ICILIN Chemical Properties

Boiling point:

594.8±50.0 °C(Predicted)

Density 

1.415±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO: 15 mg/mL, soluble

form 

solid

pka

9.94±0.35(Predicted)

color 

yellow

Stability:

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

InChI

InChI=1S/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)

InChIKey

RCEFMOGVOYEGJN-UHFFFAOYSA-N

SMILES

C1(=O)N(C2=CC=CC=C2O)CC=C(C2=CC=CC([N+]([O-])=O)=C2)N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UW7397500

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

ICILIN Usage And Synthesis

Description

Icilin (36945-98-9) is an activator of cold-sensitive TRP channels with 2.5-fold greater efficacy and 200-fold greater potency than menthol (EC50?= 0.36 μM for CRM1, rat orthologue of TRPM8).1 Activator at TRPM8 (EC50?= 0.2 μM)2?and ANKTM1(TRPA1)3. Activator effects require Ca2+?and are pH dependent.2,4?Icilin induced G1?arrest in PC-3 prostate cancer cells without cell death.5

Uses

Icilin has been used as cooling agent in anterior ventromedial preoptic area (VMPO) neurons.

Definition

ChEBI: 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one is a C-nitro compound.

General Description

Icilin is a synthetic cooling agent and modulates human transient receptor potential cation channel (TRPA1). Icilin inhibits transient receptor potential cation channel subfamily M member 8 (TRPM8) and modulates calcium release. Icilin also suppresses transient receptor potential vanilloid subtype 3 (TRPV3).

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.

storage

Room temperature

References

[1] DAVID D. MCKEMY  David J  Werner M Neuhausser. Identification of a cold receptor reveals a general role for TRP channels in thermosensation[J]. Nature, 2002, 416 6876: 52-58. DOI:10.1038/nature719
[2] DAVID A ANDERSSON  Stuart B  Henry W N Chase. TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH.[J]. Journal of Neuroscience, 2004, 24 23: 5364-5369. DOI:10.1523/jneurosci.0890-04.2004
[3] GINA M STORY. ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures.[J]. Cell, 2003, 112 6: 819-829. DOI:10.1016/s0092-8674(03)00158-2
[4] HUAI-HU CHUANG  David J  Werner M Neuhausser. The super-cooling agent icilin reveals a mechanism of coincidence detection by a temperature-sensitive TRP channel.[J]. Neuron, 2004, 43 6: 859-869. DOI:10.1016/j.neuron.2004.08.038
[5] SU-HWA KIM . Icilin induces G1 arrest through activating JNK and p38 kinase in a TRPM8-independent manner[J]. Biochemical and biophysical research communications, 2011, 406 1: Pages 30-35. DOI:10.1016/j.bbrc.2011.01.094

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