Basic information
- CAS
56-54-2- Standard SMILES
C=CC1CN2CCC1CC2[C@@H](O)c1ccnc2ccc(OC)cc12- InChIKey
LOUPRKONTZGTKE-LHFMAAMQSA-N- Molecular formula
- C20H24N2O2
- Average molar mass
- 324.4 g/mol
- Monoisotopic mass
- 324.18377801
Overview
See also: Quinidine (annotation moved to); Quinine Sulfate (annotation moved to); Epiquinidine (annotation moved to).
Names & identifiers
- Preferred name
- (6-Methoxy-quinolin-4-yl)-(5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol
- IUPAC
- (S)-(5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanol
- English name
- Quinidine
- Molecular formula
- C20H24N2O2
- Molecular weight
- 324.42
Names & synonyms
EpichinidinQuindine.beta.-QuinineCHEMBL170Pitayin(8R,9S)-6'-Methoxycinchonan-9-ol(6-Methoxy-quinolin-4-yl)-(5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanolNCGC00159499-02(+)-QuindineQuinora (Salt/Mix)Quinidex (Salt/Mix)Quinitex (Salt/Mix)
Show more names
QUNIDINEChinidin(S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanolCin-quinQuinidexQuinagluteCONCHININE(+)-Quinidine6-METHOXY-A-(5-VINYL-2-QUINUCLIDINYL)-4-QUINOLINE-METHANOL
Systodin (Salt/Mix)CHEMBL97Quinicardine (Salt/Mix)MLS0060119562-Quinuclidinemethanol, .alpha.-(6-methoxy-4-quinolyl)-5-vinyl-SCHEMBL1695442LOUPRKONTZGTKE-LHFMAAMQSA-NBDBM50017681
Database identifiers
- CAS
56-54-2
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 45.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 457
Physicochemical properties
- Melting point
- 168 · 168-172 °C(lit.)
- alpha
- 256 · 256 º (c=1, EtOH)
- Boiling point
- 462.75 °C · 462.75°C (rough estimate)
- Density
- 1.1294 · 1.1294 (rough estimate)
- refractive index
- 1.57 · 1.5700 (estimate)
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- solubility
- 2 O; · insoluble in H2O; ≥10.32 mg/mL in EtOH with ultrasonic; ≥11.95 mg/mL in DMSO
- form
- Powder
- pka
- 5.4 · 5.4, 10.0(at 20℃)
- color
- White to off-white
- optical activity
- 20 · [α]20/D +265±5°, c = 0.8% in ethanol (dry matter)
- Water Solubility
- 0.05 g/100 · 0.05 g/100 mL (20 ºC)
- Sensitive
- Light Sensitive
- Merck
- 14 · 14,8060
- BRN
- 91866 · 91866
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 8
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- VA4725000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29392000
- Toxicity
- LD50 in rats (mg/kg): 30 i.v., 263 orally (Dietmann)
- risk_code
- 22-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn
- safety_code
- 36-22
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301-H317
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 OralSkin Sens. 1
- Precautionary statements
- P261-P264-P270-P280-P301+P310-P302+P352
- Hazardous Substances Data
- 56-54-2(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionQuinidine is a stereoisomer of the antimalarial agent quinine and a class Ia antiarrhythmic agent. Quinidine blocks the voltage-gated sodium (Nav) channel Nav1.5 in a use-dependent manner. It decreases the amplitude and duration of action potentials in isolated canine ventricular myocytes. It inhibits KKr, peak INa, and late INa (IC50s = 4.5, 11, and 12 μM, respectively) and can induce torsade de pointes in isolated rabbit hearts when used at a concentration of 1 μM. Quinidine induces QT prolongation in dogs. It also binds to M2 muscarinic acetylcholine receptors (Ki = 7.5 μM for human recombinant receptors expressed in HM2-B10 cells). Formulations containing quinidine have been used in the treatment of atrial fibrillation and ventricular arrhythmias.
DescriptionQuinidine is a commonly used class I antiarrhythmic drug. It is a stereoisomer of quinine, originally derived from the bark of the cinchona tree. It exerts its antiarrhythmic effects on the heart by interacting with the electrophysiology mechanisms that cause arrhythmias to modify the abnormalities in impulse initiation and conduction. Quinidine depresses normal automaticity in cardiac fibers that may act as ectopic pacemakers causing arrhythmias. Quinidine also blocks the slowly inactivating, tetrodotoxin-sensitive Na current, the slow inward calcium current (ICa), the rapid (IKr) and slow (IKs) components of the delayed potassium rectifier current, the inward potassium rectifier current (IKI), the ATP-sensitive potassium channel (IKATP) and Ito.
HistoryIn 1820, the French chemists Pierre Pelletier and Joseph Caventou extracted some alkaloids from the cinchona bark, including quinine and quinidine. Subsequently, quinine was demonstrated to play a very important role in the treatment of malaria after a number of scientific researches. Quinidine is the dextroisomer of quinine and has the similar pharmacological properties as quinine, but quinidine’s effects are five to ten times stronger on the heart than quinine.
UsesQuinidine 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.
UsesA dextrorotatory stereoisomer of Quinine. Antiarrhythmic (class IA). Antimalarial
Usesantiarrhythmic, antimalarial
Crystals or white powder.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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