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Q3625 Sigma-Aldrich

Quinidine

anhydrous

  • CAS Number 56-54-2

  • Empirical Formula (Hill Notation) C20H24N2O2

  • Molecular Weight 324.42

  •  Beilstein/REAXYS Number 91866

  •  EC Number 200-279-0

  •  MDL number MFCD00135581

  •  PubChem Substance ID 24899331

  •  NACRES NA.77

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Asymmetric Synthesis, Bayer, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   200
grade   anhydrous
impurities   ≤20% Dihydroquinidine (according to USP specifications., actual content given on label)
mp   168-172 °C (lit.)
originator   Bayer
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)

Description

Application

Quinidine has been used:
• as an inhibitor of cytochrome P450 enzyme isoform CYP2D6
• as a potassium (K+) channel blocker in microglia
• to test its effect on electrophysiological behaviour of human induced pluripotent stem cells (hiPSC) cardiomyocytes

Packaging

5, 25 g in glass bottle

Biochem/physiol Actions

Quinidine, an isomer of quinine has potential side effects like proarrhythmia on usage. It prolongs cardiac potential and is sodium channel blocker. It is a potential antagonist for α1-adrenoceptors and contributes to hypotension. It inhibits cytochrome P450 2D6 and improves circulation and brain penetration of dementia drug, dextromethorphan. Quinidine-dextromethorphan combination may be useful in treating pseudobulbar affect (PBA).

Class IA antiarrhythmic; potassium channel blocker.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 1
RTECS 
VA4725000
Protocols & Articles

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Peer-Reviewed Papers
15

References

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