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

• ChemBase ID: 130392
• Molecular Formular: C20H24N2O2
• Molecular Mass: 324.41676
• Monoisotopic Mass: 324.18377802
• SMILES: O(c1cc2c(nccc2[C@@H](O)[C@H]2N3CC[C@@H](C2)[C@@H](C=C)C3)cc1)C
• Canonical SMILES: C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](c1ccnc2c1cc(OC)cc2)O
• InChI: InChI=1S/C20H24N2O2/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/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1
• InChIKey: LOUPRKONTZGTKE-WZBLMQSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
• IUPAC Traditional name: quinine
• Brand Name: Qualaquin
• Synonyms: Quinine; Quinine; 奎宁

Database IDs

• CAS Number: 130-95-0
• EC Number: 205-003-2
• MDL Number: MFCD00198096
• Beilstein Number: 91867
• PubChem SID: 24848751; 24853550; 162224671
• PubChem CID: 8549; 3034034
• CHEBI ID: 15854
• ATC CODE: M09AA01; P01BC01
• CHEMBL: 170
• Chemspider ID: 84989
• DrugBank ID: DB00468
• IUPHAR ligand ID: 2510
• KEGG ID: D08460
• Unique Ingredient Identifier: A7V27PHC7A
• Wikipedia Title: Quinine
• Medline Plus: a682322

CALCULATED PROPERTIES

• Acid pKa: 13.892048
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.7213722
• LogD (pH = 7.4): 0.863951
• Log P: 2.513464
• Molar Refractivity: 94.6936 cm^3
• Polarizability: 38.350784 Å^3
• Polar Surface Area: 45.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 173-175 °C(lit.); 177°C (350.6°F)
• Optical Rotation: [α]20/D -126±5°, c = 1% in chloroform; [α]25/D -165°, c = 2 in ethanol
• Fluorescence: λex 347 nm; λem 448 nm in 0.5 M sulfuric acid

Safety Information

• RTECS: VA6020000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Admin Routes: Oral, intravenous
• Bioavailability: 76 to 88%
• Excretion: Renal (20%)
• Half Life: ~18 hours
• Metabolism: Hepatic (mostly CYP3A4 and CYP2C19-mediated)
• Protein Bound: ~70%
• Legal Status: Rx-only USA
• Pregnancy Category: C (USA), D (Au)
• Gene Information: human ... ABCB1(5243), CYP2C9(1559), CYP2D6(1565)rat ... Cyp2d1(266684), Cyp2d2(25053), Cyp2d3(24303), Cyp2d4v1(171522)

Product Information

• Purity: ≥98.0% (dried material, NT); 90%
• Grade: certified reference material; TraceCERT®
• Suitability: suitable for fluorescence
• Impurities: ≤5% dihydroquinine (HPLC)
• Shelf Life: (limited shelf life, expiry date on the label)
• Loss on Drying: ≤1% loss on drying, 110 °C
• Empirical Formula (Hill Notation): C20H24N2O2

DETAILS

Sigma Aldrich - Q1878

Biochem/physiol Actions
Potassium channel blocker

Sigma Aldrich - 22620

Biochem/physiol Actions
Potassium channel blocker
Other Notes
Chiral catalyst, used e.g. in highly enantioselective [2+2] cycloadditions1,2; In additions of diethylzinc to aldehydes.3

Sigma Aldrich - 145904

Biochem/physiol Actions
Potassium channel blocker
Other Notes
remainder hydroquinine
Packaging
10, 50 g in poly bottle
Application
Resolving agent for carboxylic acids.1 Catalyzes the kinetic resolution of furanones.2

Sigma Aldrich - 69311

Biochem/physiol Actions
钾通道阻断剂。
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC