# Icilin

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Icilin
> Markdown URL: https://mediated.wiki/source/Icilin.md
> Source: https://en.wikipedia.org/wiki/Icilin
> Source revision: 1323848625
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Chembox
| Verifiedfields = changed
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| verifiedrevid = 426194395
| ImageFile = Icilin.svg
| ImageSize = 250px
| PIN = 3-(2-Hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1''H'')-one
| OtherNames = 1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-3,6-dihydropyrimidin-2-one<br />AG-3-5
|Section1={{Chembox Identifiers
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| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 36945-98-9
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| UNII = CS70PZQ4QJ
| EINECS = 
| PubChem = 161930
| IUPHAR_ligand = 2429
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 142218
| SMILES = O=C3N(c1c(O)cccc1)C/C=C(/c2cccc([N+]([O-])=O)c2)N3
| 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)
| InChIKey = RCEFMOGVOYEGJN-UHFFFAOYAQ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = RCEFMOGVOYEGJN-UHFFFAOYSA-N
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|Section2={{Chembox Properties
| Formula = C<sub>16</sub>H<sub>13</sub>N<sub>3</sub>O<sub>4</sub>
| MolarMass = 311.29 g/mol
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|Section3={{Chembox Structure
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|Section5={{Chembox Pharmacology
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|Section6={{Chembox Explosive
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|Section7={{Chembox Hazards
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|Section8={{Chembox Related
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}}

'''Icilin''' ('''AG-3-5''') is a [synthetic](/source/chemical_synthesis) super-[agonist](/source/agonist) of the [transient receptor potential M8](/source/TRPM8) (TRPM8) [ion channel](/source/ion_channel). Although structurally not related to [menthol](/source/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.<ref name="pmid6131976">{{cite journal |vauthors=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=10.1111/j.2042-7158.1983.tb04279.x|s2cid=42844929 }}</ref> Despite their similar effects, icilin activates the TRPM8 receptor in a different way than menthol does.<ref name="pmid15190109">{{cite journal |vauthors=Andersson DA, Chase HW, Bevan S |year=2004 |title=TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH |journal=J. Neurosci. |volume=24 |issue=23 |pages=5364–9 |doi=10.1523/JNEUROSCI.0890-04.2004 |pmc=6729305 |pmid=15190109 |doi-access=free |title-link=}}</ref> Icilin has been shown to be effective in the treatment of [pruritus](/source/pruritus) in an experimental model of itch.<ref name="pmid15740597">{{cite journal | last1 = Biró | first1 = T | last2 = Ko | first2 = MC | last3 = Bromm | first3 = B | last4 = Wei | first4 = ET | last5 = Bigliardi | first5 = P | last6 = Siebenhaar | first6 = F | last7 = Hashizume | first7 = H | last8 = Misery | first8 = L | last9 = Bergasa | first9 = NV | last10 = Kamei | first10 = C. | last11 = Schouenborg | first11 = J. | last12 = Roostermann | first12 = D. | last13 = Szabo | first13 = T. | last14 = Maurer | first14 = M. | last15 = Bigliardi-Qi | first15 = M. | last16 = Meingassner | first16 = J. G. | last17 = Hossen | first17 = M. A. | last18 = Schmelz | first18 = M. | last19 = Steinhoff | first19 = M. | title = How best to fight that nasty itch - from new insights into the neuroimmunological, neuroendocrine, and neurophysiological bases of pruritus to novel therapeutic approaches | journal = Experimental Dermatology | volume = 14 | issue = 3 | pages = 225–40 | year = 2005 | pmid = 15740597 | doi = 10.1111/j.0906-6705.2005.0321a.x | s2cid = 23665244 | display-authors = 3 | doi-access = free | hdl = 2437/149579 | hdl-access = free }}</ref> It is now used as a research tool for the study of [TRP channels](/source/Transient_receptor_potential), although despite its high potency it is less selective for TRPM8 over other related ion channels than are other compounds such as [WS-12](/source/WS-12).

== References ==
{{Reflist}}

== External links ==

{{Transient receptor potential channel modulators}}

Category:2-Hydroxyphenyl compounds
Category:3-Nitrophenyl compounds
Category:Ureas
Category:Pyrimidones
Category:Cooling flavors

{{Organic-compound-stub}}

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Adapted from the Wikipedia article [Icilin](https://en.wikipedia.org/wiki/Icilin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Icilin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.