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

• ChemBase ID: 784
• Molecular Formular: C20H24N2O2
• Molecular Mass: 324.41676
• Monoisotopic Mass: 324.18377802
• SMILES: O[C@H]([C@@H]1N2C[C@@H]([C@H](C1)CC2)C=C)c1c2c(ncc1)ccc(OC)c2
• 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-LHHVKLHASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
• IUPAC Traditional name: quinidine; quinidine sulphate
• Brand Name: Apo-Quinidine; Biquin Durules; Cardioquin; Chinidin; Cin-Quin; Coccinine; Conchinin; Conchinine; Conquinine; Duraquin; Kinidin; Novoquinidin; Pitayin; Pitayine; Quin-Release; Quinact; Quinaglute; Quinaglute Dura-Tabs; Quinalan; Quinate; Quinatime; Quindine; Quinicardine; Quinidex; Quinidex Extentabs; Quinora
• Synonyms: (1S)-(6-Methoxyquinolin-4-yl)((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol; (2-ethenyl- 4-azabicyclo [2.2.2] oct- 5-yl)- (6-methoxyquinolin- 4-yl)- methanol,; Quinidine; Quinidine Sulfate; Quinidine Gluconate; Quinidine; QUINIDINE GLUCONATE; 奎尼丁

Database IDs

• CAS Number: 56-54-2
• EC Number: 200-279-0
• MDL Number: MFCD00135581
• Beilstein Number: 91866
• PubChem SID: 24899331; 160964247; 24853537; 46505356
• PubChem CID: 441074
• CHEBI ID: 28593
• ATC CODE: C01BA01
• CHEMBL: 97
• Chemspider ID: 389880
• DrugBank ID: DB00908
• IUPHAR ligand ID: 2342
• Unique Ingredient Identifier: ITX08688JL
• Wikipedia Title: Quinidine

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 2.82
• LOG S: -2.99
• Solubility (Water): 3.34e-01 g/l

PROPERTIES

Physical Property

• Solubility: 140 mg/L
• Melting Point: 168-172 °C(lit.)
• Optical Rotation: [α]20/D +265±5°, c = 0.8% in ethanol (dry matter)
• Hydrophobicity(logP): 2.6

Safety Information

• Storage Warning: IRRITANT
• RTECS: VA4725000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• Safety Statements: 36
• TSCA Listed: false
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 70-80%
• Excretion: Renal
• Half Life: 6-8h
• Metabolism: 50-90% Hepatic
• Gene Information: human ... ABCB1(5243), CYP2D6(1565), CYP3A4(1576), KCNH1(3756)mouse ... Abcb1a(18671), Abcb1b(18669)rat ... Cyp2d1(266684), Cyp2d2(25053), Cyp2d3(24303), Cyp2d4v1(171522)

Product Information

• Purity: ≥98.0% (dried material, NT); 95+%; 97%
• Grade: anhydrous
• Impurities: ~10% hydroquinidine (HPLC); ≤2% water; ≤20% Dihydroquinidine (according to USP specifications., actual content given on label)
• Quality: crystallized
• Empirical Formula (Hill Notation): C20H24N2O2

DETAILS

MP Biomedicals - 05206337

MP Biomedicals Rare Chemical collection

DrugBank - DB00908

• Drug Groups: approved
• Description: An optical isomer of quinine, extracted from the bark of the Cinchona tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular action potential, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission. [PubChem]
• Indication: For the treatment of ventricular pre-excitation and cardiac dysrhythmias
• Pharmacology: Quinidine, a hydantoin anticonvulsant, is used alone or with phenobarbital or other anticonvulsants to manage tonic-clonic seizures, psychomotor seizures, neuropathic pain syndromes including diabetic neuropathy, digitalis-induced cardiac arrhythmias, and cardiac arrhythmias associated with QT-interval prolongation.
• Affected Organisms: Humans and other mammals
• Half Life: 6-8 hours
• Protein Binding: 80-88%
• Elimination: When the urine pH is less than 7, about 20% of administered quinidine appears unchanged in the urine, but this fraction drops to as little as 5% when the urine is more alkaline.
• Distribution: * 2 to 3 L/kg; * 0.5 L/kg [congestive heart failure]; * 3 to 5 L/kg [cirrhosis of the liver]
• Clearance: * 3 – 5 mL/min/kg [adults]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - Q3625

Biochem/physiol Actions
Class IA antiarrhythmic; potassium channel blocker.
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 22600

Biochem/physiol Actions
Class IA antiarrhythmic; potassium channel blocker.
Other Notes
Chiral catalyst, used e.g. in highly enantioselective [2+2] cycloadditions1,2,3
Packaging
10, 50 g in poly bottle