(2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(propan-2-yl)cyclohexane-1-carboxamide

• ChemBase ID: 154398
• Molecular Formular: C18H27NO2
• Molecular Mass: 289.41248
• Monoisotopic Mass: 289.20417911
• SMILES: C[C@@H]1CC[C@H](C(C1)C(=O)Nc1ccc(cc1)OC)C(C)C
• Canonical SMILES: COc1ccc(cc1)NC(=O)C1C[C@H](C)CC[C@H]1C(C)C
• 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
• InChIKey: HNSGVPAAXJJOPQ-WBTZKQGOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(propan-2-yl)cyclohexane-1-carboxamide
• IUPAC Traditional name: (2S,5R)-2-isopropyl-N-(4-methoxyphenyl)-5-methylcyclohexane-1-carboxamide
• Synonyms: (2S,5R)-2-Isopropyl-N-(4-methoxyphenyl)-5-methylcyclohexanecarboximide; WS-12

Database IDs

• PubChem SID: 162248537
• PubChem CID: 71311855

CALCULATED PROPERTIES

• Acid pKa: 14.585513
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.472413
• LogD (pH = 7.4): 4.472413
• Log P: 4.472413
• Molar Refractivity: 86.8332 cm^3
• Polarizability: 33.57438 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50
• Safety Statements: 53-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H410
• GHS Precautionary statements: P273-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H27NO2

DETAILS

Sigma Aldrich - W0519

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.1