ChemicalBook > CAS DataBase List > PEPA

PEPA

Product Name: PEPA
CAS No.: 141286-78-4
Chemical Name: PEPA
Synonyms: PEPA;PEPA;PEPA, 10 mM in DMSO;PEPA,inhibit,Inhibitor,iGluR,Ionotropic glutamate receptors;2-[2,6-Difluoro-4-[[2-[(phenylsulfonyl)amino]ethyl]thio]phenoxy]acetamide;Acetamide, 2-[2,6-difluoro-4-[[2-[(phenylsulfonyl)amino]ethyl]thio]phenoxy]-;2,6-Difluoro-4-[2-(phenylsul-fonyl-amino)-ethyl-thio]-phenoxy-acet-amide (PEPA)
CBNumber: CB0972925
Molecular Formula: C16H16F2N2O4S2
Formula Weight: 402.44
MOL File: 141286-78-4.mol

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PEPA Property

Boiling point:: 617.6±65.0 °C(Predicted)
Density: 1.47±0.1 g/cm3(Predicted)
storage temp.: protect from light
solubility: DMSO: >20mg/mL
form: solid
pka: 10.44±0.40(Predicted)
color: white
InChI: InChI=1S/C16H16F2N2O4S2/c17-13-8-11(9-14(18)16(13)24-10-15(19)21)25-7-6-20-26(22,23)12-4-2-1-3-5-12/h1-5,8-9,20H,6-7,10H2,(H2,19,21)
InChIKey: GTACSIONMHMRPD-UHFFFAOYSA-N
SMILES: C(N)(=O)COC1=C(F)C=C(SCCNS(C2=CC=CC=C2)(=O)=O)C=C1F

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: D8941
Product name: 2,6-Difluoro-4-[2-(phenylsulfonylamino)ethylthio]phenoxyacetamide
Purity: ≥98% (HPLC), solid
Packaging: 5mg
Price: $183
Updated: 2025/07/31

Sigma-Aldrich

Product number: D8941
Product name: 2,6-Difluoro-4-[2-(phenylsulfonylamino)ethylthio]phenoxyacetamide
Purity: ≥98% (HPLC), solid
Packaging: 25mg
Price: $748
Updated: 2025/07/31

Cayman Chemical

Product number: 29190
Product name: PEPA
Packaging: 5mg
Price: $88
Updated: 2024/03/01

Cayman Chemical

Product number: 29190
Product name: PEPA
Packaging: 10mg
Price: $121
Updated: 2024/03/01

TRC

Product number: P999023
Product name: PEPA
Packaging: 25mg
Price: $190
Updated: 2021/12/16

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PEPA Chemical Properties,Usage,Production

Description

PEPA is a positive allosteric modulator (PAM) of AMPA receptors. It selectively increases glutamate-induced currents in X. laevis oocytes expressing the flop isoforms of the AMPA receptor subunits glutamate receptor 3 (GluR3) and GluR4 over the flip isoforms of these subunits at 200 μM. PEPA (10 mg/kg) decreases the latency to find the platform in the Morris water maze, indicating reversal of memory deficits, in a rat model of memory impairment induced by middle cerebral artery occlusion (MCAO). It decreases freezing time in a contextual fear freezing paradigm in mice when administered at a dose of 30 mg/kg.

Uses

PEPA is an allosteric potentiator of AMPA desensitization.

Biological Activity

Novel allosteric potentiator of AMPA receptor desensitization. Slows the rate of onset of desensitization and potentiates steady-state equilibrium currents induced by glutamate with subunit (GluR3/4 > GluR1) and splice variant (flop > flip) selectivity. Ameliorates post-ischemic memory impairment in rats following i.v. administration.

Biochem/physiol Actions

2,6-Difluoro-4-[2-(phenylsul-fonyl-amino)-ethyl-thio]-phenoxy-acet-amide is a structurally novel, selective, high affinity AMPA ionotropic glutamate receptor agonist that reduces ischemia-induced performance deficits in rats.

in vivo

PEPA (30 mg/kg; i.p.; once) decreases freezing time in a contextual fear freezing paradigm in mice^[3].

Animal Model:	Male C57BL/6J mice (10-12 weeks old) were applied stress (a 2 h restraint, a 20 min forced swim, and ether inhalation)^[3]
Dosage:	3 mg/kg, 10 mg/kg, 30 mg/kg
Administration:	i.p.; once
Result:	The significant decrease of the freezing response in the extinction sessions was only seen in the 30 mg/kg.

References

[1] Sekiguchi, M., Fleck, M.W., Mayer, M.L., et al. A novel allosteric potentiator of AMPA receptors: 4-[2-(phenylsulfonylamino)ethylthio]-2,6-difluoro-phenoxyacetamide. J. Neurosci. 17(15), 5760-5771 (1997).
[2] Sekiguchi, M., Yamada, K., Jin, J., et al. The AMPA receptor allosteric potentiator PEPA ameliorates post-ischemic memory impairment. Neuroreport 12(13), 2947-29950 (2001).
[3] KO ZUSHIDA. Facilitation of extinction learning for contextual fear memory by PEPA: a potentiator of AMPA receptors.[J]. Journal of Neuroscience, 2007, 27 1: 158-166. DOI:10.1523/JNEUROSCI.3842-06.2007.

PEPA Preparation Products And Raw materials

Raw materials

Preparation Products

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PEPA Suppliers

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141286-78-4, PEPARelated Search:

Dimethyl sulfoxide PEPA 3-Aminopyridine

PEPA

2-[2,6-Difluoro-4-[[2-[(phenylsulfonyl)amino]ethyl]thio]phenoxy]acetamide

2,6-Difluoro-4-[2-(phenylsul-fonyl-amino)-ethyl-thio]-phenoxy-acet-amide (PEPA)

PEPA,inhibit,Inhibitor,iGluR,Ionotropic glutamate receptors

Acetamide, 2-[2,6-difluoro-4-[[2-[(phenylsulfonyl)amino]ethyl]thio]phenoxy]-

PEPA, 10 mM in DMSO

PEPA

141286-78-4

C16H16N2O4S2F2