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

• ChemBase ID: 177283
• Molecular Formular: C20H24N2O3
• Molecular Mass: 340.41616
• Monoisotopic Mass: 340.17869264
• SMILES: c1(ccc2c(c1)c(ccn2)[C@@H]([C@@H]1[N@+]2(CC[C@@H](C1)[C@H](C2)C=C)[O-])O)OC
• Canonical SMILES: C=C[C@H]1C[N@+]2([O-])CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cc(OC)cc2)O
• InChI: InChI=1S/C20H24N2O3/c1-3-13-12-22(24)9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(25-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20-,22+/m0/s1
• InChIKey: WVDIZKMXQMCCAA-ROCUERRRSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 70116-00-6
• PubChem SID: 164233193
• PubChem CID: 23622544

CALCULATED PROPERTIES

• Acid pKa: 13.320991
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.3496977
• LogD (pH = 7.4): 1.3885671
• Log P: 1.3890887
• Molar Refractivity: 96.7385 cm^3
• Polarizability: 38.44737 Å^3
• Polar Surface Area: 69.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 145-149°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - Q685015

A Quinidine metabolite.

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)