Icilin

Icilin

Names
Preferred IUPAC name 3-(2-Hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one
Other names 1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-3,6-dihydropyrimidin-2-one AG-3-5
Identifiers
CAS Number	36945-98-9 Y
3D model (Jmol)	Interactive image
ChemSpider	142218 N
ECHA InfoCard	100.164.593
IUPHAR/BPS	2429
PubChem	161930
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) N Key: RCEFMOGVOYEGJN-UHFFFAOYSA-N N 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) Key: RCEFMOGVOYEGJN-UHFFFAOYAQ
SMILES O=C3N(c1c(O)cccc1)C/C=C(/c2cccc([N+]([O-])=O)c2)N3
Properties
Chemical formula	C16H13N3O4
Molar mass	311.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Icilin is a synthetic super-agonist of the transient receptor potential M8 (TRPM8) ion channel. Although structurally not related with menthol it produces an extreme sensation of cold both in humans and animals. It is almost 200 times more potent than menthol and 2.5 times more efficacious. Despite their similar effects icilin activates the TRPM8 receptor in a different way. Icilin is effective in an experimental model of itch. It is now used as a research tool for the study of TRP channels.