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

• ChemBase ID: 126601
• Molecular Formular: C19H22N2O
• Molecular Mass: 294.39078
• Monoisotopic Mass: 294.17321333
• SMILES: n1c2c(cccc2)c(cc1)[C@@H](O)[C@H]1N2CC[C@@H](C1)[C@@H](C=C)C2
• 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-KODHJQJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
• IUPAC Traditional name: cinchonidine
• Synonyms: Cinchonidine; (-)-Cinchonidine; Cinchonidine; 金鸡尼丁; 辛可尼丁

Database IDs

• CAS Number: 485-71-2
• EC Number: 207-622-3
• MDL Number: MFCD00006783
• Beilstein Number: 89690
• PubChem SID: 24893015; 24856544; 162220931
• PubChem CID: 101744
• CHEBI ID: 3703
• CHEMBL: 533841
• Chemspider ID: 91930
• Unique Ingredient Identifier: 1U622LRA8Z
• Wikipedia Title: Cinchonidine

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: slightly soluble 0,25 g·l^-1 (20 °C) in water
• Melting Point: ~205 °C; 204-206 °C(lit.); 205 °C
• Boiling Point: 464.5°C
• Density: 1.2 g/mL
• Optical Rotation: [α]20/D -106±4°, c = 1% in ethanol; [α]23/D -109.2°, c = 1.5 in ethanol

Safety Information

• RTECS: GD2975000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-22-43-48/22; R22
• Safety Statements: 36/37; S2, S45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317-H361d-H373
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... CYP2D6(1565)
• Target Organ: Heart, Immune system

Product Information

• Purity: ≥98.0% (dried material, NT); 96%; 98%
• Grade: purum
• Ignition Residue: ≤0.1%
• Impurities: ≤15% hydrocinchonine (HPLC); ≤5% quinine (HPLC)
• Loss on Drying: ≤1% loss on drying, 110 °C
• Empirical Formula (Hill Notation): C19H22N2O

DETAILS

Sigma Aldrich - C80407

Packaging
10, 100 g in glass bottle