Category
Heterocyclic Organic Compound
Synonyms
(8R,9S)-6'-Methoxycinchonan-9-ol
IUPAC Name
(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;
Molecular Formula
C20H24N2O2
Canonical SMILES
COc1ccc2nccc([C@H](O)C3CC4CCN3C[C@@H]4C=C)c2c1
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
InChI Key
LOUPRKONTZGTKE-LHHVKLHASA-N
Solubility
less than 0.1 mg/mL at 64° F (NTP, 1992);8.15e-04 M;1 g /quinidine/ dissolves in about 36 ml alcohol, 56 ml ether, 1.6 ml chloroform; very soluble in methanol; practically insoluble in petroleum ether.;Soluble in benzene;In water, 140 mg/l @ 25 deg C;3.34e-01 g/L;>48.7 [ug/mL];
Appearance
Powder or Crystals
Application
Quinidine occurs in cinchona bark to about0.25-0.3% and also in cuprea bark. It is present in quinine sulfate mother liquor. Itis formed by isomerization of quinine. Itis used in the prevention of certain cardiacarrhythmias.Primary indications for the use of quinidine include (1) abolition of premature complexes that have an atrial, A-V junctional, or ventricular origin; (2) restoration of normal sinus rhythm in atrial flutter and atrial fibrillation after controlling the ventricular rate with digitalis; (3) maintenance of normal sinus rhythm after electrical conversion of atrial arrhythmias; (4) prophylaxis against arrhythmias associated with electrical countershock; (5) termination of ventricular tachycardia; and (6) suppression of repetitive tachycardia associated with Wolff- Parkinson-White (WPW) syndrome. Although quinidine often is successful in producing normal sinus rhythm, its administration in the presence of a rapid atrial rate (flutter and possibly atrial fibrillation) can lead to a further and dangerous increase in the ventricular rate secondary to inhibition of basal vagal tone upon the A-V node. For this reason, digitalis should be used before quinidine when one is attempting to convert atrial flutter or atrial fibrillation to normal sinus rhythm.
Color/Form
CRYSTALS WITH 2.5 MOL WATER OF CRYSTALLIZATION; CRYSTALS FROM DILUTE ALCOHOL;
Covalently-Bonded Unit Count
1
Decomposition
When heated to decomposition it emits toxic fumes of oxides of nitrogen.;
Defined Atom Stereocenter Count
4
Hydrogen Bond Acceptor Count
4
Hydrogen Bond Donor Count
1
Isomeric SMILES
COC1=CC2=C(C=CN=C2C=C1)[C@@H]([C@H]3C[C@@H]4CCN3C[C@@H]4C=C)O
Monoisotopic Mass
324.183778013
Octanol Water Partition Coefficient
3.44 (LogP);log Kow = 2.88;2.6;
Other Experimental
Prisms from dilute alcohol; loses one-half water in air; MP: about 168 deg C /Hemipentahydrate/;Lustrous needles; decomposes at 259 deg C (drug); specific optical rotation at 20 deg C/D + 200 deg ; sol in 60 parts water, freely soluble in hot water, in alcohol, chloroform, slightly in ether; neutral reaction. /Quinidine hydrochloride monohydrate/;Rods; soluble in 8 parts water with blue fluorescence /Acid sulfate tetrahydrate/;IR: 9516 (Sadtler Research Laboratories Prism Collection) /Quinidine hydrate/;MASS: 1940 (Atlas of Mass Spectral Data, John Wiley & Sons, New York) /Quinidine hydrate/;Crystals from water; decomposes at 115 deg C; specific optical rotation at 15 deg C/D + 223 deg (0.4 molar solution). /Quinidine dihydrobromide trihydrate/;Crystals from water; mp: 248 deg C (dry); readily soluble in hot water, alcohol. /Quinidine methiodide monohydrate/;Crystals; MP: 175-176.5 deg C; sol in 9 parts water, 60 parts alcohol /Gluconate/;
Physical Description
Crystals or white powder. (NTP, 1992);Solid;
Stability
Quinidine gluconate, quinidine polygalacturonate, and quinidine sulfate darken on exposure to light and should be stored in well-closed, light resistant containers. Solutions of quinidine salts slowly acquire a brownish tint on exposure to light. Only colorless, clear solutions of quinidine gluconate injection should be used. Quinidine gluconate injection should be stored at 15-30 deg C. When diluted to a concentration of 16 mg/ml with 5% dextrose injection, quinidine gluconate injection is stable for 24 hours at room temperature and up to 48 hours when refrigerated. /Quinidine salts/;
Topological Polar Surface Area
45.6
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