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)
Chong Wang et al.
Journal of cellular and molecular medicine (2020-12-09)
In this study, we investigated the ability of the Polysaccharide from the Eggs of Strongylocentrotus nudus (SEP) to regulate cellular autophagy and apoptosis in leukaemia cells. Human acute myeloid leukaemia (AML) cells (HL60) and murine AML cells (L1210) treated with
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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