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I9532

Icilin

Name: Icilin
Brand: SIGMA

≥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.

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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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)

Supercooling agent icilin blocks a warmth-sensing ion channel TRPV3

Sherkheli MA, et al.

TheScientificWorldJournal, 2012(6), 859-869 (2012)

Warm-sensitive neurons that control body temperature

Tan CL, et al.

Cell, 167(1), 47-59 (2016)

Strongylocentrotus nudos Egg Polysaccharide induces autophagy and apoptosis in leukaemia cells by regulating mitochondrial function.

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

3-Iodothyronamine increases transient receptor potential melastatin channel 8 (TRPM8) activity in immortalized human corneal epithelial cells.

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

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