Icilin

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IUPACName = 1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-3,6-dihydropyrimidin-2-one
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OtherNames = AG-3-5
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CASNo = 36945-98-9
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PubChem = 161930
SMILES = C1C=C(NC(=O)N1C2=CC=CC=C2O)C3=CC(=CC=C3) [N+] (=O) [O-]
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)/f/h17H
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Formula = C₁₆H₁₃N₃O₄
MolarMass = 311.29 g/mol
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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.cite journal |author=Wei ET, Seid DA |title=AG-3-5: a chemical producing sensations of cold |journal=J. Pharm. Pharmacol. |volume=35 |issue=2 |pages=110–2 |year=1983 |pmid=6131976 |doi=] Despite their similar effects icilin activates the TRPM8 receptor in a different way.cite journal |author=Andersson DA, Chase HW, Bevan S |title=TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH |journal=J. Neurosci. |volume=24 |issue=23 |pages=5364–9 |year=2004 |pmid=15190109 |doi=10.1523/JNEUROSCI.0890-04.2004] It is now used as a research tool for the study of TRP channels.

References

External links

[http://www.caymanchem.com/app/template/Product.vm/catalog/10137/a/z Product sheet of Icilin from Cayman Chemical]