Quinidine (CHEM016859)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:45:45 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016859
Identification
Common NameQuinidine
ClassSmall Molecule
DescriptionAn optical isomer of , extracted from the bark of the Cinchona tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular action potential, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-QuinidineChEBI
(8R,9S)-QuinidineChEBI
(R)-(6-Methoxyquinolin-4-yl)((3S,4R,7S)-3-vinylquinuclidin-7-yl)methanolChEBI
(S)-(6-Methoxy-quinolin-4-yl)-((2R,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanolChEBI
(S)-(6-Methoxyquinolin-4-yl)((2R,5R)-5-vinylquinuclidin-2-yl)methanolChEBI
6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanolChEBI
alpha-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanolChEBI
beta-QuinineChEBI
ChinidinChEBI
ChinidinumChEBI
CIN-quinChEBI
ConchininChEBI
ConquinineChEBI
KinidinChEBI
PitayineChEBI
QuinidinaChEBI
6-Methoxy-a-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanolGenerator
6-Methoxy-α-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanolGenerator
a-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanolGenerator
Α-(6-methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanolGenerator
b-QuinineGenerator
Β-quinineGenerator
Quinidine sulfateHMDB
QuincardineHMDB
Sulfate, quinidineHMDB
Apo-quinidineHMDB
Apotex brand OF quinidine sulfateHMDB
Fawns and mcallan brand OF quinidine sulfateHMDB
Apo quinidineHMDB
QuinidexHMDB
QuinoraHMDB
Robins brand OF quinidine sulfateHMDB
AdaquinHMDB
Nelson brand OF quinidine sulfateHMDB
Chemical FormulaC20H24N2O2
Average Molecular Mass324.417 g/mol
Monoisotopic Mass324.184 g/mol
CAS Registry Number56-54-2
IUPAC Name(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
Traditional Namequinidine
SMILES[H][C@@]12CCN(C[C@@H]1C=C)[C@]([H])(C2)[C@@H](O)C1=C2C=C(OC)C=CC2=NC=C1
InChI IdentifierInChI=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 KeyLOUPRKONTZGTKE-LHHVKLHASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCinchona alkaloids
Sub ClassNot Available
Direct ParentCinchona alkaloids
Alternative Parents
Substituents
  • Cinchonan-skeleton
  • 4-quinolinemethanol
  • Quinoline
  • Anisole
  • Quinuclidine
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Aromatic alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP2.82ALOGPS
logP2.51ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)9.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.59 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.69 m³·mol⁻¹ChemAxon
Polarizability35.82 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-1901000000-90466d795da1be8cafaeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-7947000000-ee233460f7e7fbb00ca7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0bt9-0908000000-f7ff24907014d8850472Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-08fr-0907000000-f6d31042d549da6bcfd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0bt9-0709000000-2c0e665e2c3031c8e517Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0009133000-a893d9e0e441c597fac3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0009001000-0a0220fd8eeb9e62bc20Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-02ta-3900000000-46a157d2899290cbf4abSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0200-2952000000-2777ab3374ec2b052b2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0469000000-3679f13f09481b3563c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0459000000-60c4a39356a4afeef2d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0239000000-644b48bb63dd87dac231Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0910000000-b0045fccdbe90e598912Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0229000000-f88b510f13aab6a2bb44Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-02ta-3900000000-46a157d2899290cbf4abSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0200-2952000000-2777ab3374ec2b052b2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00ai-6930000000-44317fd6318c96581c84Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-fe19371b962ad0614431Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0109000000-887063f0b5addd8d47c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0109000000-e84ce15e838ff8ac33f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0229000000-b87ca7a53d952af7505eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0540-0920000000-12d8977ce43e168f8453Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-a5389d6321d12f20cbdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0409000000-1083606bbf596253ea0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-0900000000-ea616a9e6496b54b3272Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0019000000-0f42379f2989cf204f72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0729000000-5a0d8aa890e6c737bf45Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00908
HMDB IDHMDB0015044
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkQuinidine
Chemspider ID389880
ChEBI ID28593
PubChem Compound ID441074
Kegg Compound IDC06527
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12477351
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12699389
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14971904
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14973303
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15089813
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15225721
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15270556
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15328252
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16570918
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=17132069
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17228875
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17249648
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17870541
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=18324762
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=18395298
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=18788725
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23861085
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24130427
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=445303
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=8337232
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=9864343