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

• ChemBase ID: 177286
• Molecular Formular: C20H24N2O2
• Molecular Mass: 324.41676
• Monoisotopic Mass: 324.18377802
• SMILES: c1(ccc2c(c1)c(ccn2)[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](c1ccnc2c1cc(OC)cc2)O
• InChI: InChI=1S/C20H24N2O2/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/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1
• InChIKey: LOUPRKONTZGTKE-WZBLMQSHSA-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
• IUPAC Traditional name: quinine
• Synonyms: (8α,9R)-6’-Methoxycinchonan-9-ol; (-)-Quinine; (8S,9R)-Quinine; (R)-(-)-Quinine; 6'-Methoxycinchonidine; Chinine; NSC 192949; Quinine; Quinine

Database IDs

• CAS Number: 130-95-0
• PubChem SID: 164233196
• PubChem CID: 3034034

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; Ethyl Acetate
• Apperance: Powder; White to Off-White Solid
• Melting Point: 174-176°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - Q694000

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)