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

• ChemBase ID: 146558
• Molecular Formular: C19H22N2O
• Molecular Mass: 294.39078
• Monoisotopic Mass: 294.17321333
• SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cccc2)O
• Canonical SMILES: C=C[C@H]1CN2CC[C@H]1C[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-QAMTZSDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
• IUPAC Traditional name: (+)-cinconine
• Synonyms: Cinchonine; Cinchonine monohydrochloride dihydrate; (+)-Cinchonine; (+)-Quinolin-4-yl(5-vinylquinuclidin-2-yl)methanol; 辛可宁; 辛可宁 单盐酸盐 二水合物; (+)-辛可宁

Database IDs

• CAS Number: 118-10-5
• EC Number: 204-234-6
• MDL Number: MFCD00064372
• Beilstein Number: 89689
• PubChem SID: 24856547; 162240752; 24888435
• PubChem CID: 90454

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: 255-261 °C; 258-260 °C(lit.); 260-263 °C
• Optical Rotation: [α]20/D +225±5°, c = 0.5% in ethanol; [α]20/D +229±4°, c = 0.5% in ethanol; [α]23/D +228°, c = 0.5 in ethanol

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/22
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H332
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... CYP2D6(1565)

Product Information

• Purity: ≥98.0% (NT); ≥99.0% (HPLC/NT); 85%; 98%
• Grade: puriss.
• Impurities: ~15% dihydrocinchonine (HPLC)
• Quality: crystallized
• Empirical Formula (Hill Notation): C19H22N2O

DETAILS

Sigma Aldrich - 27370

Packaging
25, 100 g in poly bottle

Sigma Aldrich - 857270

Other Notes
remainder dihydrocinchonine
Packaging
25, 100 g in poly bottle

Sigma Aldrich - 27369

Application
Specially purified cinchonine with minimal contamination by dihydrocinchonine