(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl](2R)-piperidin-2-ylmethanol hydrochloride

• ChemBase ID: 153843
• Molecular Formular: C17H17ClF6N2O
• Molecular Mass: 414.7730992
• Monoisotopic Mass: 414.09336017
• SMILES: c1cc2c(cc(nc2c(c1)C(F)(F)F)C(F)(F)F)[C@@H]([C@H]1CCCCN1)O.Cl
• Canonical SMILES: O[C@@H](c1cc(nc2c1cccc2C(F)(F)F)C(F)(F)F)[C@H]1CCCCN1.Cl
• InChI: InChI=1S/C17H16F6N2O.ClH/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11;/h3-5,8,12,15,24,26H,1-2,6-7H2;1H/t12-,15+;/m1./s1
• InChIKey: WESWYMRNZNDGBX-YLCXCWDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl](2R)-piperidin-2-ylmethanol hydrochloride
• IUPAC Traditional name: (-)-mefloquine hydrochloride
• Synonyms: (AS)-rel-a-(2R)-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol monohydrochloride; Mefloquine hydrochloride; (αS)-rel-α-(2R)-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol; (+/-)-Mefloquine Hydrochloride; Loriam; Mefloquin Hydrochloride; Mefloquine Hydrochloride; NSC 157387; Ro 21-5998/001; WR 142490; Mefloquine Hydrochloride

Database IDs

• CAS Number: 51773-92-3
• EC Number: 257-412-0
• MDL Number: MFCD00797519
• PubChem SID: 24724536; 162247982
• PubChem CID: 65329

CALCULATED PROPERTIES

• Acid pKa: 13.785841
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.94418555
• LogD (pH = 7.4): 2.0721047
• Log P: 4.1105947
• Molar Refractivity: 82.5774 cm^3
• Polarizability: 31.66879 Å^3
• Polar Surface Area: 45.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble38 mg/mL; H2O: insoluble; Methanol
• Apperance: white powder; White Solid
• Melting Point: 250-254°C (dec.)

Safety Information

• Storage Condition: Refrigerator
• RTECS: VC0308000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98% (HPLC); 95+%
• Empirical Formula (Hill Notation): C17H17ClF6N2O

DETAILS

Sigma Aldrich - M2319

Biochem/physiol Actions
Blocker of gap junction channels Cx36 and Cx50.

Toronto Research Chemicals - M207050

Quinoline methanol antimalarial agent.

REFERENCES

• Carroll, F.I., et al.: J. Med. Chem., 17, 210 (1974)
• Davidson, M.W., et al.: J. Med. Chem., 20, 1117 (1974)
• Brown, R.E., et al.: Life Sci., et al.: 25, 1857 (1974)
• Lim, P., et al.: Anal. Profiles Drug Subs., 14, 157 (1974)