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 ;
3D model (JSmol)	Interactive image;
ChemSpider	142218 ;
ECHA InfoCard	100.164.593
IUPHAR/BPS	2429;
PubChem CID	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) Key: RCEFMOGVOYEGJN-UHFFFAOYSA-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).
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	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.^[1] Despite their similar effects icilin activates the TRPM8 receptor in a different way.^[2] Icilin is effective in an experimental model of itch.^[3] It is now used as a research tool for the study of TRP channels.

References

↑ Wei ET, Seid DA (1983). "AG-3-5: a chemical producing sensations of cold". J. Pharm. Pharmacol. 35 (2): 110–2. PMID 6131976.
↑ Andersson DA, Chase HW, Bevan S (2004). "TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH". J. Neurosci. 24 (23): 5364–9. doi:10.1523/JNEUROSCI.0890-04.2004. PMID 15190109.
↑ Biró, T; Ko, MC; Bromm, B; Wei, ET; Bigliardi, P; Siebenhaar, F; Hashizume, H; Misery, L; et al. (2005). "How best to fight that nasty itch - from new insights into the neuroimmunological, neuroendocrine, and neurophysiological bases of pruritus to novel therapeutic approaches". Experimental Dermatology. 14 (3): 225–40. doi:10.1111/j.0906-6705.2005.0321a.x. PMID 15740597.

External links

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[pmid6131976-1] Wei ET, Seid DA (1983). "AG-3-5: a chemical producing sensations of cold". J. Pharm. Pharmacol. 35 (2): 110–2. PMID 6131976.

[pmid15190109-2] Andersson DA, Chase HW, Bevan S (2004). "TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH". J. Neurosci. 24 (23): 5364–9. doi:10.1523/JNEUROSCI.0890-04.2004. PMID 15190109.

[pmid15740597-3] Biró, T; Ko, MC; Bromm, B; Wei, ET; Bigliardi, P; Siebenhaar, F; Hashizume, H; Misery, L; et al. (2005). "How best to fight that nasty itch - from new insights into the neuroimmunological, neuroendocrine, and neurophysiological bases of pruritus to novel therapeutic approaches". Experimental Dermatology. 14 (3): 225–40. doi:10.1111/j.0906-6705.2005.0321a.x. PMID 15740597.