472981-92-3

Basic information

• Product Name: 4'-CHLORO-3-METHOXYCINNAMANILIDE
• Synonyms: N-(3-METHOXYPHENYL)-4-CHLOROCINNAMIDE;SB 366791;4'-CHLORO-3-METHOXYCINNAMANILIDE;3-(4-Chlorophenyl)-N-(3-methoxyphenyl)-2-propenamide;2-Propenamide,3-(4-chlorophenyl)-N-(3-methoxyphenyl)-
• CAS NO: 472981-92-3
• Molecular Formula: C16H14ClNO2
• Molecular Weight: 287.74
• Product Categories: Vanilloid/TRPV channel
• Mol File: 472981-92-3.mol

Chemical Properties

• Melting Point: 165-167℃
• Boiling Point: 494.2°Cat760mmHg
• Flash Point: 252.7°C
• Appearance: off-white/solid
• Density: 1.265g/cm³
• Vapor Pressure: 6.56E-10mmHg at 25°C
• Refractive Index: 1.65
• Storage Temp.: Store at RT
• Solubility: DMSO: 13 mg/mL, soluble
• 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.
• CAS DataBase Reference: 4'-CHLORO-3-METHOXYCINNAMANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-CHLORO-3-METHOXYCINNAMANILIDE(472981-92-3)
• EPA Substance Registry System: 4'-CHLORO-3-METHOXYCINNAMANILIDE(472981-92-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 472981-92-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
4'-CHLORO-3-METHOXYCINNAMANILIDE is used as a research compound for investigating the role of TRPV1 in various physiological and pathological processes. Its potent and selective antagonism of TRPV1 makes it a valuable tool for understanding the channel's involvement in pain sensation, inflammation, and other related conditions.
Used in Drug Development:
In the pharmaceutical industry, 4'-CHLORO-3-METHOXYCINNAMANILIDE is used as a lead compound for the development of new drugs targeting TRPV1. Its antagonistic properties could potentially be harnessed to create medications for treating pain, inflammation, and other TRPV1-related disorders.
Used in In Vitro and In Vivo Pharmacology Studies:
4'-CHLORO-3-METHOXYCINNAMANILIDE is used as a TRPV1 antagonist in both in vitro and in vivo pharmacology studies. It helps researchers infer the effects of other compounds on sodium hydrogen sulfide (NaHS) or capsaicin-induced contractile activity and study the inhibitory potency of various agents on responses mediated by TRPV1.
Used in Ion Channel Research:
In the field of ion channel research, 4'-CHLORO-3-METHOXYCINNAMANILIDE is used as a specific blocker of TRPV1 channels. This allows scientists to explore the channel's function and its potential as a therapeutic target for various diseases and conditions.

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.

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

InChI:InChI=1/C16H14ClNO2/c1-20-15-4-2-3-14(11-15)18-16(19)10-7-12-5-8-13(17)9-6-12/h2-11H,1H3,(H,18,19)/b10-7+