22600

Quinidine

crystallized, ≥98.0% (dried material, NT)

• 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
• UNSPSC Code: 12352103
• NACRES: NA.22
• PubChem Substance ID: 57647992
• EC Number: 200-279-0
• Beilstein/REAXYS Number: 91866
• MDL number: MFCD00135581

Properties

• Quality Segment: 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.)
• functional group: hydroxyl
• 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

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

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301,H317
• pcodes: P261 - P264 - P272 - P280 - P301 + P310 - P302 + P352
• 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
• wgk: WGK 1
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves