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

• ChemBase ID: 149338
• Molecular Formular: C19H22N2O
• Molecular Mass: 294.39078
• Monoisotopic Mass: 294.17321333
• SMILES: C=C[C@H]1CN2CCC1C[C@@H]2[C@H](c1ccnc2c1cccc2)O
• Canonical SMILES: C=C[C@H]1CN2CCC1C[C@@H]2[C@H](c1ccnc2c1cccc2)O
• InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14?,18+,19-/m0/s1
• InChIKey: KMPWYEUPVWOPIM-FGVBSWQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
• IUPAC Traditional name: (S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
• Synonyms: Cinchonan-9(S)-ol monohydrochloride; Cinchonine monohydrochloride hydrate; (9S)-Cinchonan-9-ol; (+)-Cinchonine; (8R,9S)-Cinchonine; NSC 6176; d-Cinchonine; Cinchonine; 弱金鸡纳碱 单盐酸盐; 辛可宁 单盐酸盐 水合物

Database IDs

• CAS Number: 118-10-5; 206986-88-1
• MDL Number: MFCD00191936
• Beilstein Number: 5784953
• PubChem SID: 162243505; 24866328
• PubChem CID: 2724372

CALCULATED PROPERTIES

• Acid pKa: 13.8773155
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.60487753
• LogD (pH = 7.4): 0.92435837
• Log P: 2.6711352
• Molar Refractivity: 88.2304 cm^3
• Polarizability: 35.8717 Å^3
• Polar Surface Area: 36.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 208-218 °C(lit.)
• Optical Rotation: [α]20/D +101±2°, c = 1% in chloroform; [α]20/D +101°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (HPLC); 99%
• Grade: puriss.
• Impurities: ~5% water
• Empirical Formula (Hill Notation): C19H22N2O · HCl · xH2O

DETAILS

Sigma Aldrich - 420328

Packaging
50 mg in glass bottle

Sigma Aldrich - 27390

Application
Specially purified cinchonine monohydrochloride with minimal contamination by dihydrocinchonine
Preparation Note
produced from 27369

Toronto Research Chemicals - C441935

Stereomeric with Cinchonidine (C441925). Antimalarial.

REFERENCES

• Litchfield, J., et al.: J. Pharm. Exp. Ther., 96, 99 (1949)
• Trager, W., et al.: Science, 193, 673 (1949)
• Panisko, D., et al.: Drugs, 39, 160 (1949)
• Karle, J., et al.: Antimicrob. Agents Chemother., 36, 1538 (1949)