36945-98-9

Basic information

• Product Name: ICILIN
• Synonyms: ICILIN;3,6-DIHYDRO-1-(2-HYDROXYPHENYL)-4-(3-NITROPHENYL)-2(1H)-PYRIMIDINONE;AG-3-5;3,4-DIHYDRO-3-(2-HYDROXYPHENYL)-6-(3-NITROPHENYL)-(1H)-PYRIMIDIN-2-ONE;1-(2-HYDROXYPHENYL)-4-(3-NITROPHENYL)-1,2,3,6-TETRAHYDROPYRIMIDIN-2-ONE;1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one;3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-2(1h)-pyrimidinon;Iciline
• CAS NO: 36945-98-9
• Molecular Formula: C16H13N3O4
• Molecular Weight: 311.29
• Product Categories: Vanilloid/TRPV channel;Inhibitors
• Mol File: 36945-98-9.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 594.8 ºC at 760 mmHg
• Flash Point: 313.5 ºC
• Appearance: yellow/solid
• Density: 1.415 g/cm³
• Vapor Pressure: 9.67E-15mmHg at 25°C
• Refractive Index: 1.672
• Storage Temp.: Store at RT
• Solubility: DMSO: 15 mg/mL, soluble
• PKA: 9.94±0.35(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: ICILIN(CAS DataBase Reference)
• NIST Chemistry Reference: ICILIN(36945-98-9)
• EPA Substance Registry System: ICILIN(36945-98-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: UW7397500
• Hazardous Substances Data: 36945-98-9(Hazardous Substances Data)

Usage

Description

ICILIN, with the chemical formula (36945-98-9), is a synthetic cooling agent that effectively modulates human transient receptor potential cation channel (TRPA1). It demonstrates 2.5 times greater efficacy and 200 times greater potency than menthol in activating cold-sensitive TRP channels. ICILIN inhibits transient receptor potential cation channel subfamily M member 8 (TRPM8) and also modulates calcium release. Additionally, it suppresses transient receptor potential vanilloid subtype 3 (TRPV3). The activator effects of ICILIN require Ca2+ and are pH dependent. ICILIN has been shown to induce G1 arrest in PC-3 prostate cancer cells without causing cell death.

Uses

Used in Pharmaceutical Applications:
ICILIN is used as a cooling agent for modulating human transient receptor potential cation channel (TRPA1), which can be beneficial in various pharmaceutical applications related to pain relief and sensory perception.
Used in Neuronal Applications:
In the field of neuroscience, ICILIN is used as a cooling agent in anterior ventromedial preoptic area (VMPO) neurons, potentially contributing to the understanding of temperature regulation and sensory processing in the brain.
Used in Cancer Research:
ICILIN has demonstrated its potential in cancer research, as it induced G1 arrest in PC-3 prostate cancer cells without causing cell death. This application could lead to the development of novel therapeutic strategies for cancer treatment.

Biological Activity

Cooling agent that activates the novel cold receptors TRPM8 (CMR1) and TRPA1 (ANKTM1/TRPN1), members of the TRP ion channel family. Induces currents in CMR1-expressing HEK-293 cells (EC 50 = 0.36 μ M) more potently than menthol or low temperatures. Produces "wet shakes" in vivo .

Biochem/physiol Actions

Icilin is a potent agonist at the CMR1 cold- and menthol-sensitive receptor.

References

1) McKemy?et al. (2002)?Identification of a cold receptor reveals a general role for TRP channels in thermosensation; Nature,?416?52 2) Andersson?et al. (2004)?TRPM8 activation by menthol, icilin and cold is differentially modulated by intracellular pH; J .Neurosci.,?24?5364 3) Story?et al. (2003)?ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures; Cell,?112?819 4) Chuang?et al. (2004)?The super-cooling agent icilin reveals a mechanism of coincidence detection by a temperature-sensitive TRP channel; Neuron,?43?859 5) Kim?et al. (2011)?Icilin induces G1?arrest through activating JNK and p38 kinase in a TRPM8-independent manner; Biochem. Biophys. Res .Commun.,?406?30

InChI:InChI=1/C16H13N3O4/c20-15-7-2-1-6-14(15)18-9-8-13(17-16(18)21)11-4-3-5-12(10-11)19(22)23/h1-8,10,20H,9H2,(H,17,21)