4'-CHLORO-3-METHOXYCINNAMANILIDE Chemical Properties

Melting point:

165-167℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO: 13 mg/mL, soluble

form 

solid

color 

off-white

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924.29.7790

MSDS

• Language:English Provider:SigmaAldrich

4'-CHLORO-3-METHOXYCINNAMANILIDE Usage And Synthesis

Description

SB-366791 (472981-92-3) is a potent (IC50 = 0.7 μM) and selective TRPV1 blocker.1,2 Selective for TRPV1 in a panel of 47 different binding assays.

Uses

N-(4-Methoxyphenyl)-4-chlorocinnamamide is a novel, potent, and selective cinnamide TRPV1 antagonist. Also a useful tool to further study the biology of TRPV1.

Uses

SB-366791 has been used as a transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonist:

• to infer the in vitro and in vivo pharmacology of (E)-3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamide (AMG 9810)
• to study its effects on sodium hydrogen sulfide (NaHS) or capsaicin-induced contractile activity
• to study the inhibitory potency of phoneutria toxin (PnTx3-5) (native and recombinant) on various responses mediated by transient receptor potential cation channel subfamily V member 1 (TRPV1)

Definition

ChEBI: 3-(4-chlorophenyl)-N-(3-methoxyphenyl)-2-propenamide is a member of cinnamamides and a secondary carboxamide.

Biological Activity

Potent, selective and competitive vanilloid TRPV1 (VR1) receptor antagonist (pA 2 = 7.71 at hVR1); antagonizes hTRPV1 receptors activated by agonists, noxious heat, but not protons. Displays selectivity over a wide range of receptors and systems including CB 1 and CB 2 receptors, voltage-gated Ca 2+ channels and the hyperpolarization-activated current (I h ). Also available as part of the Vanilloid TRPV1 Receptor Tocriset™ .

Biochem/physiol Actions

SB-366791 might exhibit analgesic properties on bone cancer-related pain behavior.

storage

Store at RT

References

1) Gunthorpe, et al., (2004) Identification and characterization of SB-366791, a potent and selective vanilloid receptor (VR1/TRPV1) antagonist; Neuropharmacology 46 133 2) Varga et al. (2005) Effects of the novel TRPV1 receptor antagonist SB366791 in vitro and in vivo in the rat; Neurosci. Lett.. 385 137

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