WS-12

WS-12
Names
	Preferred IUPAC name (1R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(propan-2-yl)cyclohexane-1-carboxamide
Identifiers
CAS Number	68489-09-8;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2441929;
ChemSpider	9441255;
EC Number	700-232-9;
PubChem CID	11266244;
UNII	1L7BVT4Z4Z;
CompTox Dashboard (EPA)	DTXSID10460636 ;
	InChI InChI=1S/C18H27NO2/c1-12(2)16-10-5-13(3)11-17(16)18(20)19-14-6-8-15(21-4)9-7-14/h6-9,12-13,16-17H,5,10-11H2,1-4H3,(H,19,20)/t13-,16+,17-/m1/s1 Key: HNSGVPAAXJJOPQ-XOKHGSTOSA-N;
	SMILES C[C@@H]1CC[C@H]([C@@H](C1)C(=O)NC2=CC=C(C=C2)OC)C(C)C;
Properties
Chemical formula	C18H27NO2
Molar mass	289.419 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

WS-12 is a chemical compound that acts as a potent and selective activator of the TRPM8 calcium channel, which is responsible for the sensation of coldness produced by menthol. It is slightly less potent as a TRPM8 activator compared to icilin, but is much more selective for TRPM8 over related calcium channels. It produces analgesic and antiinflammatory effects in animal models with similar efficacy to menthol and a reduced side effect profile.^[1]^[2]^[3]^[4]^[5]

References

↑ Bödding M, Wissenbach U, Flockerzi V (December 2007). "Characterisation of TRPM8 as a pharmacophore receptor". Cell Calcium. 42 (6): 618–28. doi:10.1016/j.ceca.2007.03.005. PMID 17517434.
↑ Sherkheli MA, Vogt-Eisele AK, Bura D, Beltrán Márques LR, Gisselmann G, Hatt H. "Characterization of selective TRPM8 ligands and their structure activity response (S.A.R) relationship". Journal of Pharmacy & Pharmaceutical Sciences. 13 (2): 242–53. doi:10.18433/j3n88n. PMID 20816009.
↑ Liu B, Fan L, Balakrishna S, Sui A, Morris JB, Jordt SE (October 2013). "TRPM8 is the principal mediator of menthol-induced analgesia of acute and inflammatory pain". Pain. 154 (10): 2169–77. doi:10.1016/j.pain.2013.06.043. PMC 3778045. PMID 23820004.
↑ Peixoto-Neves D, Soni H, Adebiyi A (November 2018). "Oxidant-induced increase in norepinephrine secretion from PC12 cells is dependent on TRPM8 channel-mediated intracellular calcium elevation". Biochemical and Biophysical Research Communications. 506 (3): 709–715. doi:10.1016/j.bbrc.2018.10.120. PMID 30376995.
↑ Yin Y, Le SC, Hsu AL, Borgnia MJ, Yang H, Lee SY (March 2019). "Structural basis of cooling agent and lipid sensing by the cold-activated TRPM8 channel". Science. 363 (6430). doi:10.1126/science.aav9334. PMC 6478609. PMID 30733385.

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[1] Bödding M, Wissenbach U, Flockerzi V (December 2007). "Characterisation of TRPM8 as a pharmacophore receptor". Cell Calcium. 42 (6): 618–28. doi:10.1016/j.ceca.2007.03.005. PMID 17517434.

[2] Sherkheli MA, Vogt-Eisele AK, Bura D, Beltrán Márques LR, Gisselmann G, Hatt H. "Characterization of selective TRPM8 ligands and their structure activity response (S.A.R) relationship". Journal of Pharmacy & Pharmaceutical Sciences. 13 (2): 242–53. doi:10.18433/j3n88n. PMID 20816009.

[3] Liu B, Fan L, Balakrishna S, Sui A, Morris JB, Jordt SE (October 2013). "TRPM8 is the principal mediator of menthol-induced analgesia of acute and inflammatory pain". Pain. 154 (10): 2169–77. doi:10.1016/j.pain.2013.06.043. PMC 3778045. PMID 23820004.

[4] Peixoto-Neves D, Soni H, Adebiyi A (November 2018). "Oxidant-induced increase in norepinephrine secretion from PC12 cells is dependent on TRPM8 channel-mediated intracellular calcium elevation". Biochemical and Biophysical Research Communications. 506 (3): 709–715. doi:10.1016/j.bbrc.2018.10.120. PMID 30376995.

[5] Yin Y, Le SC, Hsu AL, Borgnia MJ, Yang H, Lee SY (March 2019). "Structural basis of cooling agent and lipid sensing by the cold-activated TRPM8 channel". Science. 363 (6430). doi:10.1126/science.aav9334. PMC 6478609. PMID 30733385.

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