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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
3D model (JSmol )
ChemSpider
ECHA InfoCard
100.164.593
IUPHAR/BPS
UNII
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
O=C3N(c1c(O)cccc1)C/C=C(/c2cccc([N+]([O-])=O)c2)N3
Properties
C16 H13 N3 O4
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 Y N ?)
Infobox references
Chemical compound
Icilin (AG-3-5 ) 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 to menthol.[2] Icilin has been shown to be effective in the treatment of pruritus in an experimental model of itch.[3] It is now used as a research tool for the study of TRP channels , although despite its high potency it is less selective for TRPM8 over other related ion channels than newer compounds such as WS-12 .
References [ ]
^ Wei ET, Seid DA (1983). "AG-3-5: a chemical producing sensations of cold". J. Pharm. Pharmacol . 35 (2): 110–2. doi :10.1111/j.2042-7158.1983.tb04279.x . PMID 6131976 . S2CID 42844929 .
^ 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 . PMC 6729305 . 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 . S2CID 23665244 .
External links [ ]
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ12,14 -prostaglandin J2
α-Sanshool (ginger , Sichuan and melegueta peppers )
Acrolein
Allicin (garlic )
Allyl isothiocyanate (mustard , radish , horseradish , wasabi )
AM404
ASP-7663
Bradykinin
Cannabichromene (cannabis )
Cannabidiol (cannabis )
Cannabigerol (cannabis )
Cinnamaldehyde (cinnamon )
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Cuminaldehyde (cumin )
Curcumin (turmeric )
(celery )
Diallyl disulfide
Dicentrine (Lindera spp.)
Formalin
Gingerols (ginger )
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
(celery , Angelica acutiloba )
Linalool (Sichuan pepper , thyme )
Methylglyoxal
Methyl salicylate (wintergreen )
N-Methylmaleimide
Nicotine (tobacco )
Oleocanthal (olive oil )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
PF-4840154
Phenacyl chloride
Polygodial (Dorrigo pepper )
Shogaols (ginger , Sichuan and melegueta peppers )
Tear gases
Tetrahydrocannabinol (cannabis )
Tetrahydrocannabiorcol
Thiopropanal S-oxide (onion )
Umbellulone (Umbellularia californica )
WIN 55,212-2
Blockers
TRPC
TRPM
TRPML
TRPP
TRPV
Activators
2-APB
5',6'-EET
9-HODE
9-oxoODE
12S-HETE
12S-HpETE
13-HODE
13-oxoODE
20-HETE
α-Sanshool (ginger , Sichuan and melegueta peppers )
Allicin (garlic )
AM404
Anandamide
(Andrographis paniculata )
Camphor (camphor laurel , rosemary , camphorweed , African blue basil , camphor basil )
Cannabidiol (cannabis )
Cannabidivarin (cannabis )
Capsaicin (chili pepper )
Carvacrol (oregano , thyme , pepperwort , wild bergamot , others)
DHEA
Diacyl glycerol
Dihydrocapsaicin (chili pepper )
Estradiol
Eugenol (basil , clove )
Evodiamine (Euodia ruticarpa )
Gingerols (ginger )
GSK1016790A
Heat
Hepoxilin A3
Hepoxilin B3
Homocapsaicin (chili pepper )
Homodihydrocapsaicin (chili pepper )
Incensole (incense )
Lysophosphatidic acid
Low pH (acidic conditions)
Menthol (mint )
N-Arachidonoyl dopamine
N-Oleoylethanolamide
Nonivamide (PAVA) (PAVA spray )
Nordihydrocapsaicin (chili pepper )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
Phenylacetylrinvanil
Phorbol esters (e.g., )
Piperine (black pepper , long pepper )
Polygodial (Dorrigo pepper )
Probenecid
Protons
RhTx
(Ruta graveolens )
Resiniferatoxin (RTX) (Euphorbia resinifera /pooissonii )
Shogaols (ginger , Sichuan and melegueta peppers )
Tetrahydrocannabivarin (cannabis )
Thymol (thyme , oregano )
Tinyatoxin (Euphorbia resinifera /pooissonii )
Tramadol
Vanillin (vanilla )
Zucapsaicin
Blockers
See also: Receptor/signaling modulators • Ion channel modulators
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