| Identification | Back Directory | [Name]
WS 12 | [CAS]
68489-09-8 | [Synonyms]
WS 12
Cooling agent WS12
N-(4-Methoxyphenyl)-p-menthane-3-carboxamide
N- (4- methoxy phenyl) - menthol -3- carboxylase
N-(4-Methoxyphenyl)-p-menthane-3-carboxamide(WS-12)
(2S,5R)-2-Isopropyl-N-(4-methoxyphenyl)-5-methylcyclohexanecarboximide
Cyclohexanecarboxamide, N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-
(1R,2S,5R)-2-Isopropyl-N-(4-methoxyphenyl)-5-methylcyclohexane-1-carboxamide
(1R*,2S*)-N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide
(1R,2S,5R)-N-(4-METHOXYPHENYL)-5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANECARBOXAMIDE
CyclohexanecarboxaMide, N-(4-Methoxyphenyl)-5-Methyl-2-(1-Methylethyl)-, (1R,2S,5R)- | [EINECS(EC#)]
256-974-4 | [Molecular Formula]
C18H27NO2 | [MDL Number]
MFCD11100191 | [MOL File]
68489-09-8.mol | [Molecular Weight]
289.416 |
| Hazard Information | Back Directory | [Description]
WS-12 is an agonist of transient receptor potential melastatin 8 (TRPM8). It induces currents in Xenopus oocytes expressing mouse TRPM8 (EC50 = 12 μM) and is selective for TRPM8 over transient receptor potential vanilloid 1-4 (TRPV1-4) and transient receptor potential ankyrin 1 (TRPA1) at 1 mM. WS-12 (6 nmol, i.c.v.) reduces nocifensive behavior induced by capsaicin in wild-type, but not Trpm8-/-, mice. It induces analgesia in the hot plate test, an effect that can be reversed by the opioid receptor antagonist naloxone, in mice. | [Chemical Properties]
WS 12 is a odorless white crystalline solid,mp 178 °C, displaying
a strong initial cooling effect and a long-lastingness. It is used particularly is oral
care flavors. | [Uses]
Cooling agent. High-affinity TRPM8 (cold menthol receptor 1; CMR1) agonist. Has an EC50 value ~2'000 times lower than that of (-)-menthol . | [Trade name]
Winsense WS-12 (Renessenz) | [Biological Activity]
Potent TRPM8 agonist that acts as a cooling agent (EC 50 = 193 nM). | [Biochem/physiol Actions]
WS-12 is a menthol derivative, that shows a specific binding affinity towards TRPM8 (transient receptor potential cation channel subfamily M member 8) receptor. TRPM8 is associated with prostate cancer and thus, WS-12 might be useful in reducing the progression of cancer. | [storage]
Store at -20°C | [References]
[1] SHERKHELI MA. Menthol derivative WS-12 selectively activates transient receptor potential melastatin-8 (TRPM8) ion channels.[J]. Pakistan journal of pharmaceutical sciences, 2008, 21 4: 370-378.
[2] BOYI LIU . TRPM8 is the principal mediator of menthol-induced analgesia of acute and inflammatory pain[J]. PAIN?, 2013, 154 10: Pages 2169-2177. DOI: 10.1016/j.pain.2013.06.043 |
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