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

• ChemBase ID: 72931
• Molecular Formular: C19H22N2O
• Molecular Mass: 294.39078
• Monoisotopic Mass: 294.17321333
• SMILES: c1c2c(ccc1)nccc2[C@H]([C@H]1N2CCC(C1)[C@H](C2)C=C)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-YNRGSOABSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
• IUPAC Traditional name: (8a α,9R)-cinchonan-9-ol
• Synonyms: Cinchonidine; (8α,9R)-Cinchonan-9-ol; (-)-Cinchonidine; (8S,9R)-Cinchonidine; Cinchovatine; NSC 5364; α-Quinidine

Database IDs

• CAS Number: 485-71-2
• PubChem SID: 162037851
• PubChem CID: 443155

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

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 198-200°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2282

Research Area: Infection
Biological Activity:
Cinchonidine is an alkaloid used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo-enantiomer of cinchonine. [1] Cinchonidine beta-resorcylate was active; all mice were cured at 1 mmol/kg and the mean survival time was 13.8 +/- 2.4 days after a subcutaneous treatment at 0.5 mmol/kg in a single dose. In the series of acridines, (N-alpha, sigma-dioxopentyl)-5-amino-1,2,3,4-tetrahydroacridine cured all mice at 50 mumol/kg under the same conditions. The maximum tolerated doses in mice ranged from 100 to 150 mumol/kg for these acridine derivatives. [2]

Toronto Research Chemicals - C441925

Occurs in most varieties of Cinchona bark. It is stereoisomeric with Cinchonine. Antimalarial.

REFERENCES

• Loiseau PM et al. Trop Med Int Health. 1996 Jun;1(3):379-84.
• 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)