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Merck
CN

22600

Quinidine

crystallized, ≥98.0% (dried material, NT)

Synonym(s):

β-Quinidine, (+)-Quinidine, (9S)-6′-Methoxycinchonan-9-ol, Chinidin

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About This Item

Empirical Formula (Hill Notation):
C20H24N2O2
CAS Number:
56-54-2
Molecular Weight:
324.42
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
57647992
EC Number:
200-279-0
Beilstein/REAXYS Number:
91866
MDL number:
MFCD00135581

Key Documents

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Product Name

Quinidine, crystallized, ≥98.0% (dried material, NT)

InChI key

LOUPRKONTZGTKE-LHHVKLHASA-N

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

SMILES string

COc1ccc2nccc([C@H](O)C3CC4CCN3C[C@@H]4C=C)c2c1

assay

≥98.0% (dried material, NT)

form

solid

optical activity

[α]20/D +265±5°, c = 0.8% in ethanol (dry matter)

quality

crystallized

impurities

≤2% water
~10% hydroquinidine (HPLC)

mp

168-172 °C (lit.)

functional group

hydroxyl

Quality Level

100

Gene Information

human ... ABCB1(5243), CYP2D6(1565), CYP3A4(1576), KCNH1(3756), SCN10A(6336), SCN11A(11280), SCN1A(6323), SCN2A(6326), SCN3A(6328), SCN4A(6329), SCN5A(6331), SCN7A(6332), SCN8A(6334), SCN9A(6335)
mouse ... Abcb1a(18671), Abcb1b(18669)
rat ... Cyp2d1(266684), Cyp2d2(25053), Cyp2d3(24303), Cyp2d4v1(171522)

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Application

Quinidine may be used in the preparation of O-trimethylsilylquinidine by reacting trimethylsilyl chloride.

Biochem/physiol Actions

Class IA antiarrhythmic; potassium channel blocker.

General description

Quinidine is an isomer of quinine.

Other Notes

Chiral catalyst, used e.g. in highly enantioselective [2+2] cycloadditions

wgk

WGK 1

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301,H317

Hazard Classifications

Acute Tox. 3 Oral - Skin Sens. 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH8905
BCBZ3910
BCBP9110V
BCBB6721
BCBB4073

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P.E. Ketelaar et al.
Tetrahedron Letters, 26, 4665-4665 (1985)
The Journal of Organic Chemistry, 50, 1977-1977 (1985)
Organocatalytic enantioselective synthesis of bicyclic ?-lactones from aldehyde acids via nucleophile-catalyzed aldol-lactonization (NCAL).
Nguygen et al.
Organic Syntheses, 88, 121-137 (2011)
Bernard Belhassen et al.
Circulation, 110(13), 1731-1737 (2004-09-24)
Automatic implantable cardioverter-defibrillator therapy is considered the only effective treatment for high-risk patients with Brugada syndrome. Quinidine depresses I(to) current, which may play an important role in the arrhythmogenesis of this disease. The effects of quinidine bisulfate (mean dose, 1483+/-240
H. Wynberg et al.
Journal of the American Chemical Society, 104, 166-166 (1982)
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Protocols

LC/MS/MS Analysis of Interacting Cardiac Drugs Digoxin, Quinidine, Amiodarone and Verapamil on Titan™ C18

LC/MS/MS Analysis of Interacting Cardiac Drugs Digoxin, Quinidine, Amiodarone and Verapamil on Titan™ C18

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