Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H13N3O4 |
| Molecular Weight | 311.2921 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=CC=C1N2CC=C(NC2=O)C3=CC=CC(=C3)[N+]([O-])=O
InChI
InChIKey=RCEFMOGVOYEGJN-UHFFFAOYSA-N
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)
| Molecular Formula | C16H13N3O4 |
| Molecular Weight | 311.2921 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16920620 | https://www.ncbi.nlm.nih.gov/pubmed/11882888 | https://www.ncbi.nlm.nih.gov/pubmed/17353192
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16920620 | https://www.ncbi.nlm.nih.gov/pubmed/11882888 | https://www.ncbi.nlm.nih.gov/pubmed/17353192
AG-3-5 (also known as icilin) was first identified as a super-cooling agent in the early 1980s and bears little resemblance to menthol structurally. Icilin is able to activate both TRPM8 and TRPA1 channel activity. Icilin alleviates pain sensation in animal models.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16920620 | https://www.ncbi.nlm.nih.gov/pubmed/11882888
Curator's Comment: Icilin is CNS active in animals. No human data available.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| TRPM8 activation attenuates inflammatory responses in mouse models of colitis. | 2013-04-30 |
|
| Lack of transient receptor potential melastatin 8 activation by phthalate esters that enhance contact hypersensitivity in mice. | 2013-03-13 |
|
| Transient receptor potential vanilloid-1 (TRPV1) is a mediator of lung toxicity for coal fly ash particulate material. | 2012-03 |
|
| Design and optimization of benzimidazole-containing transient receptor potential melastatin 8 (TRPM8) antagonists. | 2011-01-13 |
|
| Chronic treatment with NGF induces spontaneous fluctuations of intracellular Ca(2+) in icilin-sensitive dorsal root ganglion neurons of the rat. | 2010-12 |
|
| Sensitization of capsaicin and icilin responses in oxaliplatin treated adult rat DRG neurons. | 2010-11-24 |
|
| Expression of transient receptor potential channel vanilloid (TRPV) 1–4, melastin (TRPM) 5 and 8, and ankyrin (TRPA1) in the normal and methimazole-treated mouse olfactory epithelium. | 2010-11 |
|
| Dissociation of μ- and δ-opioid inhibition of glutamatergic synaptic transmission in superficial dorsal horn. | 2010-10-26 |
|
| Inhibition of the cardiac L-type calcium channel current by the TRPM8 agonist, (-)-menthol. | 2010-10 |
|
| Gating of transient receptor potential melastatin 8 (TRPM8) channels activated by cold and chemical agonists in planar lipid bilayers. | 2010-09-15 |
|
| Contribution of the S5-pore-S6 domain to the gating characteristics of the cation channels TRPM2 and TRPM8. | 2010-08-27 |
|
| TRPM8, but not TRPA1, is required for neural and behavioral responses to acute noxious cold temperatures and cold-mimetics in vivo. | 2010-08 |
|
| Intact cutaneous C fibre afferent properties in mechanical and cold neuropathic allodynia. | 2010-07 |
|
| Grueneberg ganglion neurons are finely tuned cold sensors. | 2010-06-02 |
|
| Estrogen regulation of TRPM8 expression in breast cancer cells. | 2010-05-19 |
|
| (-)-Menthylamine derivatives as potent and selective antagonists of transient receptor potential melastatin type-8 (TRPM8) channels. | 2010-05-01 |
|
| The roles of iPLA2, TRPM8 and TRPA1 in chemically induced cold hypersensitivity. | 2010-01-21 |
|
| Modulation of the cold-activated cation channel TRPM8 by surface charge screening. | 2010-01-15 |
|
| Amiloride-sensitive channels are a major contributor to mechanotransduction in mammalian muscle spindles. | 2010-01-01 |
|
| Characterization of selective TRPM8 ligands and their structure activity response (S.A.R) relationship. | 2010 |
|
| Effects of transient receptor potential (TRP) channel agonists and antagonists on slowly adapting type II mechanoreceptors in the rat sinus hair follicle. | 2009-12 |
|
| Differential role of the menthol-binding residue Y745 in the antagonism of thermally gated TRPM8 channels. | 2009-11-03 |
|
| Non-neuronal expression of transient receptor potential type A1 (TRPA1) in human skin. | 2009-09 |
|
| Tumor necrosis factor-alpha (TNF-alpha) enhances functional thermal and chemical responses of TRP cation channels in human synoviocytes. | 2009-08-20 |
|
| Letter to the editor: "Is menthol- or icilin-induced vasodilation mediated by the activation of TRPM8?". | 2009-08 |
|
| Involvement of increased expression of transient receptor potential melastatin 8 in oxaliplatin-induced cold allodynia in mice. | 2009-07-17 |
|
| Dose-dependent effects of icilin on thermal preference in the hindpaw and face of rats. | 2009-06 |
|
| Primary afferents with TRPM8 and TRPA1 profiles target distinct subpopulations of rat superficial dorsal horn neurones. | 2009-06 |
|
| Transient receptor potential melastatin 8 channel involvement in the regulation of vascular tone. | 2009-06 |
|
| Evolution of thermal response properties in a cold-activated TRP channel. | 2009-05-29 |
|
| Icilin-induced wet-dog shakes in rats are dependent on NMDA receptor activation and nitric oxide production. | 2009-05 |
|
| Comparative modeling of the quaternary structure for the human TRPM8 channel and analysis of its binding features. | 2009-05 |
|
| Lipid raft segregation modulates TRPM8 channel activity. | 2009-04-03 |
|
| Adult rat odontoblasts lack noxious thermal sensitivity. | 2009-04 |
|
| Inhibition of TRPM8 by icilin distinct from desensitization induced by menthol and menthol derivatives. | 2009-02-13 |
|
| Pore dilation occurs in TRPA1 but not in TRPM8 channels. | 2009-01-21 |
|
| [Modulation of the smooth muscle contractions of the rat vas deferens by TRPM8 channel agonist menthol]. | 2009 |
|
| Inorganic polyphosphate modulates TRPM8 channels. | 2009 |
|
| Impairment by allyl isothiocyanate of gastric epithelial wound repair through inhibition of ion transporters. | 2008-12 |
|
| HC-030031, a TRPA1 selective antagonist, attenuates inflammatory- and neuropathy-induced mechanical hypersensitivity. | 2008-10-27 |
|
| Menthol derivative WS-12 selectively activates transient receptor potential melastatin-8 (TRPM8) ion channels. | 2008-10 |
|
| Inhibition by the cold receptor agonists menthol and icilin of airway smooth muscle contraction. | 2008-10 |
|
| TRPA1 channels mediate cold temperature sensing in mammalian vagal sensory neurons: pharmacological and genetic evidence. | 2008-07-30 |
|
| Comparison of icilin- and cold-evoked responses of spinal neurones, and their modulation of mechanical activity, in a model of neuropathic pain. | 2008-06-18 |
|
| Plant-derived cannabinoids modulate the activity of transient receptor potential channels of ankyrin type-1 and melastatin type-8. | 2008-06 |
|
| Citral sensing by Transient [corrected] receptor potential channels in dorsal root ganglion neurons. | 2008-05-07 |
|
| Molecular and cellular limits to somatosensory specificity. | 2008-04-18 |
|
| ThermoTRP channels in nociceptors: taking a lead from capsaicin receptor TRPV1. | 2008-03 |
|
| Partial restoration of mutant enzyme homeostasis in three distinct lysosomal storage disease cell lines by altering calcium homeostasis. | 2008-02 |
|
| Species-specific pharmacology of Trichloro(sulfanyl)ethyl benzamides as transient receptor potential ankyrin 1 (TRPA1) antagonists. | 2007-12-17 |
Sample Use Guides
topical application of 80-200 uM icilin alleviates pain sensations in rats
Route of Administration:
Topical
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:08:55 GMT 2025
by
admin
on
Mon Mar 31 21:08:55 GMT 2025
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| Record UNII |
CS70PZQ4QJ
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| Record Status |
Validated (UNII)
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| Record Version |
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C490483
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m6195
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DTXSID70190442
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CS70PZQ4QJ
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ICILIN
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161930
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36945-98-9
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