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SML0206

Sigma-Aldrich

EAA-090

≥98% (HPLC)

Synonym(s):

P-[2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethyl]-phosphonic acid, WAY-126090

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About This Item

Empirical Formula (Hill Notation):
C9H13N2O5P
CAS Number:
144912-63-0
Molecular Weight:
260.18
MDL number:
MFCD00912427
UNSPSC Code:
12352200
PubChem Substance ID:
329825228

Assay

≥98% (HPLC)

form

powder

color

light yellow to yellow

solubility

H2O: ≥2 mg/mL

originator

Wyeth

storage temp.

2-8°C

SMILES string

OP(O)(=O)CCN1CCCNC2=C1C(=O)C2=O

InChI

1S/C9H13N2O5P/c12-8-6-7(9(8)13)11(3-1-2-10-6)4-5-17(14,15)16/h10H,1-5H2,(H2,14,15,16)

InChI key

BDABGOLMYNHHTR-UHFFFAOYSA-N

Application

EAA-090 was used to study the role of glutamate receptor-mediated signaling in the formation of filipodia and secondary dendrites in rat hippocampal neurons.

Biochem/physiol Actions

EAA-090 inhibits the binding of ligands to glutamate receptors and blocks NMDA-induced currents. It is neuroprotective against glutamate and ischemia-induced toxicity.
EAA-090 is a potent NMDA receptor antagonist with neuroprotective properties. In isoflurane-anesthetized dogs, EAA-090 reduces the minimum alveolar concentration (MAC) of isoflurane and increases systolic, mean, and diastolic arterial blood pressure.

Features and Benefits

This compound was developed by Wyeth. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P264 - P301 + P310

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
111M4603V

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Lucy Sun et al.
The Journal of pharmacology and experimental therapeutics, 310(2), 563-570 (2004-04-13)
Two novel N-methyl-d-aspartate (NMDA) antagonists with unique chemical structures, EAA-090 (2-[8,9-dioxo-2, 6-diazabicyclo[5.2.0]non-1(7)-en2-yl]ethylphosphonic acid) and EAB-318 (R-alpha-amino-5-chloro-1-(phosphonomethyl)-1H-benzimidazole-2-propanoic acid hydrochloride), were compared with CGS-19755 (Selfotel) in ligand binding, electrophysiology, and neuroprotection assays. CGS-19755, EAA-090 and EAB-318 inhibited [(3)H]3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid binding to NMDA
Frank Henle et al.
Naunyn-Schmiedeberg's archives of pharmacology, 385(2), 171-180 (2011-10-29)
GluN receptors are heteromers of obligatory GluN1 subunits and GluN2(A-D) subunits. In the present study, we addressed the question whether GluN2A and GluN2B subunits play distinct roles in the formation of filopodia and dendrites during the early development of hippocampal

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