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Dokumente

W0519

Sigma-Aldrich

WS-12

≥98% (HPLC), powder

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C18H27NO2
CAS-Nummer:
68489-09-8
Molekulargewicht:
289.41
MDL-Nummer:
MFCD11100191
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329830423
NACRES:
NA.25

Assay

≥98% (HPLC)

Form

powder

Farbe

white to off-white

Löslichkeit

DMSO: >20 mg/mL

Lagertemp.

−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

InChIKey

HNSGVPAAXJJOPQ-NVPAJSRCSA-N

Biochem./physiol. Wirkung

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.

Piktogramme

Environment
GHS09

Signalwort

Warning

H-Sätze

H410

Gefahreneinstufungen

Aquatic Acute 1 - Aquatic Chronic 1

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

TRP Channels, 378-378 (2016)
Norihiro Suzuki et al.
Molecular nutrition & food research, e2000853-e2000853 (2020-11-15)
Peppermint is traditionally used as an antigalactagogue in breastfeeding women. However, the suppressive mechanism remains unclear. The authors investigate whether and how peppermint influences milk production at the cellular and molecular levels. A lactating mammary epithelial cell (MEC) culture model
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
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