I9532
Icilin
≥97% (HPLC), CMR1 receptor agonist, solid
Synonym(s):
1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidin-2-one, AG-3-5
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About This Item
Empirical Formula (Hill Notation):
C16H13N3O4
CAS Number:
Molecular Weight:
311.29
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
Icilin, ≥97% (HPLC), solid
SMILES string
Oc1ccccc1N2CC=C(NC2=O)c3cccc(c3)[N+]([O-])=O
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)
InChI key
RCEFMOGVOYEGJN-UHFFFAOYSA-N
assay
≥97% (HPLC)
form
solid
color
yellow
solubility
DMSO: 15 mg/mL
Quality Level
Related Categories
Application
Icilin has been used as cooling agent in anterior ventromedial preoptic area (VMPO) neurons.
Biochem/physiol Actions
Icilin is a potent agonist at the CMR1 cold- and menthol-sensitive receptor.
General description
Icilin is a synthetic cooling agent and modulates human transient receptor potential cation channel (TRPA1). Icilin inhibits transient receptor potential cation channel subfamily M member 8 (TRPM8) and modulates calcium release. Icilin also suppresses transient receptor potential vanilloid subtype 3 (TRPV3).
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Inhibition of TRPM8 by icilin distinct from desensitization induced by menthol and menthol derivatives
Kuhn FJP, et al.
The Journal of Biological Chemistry, 284(7), 4102-4111 (2009)
Warm-sensitive neurons that control body temperature
Tan CL, et al.
Cell, 167(1), 47-59 (2016)
Supercooling agent icilin blocks a warmth-sensing ion channel TRPV3
Sherkheli MA, et al.
TheScientificWorldJournal, 2012(6), 859-869 (2012)
Alexander Lucius et al.
Cellular signalling, 28(3), 136-147 (2015-12-23)
3-Iodothyronamine (3T1AM) is an endogenous thyroid hormone metabolite that interacts with the human trace amine-associated receptor 1 (hTAAR1), a G-protein-coupled receptor, to induce numerous physiological responses including dose-dependent body temperature lowering in rodents. 3T1AM also directly activates cold-sensitive transient receptor
Dimitra Gkika et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 34(6), 7483-7499 (2020-04-12)
Recent studies have revealed gender differences in cold perception, and pointed to a possible direct action of testosterone (TST) on the cold-activated TRPM8 (Transient Receptor Potential Melastatin Member 8) channel. However, the mechanisms by which TST influences TRPM8-mediated sensory functions
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