4-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]-6-methoxyquinolin-1-ium-1-olate

• ChemBase ID: 177281
• Molecular Formular: C20H24N2O3
• Molecular Mass: 340.41616
• Monoisotopic Mass: 340.17869264
• SMILES: c1(ccc2c(c1)c(cc[n+]2[O-])[C@@H]([C@@H]1N2CC[C@@H](C1)[C@H](C2)C=C)O)OC
• Canonical SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](c1cc[n+](c2c1cc(OC)cc2)[O-])O
• InChI: InChI=1S/C20H24N2O3/c1-3-13-12-21-8-6-14(13)10-19(21)20(23)16-7-9-22(24)18-5-4-15(25-2)11-17(16)18/h3-5,7,9,11,13-14,19-20,23H,1,6,8,10,12H2,2H3/t13-,14-,19+,20-/m0/s1
• InChIKey: GBBIANHNFAPFOH-LHHVKLHASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]-6-methoxyquinolin-1-ium-1-olate
• IUPAC Traditional name: 4-[(S)-[(1S,2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]-6-methoxyquinolin-1-ium-1-olate
• Synonyms: 6'-Methoxy-cinchonan-9-ol 1'-Oxide; Quinidine 1'-N-oxide; Quinidine 1'-oxide; Quinidine N'-oxide; Quinidine ar-N-oxide; ICQ 17; Quinidine 1'-Oxide

Database IDs

• CAS Number: 115730-97-7
• PubChem SID: 164233191
• PubChem CID: 40493389

CALCULATED PROPERTIES

• Log P: 1.4144448
• Molar Refractivity: 98.6011 cm^3
• Polarizability: 38.78634 Å^3
• Polar Surface Area: 58.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 13.805381
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.7064064
• LogD (pH = 7.4): -0.051033214

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 173-176°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - Q685010

A metabolite of Quinidine.

REFERENCES

• Small, D.L., J. Chem. Med., 22,1014 (1979)
• Guentert, T.W., et al.: Eur. J. Drug Metab. Pharmacokinet., 7, 31 (1979)
• Chang, Y.F., et al.: Neurochem. Res., 13, 455 (1979)