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22600

Sigma-Aldrich

Quinidine

crystallized, ≥98.0% (dried material, NT)

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Synonym(s):
β-Quinidine, (+)-Quinidine, (9S)-6′-Methoxycinchonan-9-ol, Chinidin
Empirical Formula (Hill Notation):
C20H24N2O2
CAS Number:
56-54-2
Molecular Weight:
324.42
Beilstein:
91866
EC Number:
200-279-0
MDL number:
MFCD00135581
UNSPSC Code:
12352103
PubChem Substance ID:
57647992
NACRES:
NA.22

Quality Level

100

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.)

SMILES string

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

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

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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General description

Quinidine is an isomer of quinine.

Application

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

Biochem/physiol Actions

Class IA antiarrhythmic; potassium channel blocker.

Other Notes

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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H317

Hazard Classifications

Acute Tox. 3 Oral - Skin Sens. 1

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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The Journal of Organic Chemistry, 50, 1977-1977 (1985)
P.E. Ketelaar et al.
Tetrahedron Letters, 26, 4665-4665 (1985)
Sami Viskin et al.
Journal of the American College of Cardiology, 61(23), 2383-2387 (2013-04-16)
The aim of this study was to determine the availability of quinidine throughout the world. Quinidine is the only oral medication that is effective for preventing life-threatening ventricular arrhythmias due to Brugada syndrome and idiopathic ventricular fibrillation. However, because of
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
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