(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol; sulfuric acid

• ChemBase ID: 177287
• Molecular Formular: C20H26N2O6S
• Molecular Mass: 422.49524
• Monoisotopic Mass: 422.15115756
• SMILES: c1(ccc2c(c1)c(ccn2)[C@H]([C@H]1N2CC[C@@H](C1)[C@H](C2)C=C)O)OC.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](c1ccnc2c1cc(OC)cc2)O
• InChI: InChI=1S/C20H24N2O2.H2O4S/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;1-5(2,3)4/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4)/t13-,14-,19-,20+;/m0./s1
• InChIKey: AKYHKWQPZHDOBW-DSXUQNDKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol; sulfuric acid
• IUPAC Traditional name: quinine; sulfuric acid
• Synonyms: (8α,9R)-6'-Methoxycinchonan-9-ol Sulfate Hydrate; (-)-Quinine Sulfate Dihydrate; Quinine Sulfate Dihydrate

Database IDs

• CAS Number: 6119-70-6
• PubChem SID: 164233197
• PubChem CID: 11949689

CALCULATED PROPERTIES

• Acid pKa: 13.892048
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.7213722
• LogD (pH = 7.4): 0.863951
• Log P: 2.513464
• Molar Refractivity: 94.6936 cm^3
• Polarizability: 38.350784 Å^3
• Polar Surface Area: 45.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform (Sparingly); DMSO; Methanol
• Apperance: White Solid
• Melting Point: 211-213°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - Q694001

Primary alkaloid of various species of Cinchona (Rubiaceae). Optical isomer of Quinidine. Antimalarial; muscle relaxant (skeletal).

REFERENCES

• Muhtadi, F.J., et al.: Anal. Profiles Drug Subs., 12, 547 (1983)
• Kremsner, P.G., et al.: J. Infect. Dis., 169, 467 (1983)