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

• ChemBase ID: 127039
• Molecular Formular: C20H26N2O2
• Molecular Mass: 326.43264
• Monoisotopic Mass: 326.19942808
• SMILES: O(c1cc2c(nccc2[C@@H](O)[C@H]2N3CC[C@@H](C2)[C@@H](CC)C3)cc1)C
• Canonical SMILES: CC[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](c1ccnc2c1cc(OC)cc2)O
• InChI: InChI=1S/C20H26N2O2/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/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1
• InChIKey: LJOQGZACKSYWCH-WZBLMQSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
• IUPAC Traditional name: dihydroquinine
• Synonyms: Dihydroquinine; Dihydroquinine; Hydroquinine; 二氢奎宁; 氢化奎宁

Database IDs

• CAS Number: 522-66-7
• EC Number: 208-334-0
• MDL Number: MFCD00151107
• Beilstein Number: 91444
• PubChem SID: 24878406; 162221362; 24860494
• PubChem CID: 121515
• Chemspider ID: 108426
• Wikipedia Title: Dihydroquinine

CALCULATED PROPERTIES

• Acid pKa: 13.89212
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.47483543
• LogD (pH = 7.4): 1.0415924
• Log P: 2.817452
• Molar Refractivity: 94.6495 cm^3
• Polarizability: 38.58629 Å^3
• Polar Surface Area: 45.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 168-176 °C; 168-176 °C(lit.); 173-175 °C
• Optical Rotation: [α]20/D -143±5°, c = 1% in ethanol (dry matter); [α]25/D -148°, c = 1 in ethanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

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

Product Information

• Purity: ≥95.0% (sum of enantiomers, HPLC); 98%
• Grade: purum
• Loss on Drying: ≤1% loss on drying, 110 °C
• Empirical Formula (Hill Notation): C20H26N2O2

DETAILS

Sigma Aldrich - 337714

Packaging
5 g in glass bottle