amino-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propanoic acid;3-(3-Hydroxy-5-methylisoxazol-4-yl)-DL-alanine;(R,S)-2-AMINO-3-(3-HYDROXY-5-METHYL-4-ISOXAZOLYL)PROPIONIC ACID;(RS)-AMPA;(R,S)-A-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID;(RS)-ALFA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID
• CAS NO: 74341-63-2
• Molecular Formula: C7H10N2O4
• Molecular Weight: 186.17
• Product Categories: Heterocycles;Heterocyclic Compounds;Neurochemicals;Glutamate receptor;Glutamate
• Mol File: 74341-63-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 240-252 °C
• Boiling Point: 320.64°C (rough estimate)
• Flash Point: 211.2 °C
• Appearance: white/solid
• Density: 1.3962 (rough estimate)
• Refractive Index: 1.4880 (estimate)
• Storage Temp.: 0-6°C
• Solubility: H2O: 1 mg/mL warm
• Water Solubility: Soluble in warm water at 1mg/ml. Also soluble in 0.1M NaOH or 0.1M HCl at approximately 4mg/ml. Soluble in DMSO at 4mg/ml
• Stability: Store in freezer at -20°C
• CAS DataBase Reference: (RS)-AMPA(CAS DataBase Reference)
• NIST Chemistry Reference: (RS)-AMPA(74341-63-2)
• EPA Substance Registry System: (RS)-AMPA(74341-63-2)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 74341-63-2(Hazardous Substances Data)

Usage

Description

(RS)-AMPA, also known as α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid, is a potent and selective agonist of the excitatory neurotransmitter L-glutamic acid. It is a white-to-off white powder and does not interfere with binding sites for kainic acid in vitro. (RS)-AMPA-induced neuronal excitation is not significantly affected by NMDA antagonists. It is also a selective quisqualate agonist.

Uses

Used in Pharmaceutical Industry:
(RS)-AMPA is used as a pharmaceutical agent for its potent and selective agonist properties, targeting the L-glutamic acid receptors in the central nervous system. This makes it a valuable compound for research and development in the treatment of various neurological disorders and conditions related to neurotransmission.
Used in Research and Development:
(RS)-AMPA is used as a research tool for studying the role of L-glutamic acid and its receptors in neuronal excitation and synaptic plasticity. Its selective agonist properties make it an important compound for understanding the underlying mechanisms of neurotransmission and developing new therapeutic strategies for neurological diseases.
Used in Drug Design and Development:
(RS)-AMPA is used as a lead compound in the design and development of new drugs targeting the L-glutamic acid receptors. Its selective agonist properties and understanding of its interactions with other neurotransmitter systems can help in the development of more effective and targeted treatments for neurological disorders.
Used in Neurotransmission Studies:
(RS)-AMPA is used as a key compound in studying the mechanisms of neuronal excitation and the role of L-glutamic acid in synaptic transmission. This helps researchers gain insights into the complex processes involved in neuronal communication and the development of new therapeutic approaches for related conditions.

Biological Activity

Prototypical and defining agonist for the AMPA subgroup of ionotropic glutamate receptors.

InChI:InChI=1/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12)/t5-/m1/s1

Upstream product

• 75989-21-8 4-hydroxymethyl-3-methoxy-5-methylisoxazole 
• 127020-32-0 (RS)-ethyl 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionate 
• 862848-46-2 ethyl (RS)-2-[N-(tert-butoxycarbonyl)amino]-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionate 
• 75989-20-7 ethyl 3-methoxy-5-methylisoxazole-4-carboxylate 
• 75989-22-9 4-(chloromethyl)-3-methoxy-5-methylisoxazole 
• 153201-10-6 4-(bromomethyl)-2-(methoxymethyl)-5-methylisoxazol-3(2H)-one 
• 153124-37-9 3-bromo-4-hydroxymethyl-5-methylisoxazole 
• 153124-43-7 4-bromomethyl-3-methoxy-5-methylisoxazole 
• 153201-11-7 methyl 2-acetamido-2-methoxycarbonyl-3-(2-methoxymethyl-5-methylisoxazolin-3-on-4-yl)propanoate 
• 75989-23-0 diethyl acetamido<(3-methoxy-5-methylisoxazol-4-yl)methyl>malonate 

Relevant articles and documents

Photoactivatable AMPA for the study of glutamatergic neuronal transmission using two-photon excitation

We report a photoactivatable agonist of the AMPA subtype of ionotropic glutamate receptors, TMP-CyHQ-AMPA, which was designed to study the fast excitatory transmission between neurons. Upon visible light excitation, TMP-CyHQ-AMPA quantitatively released AMPA in high quantum yield on an ultra-short timescale. Intriguingly, the photolyisis can be carried out using 2-photon excitation (2PE) with remarkable efficiency, giving a two-photon uncaging action cross section (δu) value of 1.71 GM. TMP-CyHQ-AMPA is soluble in pysiological buffer and no hydrolysis was detected in the absence of light. Molecular docking experiments indicated that the photocaging strategy abolishes the affinity of AMPA for the GluR2 receptor and no GABAergic effects (as commonly observed in caged glutamates) are expected. TMP-CyHQ-AMPA can be used to study glutamatergic neuronal transmission with exceptional spatial-temporal resolution in complex tissue preparations.

Equilibrium control in bromomethylation: An expedient route to 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA)

The excitatory amino acid 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) has been prepared in gram quantities in 42% total yield by a three-step procedure from 3-hydroxy-5-methylisoxazole. It is shown how bromomethylation may be optimized through control of the involved equilibria and how N-protecting methoxymethyl groups can be removed.