IcilinA potent agonist of the TRPM8 and ENaCδ ion channels

Icilin (CAS 36945-98-9)

Icilin | CAS 36945-98-9 is rated 5.0 out of 5 by 1.
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Synonym: AG 3-5; 3,6-Dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-2(1H)-pyrimidinone
Application: A potent agonist of the TRPM8 and ENaCδ ion channels
CAS Number: 36945-98-9
Purity: ≥97%
Molecular Weight: 311.3
Molecular Formula: C16H13N3O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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Icilin is a small molecule agonist of the TRPM8 (transient receptor potential M8) ion channel, a non-selective Ca2+ channel which depolarizes somatosensory neurons in response to cold temperature. Though Icilin is structurally unrelated to Menthol (sc-202705), both compounds activate the TRPM8 receptor to produce cold sensation, and Icilin is ~200-fold more potent than Menthol in this action. Sensitization of TRPM8 by Icilin exhibits a significant temporal delay and a dependence upon extracellular Ca2+, disparate from the immediately-activating, Ca2+ independent action of Menthol. This variable sensitization of the TRPM8 indicates a unique modular activation mechanism depending on the presence of co-agonist input, and Icilin has been employed as a tool for elucidation of TRP ion channel functionality. Icilin regulates Na+ homeostasis in cells across the epithelia through the amiloride-sensitive epithelial Na+ channel. Icilin is an activator of ANKTM1. Icilin is a inhibitor of TRPV3.


References

1. Wei, E.T., et al. 1983. J. Pharm. Pharmacol. 35: 110-112. PMID: 6131976
2. McKemy, D.D., et al. 2002. Nature. 416: 52-58. PMID: 11882888
3. Story, G.M., et al. 2003. Cell. 112: 819-829. PMID: 12654248
4. Chuang, H.H., et al. 2004. Neuron. 43: 859-869. PMID: 15363396
5. Yamamura, H., et al. 2005. Mol. Pharmacol. 68: 1142-1147. PMID: 16033954
6. Rawls, S.M., et al. 2007. Eur. J. Pharmacol. 575: 103-104. PMID: 17765220

Physical State :
Solid
Solubility :
Soluble in water (0.1 mg/ml) at 25° C, DMSO:PBS pH 7.2(1:5), DMSO (50 mg/ml), and DMF.
Storage :
Store at room temperature
Melting Point :
229° C
Boiling Point :
~594.8° C at 760 mmHg (Predicted)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.67 (Predicted)
IC50 :
TRPM8: IC50 = 0.2 µM; cold menthol receptor 1 : IC50 = 0.36 µM; currents in TRPM8 expressing HEK 293 cells: EC5050 = 0.36 mM
pK Values :
pKa: 9.94 (Predicted), pKb: 0.94 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
UW7397500
PubChem CID :
161930
MDL Number :
MFCD01689072
SMILES :
C1C=C(NC(=O)N1C2=CC=CC=C2O)C3=CC(=CC=C3)[N+](=O)[O-]

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Icilin  Product Citations

See how others have used Icilin. Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 18802106  Prasad, P. et al. 2008. J. Immunol. 181: 5024-5034.

PMID: # 15363396  Chuang, HH. et al. 2004. Neuron. 43: 859-869.

PMID: # 31654626  Biochem. Pharmacol. 113678.

Citations 1 to 3 of 3 total
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Rated 5 out of 5 by from Chuang Chuang, et. al. (PubMed ID 15363396) found that icilin showed very little agonist activity when calcium is absent, but does not affect its potency (concentrations from 10 to 100 M were tested with no change in outcome). Upon adding calcium, icilin's efficacy recovered. Tests were performed via Voltage-clamp recordings from TRPM8 expressing Xenopus oocytes or HEK293 cells. -SCBT Publication Review
Date published: 2015-01-09
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