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W0519

Sigma-Aldrich

WS-12

≥98% (HPLC), powder

Sinónimos:

(1R,2S,5R)-2-Isopropyl-N-(4-methoxyphenyl)-5-methylcyclohexanecarboxamide

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About This Item

Fórmula empírica (notación de Hill):
C18H27NO2
Número de CAS:
68489-09-8
Peso molecular:
289.41
MDL number:
MFCD11100191
UNSPSC Code:
12352200
PubChem Substance ID:
329830423
NACRES:
NA.25

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

−20°C

SMILES string

COc1ccc(NC(=O)C2C[C@H](C)CC[C@H]2C(C)C)cc1

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

InChI key

HNSGVPAAXJJOPQ-NVPAJSRCSA-N

Biochem/physiol Actions

WS-12 is a high-affinity, selective TRPM8 (cold menthol receptor 1; CMR1) agonist. TRPM8 agonists induce a cooling sensation in sensory neurons and produce profound, mechanistically novel analgesia in chronic pain states such as neuropathic pain.
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.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
047M4721V
016M4733V
073M4716V
072M4729V
101M4708V

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TRP Channels, 378-378 (2016)
Ying Yin et al.
Science (New York, N.Y.), 363(6430) (2019-02-09)
Transient receptor potential melastatin member 8 (TRPM8) is a calcium ion (Ca2+)-permeable cation channel that serves as the primary cold and menthol sensor in humans. Activation of TRPM8 by cooling compounds relies on allosteric actions of agonist and membrane lipid
Mária Dux et al.
European journal of pain (London, England), 24(2), 383-397 (2019-10-30)
The α1 -adrenoceptor agonist, phenylephrine, is used at high concentrations as a mydriatic agent and for the treatment of nasal congestion. Among its adverse side-effects transient burning sensations are reported indicating activation of the trigeminal nociceptive system. Neuropeptide release, calcium
Tusar K Acharya et al.
Cell biology international, 45(1), 198-210 (2020-10-23)
The transient receptor potential melastatin 8 (TRPM8) is an ion channel that has been widely studied as a cold-sensitive nociceptor. However, its importance in nonneuronal cells is mostly unexplored. Here, we describe the presence and functional significance of endogenous TRPM8
Xuming Zhang
Cell reports, 27(12), 3672-3683 (2019-06-20)
Activation of Gαq-coupled receptors by inflammatory mediators inhibits cold-sensing TRPM8 channels, aggravating pain and inflammation. Both Gαq and the downstream hydrolysis of phosphatidylinositol 4, 5-bisphosphate (PIP2) inhibit TRPM8. Here, I demonstrate that direct Gαq gating is essential for both the
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