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I9532

Sigma-Aldrich

Icilin

≥97% (HPLC), 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:
36945-98-9
Molecular Weight:
311.29
MDL number:
MFCD01689072
UNSPSC Code:
12352200
PubChem Substance ID:
24277906
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

solid

color

yellow

solubility

DMSO: 15 mg/mL

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

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).

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Supercooling agent icilin blocks a warmth-sensing ion channel TRPV3
Sherkheli MA, et al.
TheScientificWorldJournal, 2012(6), 859-869 (2012)
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)
The super-cooling agent icilin reveals a mechanism of coincidence detection by a temperature-sensitive TRP channel
Chuang HH, et al.
Neuron, 43(6), 859-869 (2004)
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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