EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

quinidine
cinchonan-9-ol, 6'-methoxy-, (3a,9S)-

Supplier Sponsors

Name:(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
CAS Number: 56-54-2Picture of molecule3D/inchi
Other(deleted CASRN):11010-73-4
ECHA EINECS - REACH Pre-Reg:200-279-0
FDA UNII: ITX08688JL
Nikkaji Web:J4.570E
Beilstein Number:91866
MDL:MFCD00135581
XlogP3:2.90 (est)
Molecular Weight:324.42368000
Formula:C20 H24 N2 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:white crystals or powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 174.00 °C. @ 760.00 mm Hg
Boiling Point: 495.88 °C. @ 760.00 mm Hg (est)
Flash Point: 489.00 °F. TCC ( 253.70 °C. ) (est)
logP (o/w): 3.440
Soluble in:
 water, 140 mg/L @ 25 °C (exp)
 water, 103.6 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Quinidine 98%
BOC Sciences
For experimental / research use only.
Conquinine 98%
Odor: characteristic
Use: Conquinine is a Cytochrome P450 2D6 inhibitor. It is a dextrorotatory stereoisomer of quinine extracted from the bark of the Cinchona tree and similar plant species. It is an alkaloid with class 1A antiarrhythmic and antimalarial effects.
ExtraSynthese
For experimental / research use only.
Quinidine (HPLC) ≥90%
Santa Cruz Biotechnology
For experimental / research use only.
Quinidine ≥97%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Quinidine crystallized, ≥98.0% (dried material, NT)
TCI AMERICA
For experimental / research use only.
Quinidine >98.0%(T)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-cat LD50 30 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 226, Pg. 286, 1977.

unreported-mammal (species unspecified) LD50 67 mg/kg
Farmakologiya i Toksikologiya Vol. 48(5), Pg. 43, 1985.

intramuscular-mouse LD50 200 mg/kg
"Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 232, 1973.

intraperitoneal-mouse LD50 135 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 410, 1962.

intravenous-mouse LD50 53600 ug/kg
Journal of Medicinal Chemistry. Vol. 27, Pg. 1142, 1984.

oral-mouse LD50 535 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 291, 1952.

intravenous-rat LD50 23 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 128, Pg. 22, 1960.

oral-rat LD50 263 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 27, Pg. 589, 1977.

unreported-rat LD50 60 mg/kg
Farmakologiya i Toksikologiya Vol. 54(3), Pg. 32, 1991.

Dermal Toxicity:
subcutaneous-mouse LDLo 400 mg/kg
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for quinidine usage levels up to:
 not for fragrance use.
 
Recommendation for quinidine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):56-54-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5953
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Chemidplus:0000056542
EPA/NOAA CAMEO:hazardous materials
RTECS:VA4725000 for cas# 56-54-2
 
References:
 (S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5953
Pubchem (sid):134972764
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
Metabolomics Database:Search
KEGG (GenomeNet):C06527
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2933.49.7000
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•available as capsules: 200and 300 mg; injection: 200 mgml; tablets: 100, 200 and 300 mg; sustained-release tablets: 300 mg quinidine sulfate, as injection: 800 mg10 ml; extended-release tablets: 324 and 330 mg quinidine gluconate and as tablets: 275 mg quinidine polygalacturonate •quinaglute dura-tabs contain 5 gr quinidine gluconate per tablet •quinidex exten-tabs contain 300 mg quinidine sulfate per tablet •duraquin contains 330 mg quindine gluconate per tablet •cardioquin tablets contain 275 mg of quinidine polygalacturonate per tablet •quinora tablets contain 200 or 300 mg of quinidine sulfate per tablet •oral tablets, extended release, 324 mg (equivalent to quinidine 202 mg) quinaglute dura-tabs, berlex; parenteral injection, 80 mg (equivalent to quinidine 50 mg) per ml, quinidine gluconate injection (with edetate disodium and phenol), lilly. quinidine gluconate •oral tablets contain 275 mg (equivalent to quinidine sulfate 200 mg), cardioquin (with povidone scored), purdue frederick. quinidine polygalacturonate •oral tablets, 200 mg, 300 mg; tablets, extended-release, 300 mg, quinidex extentabs, robins. quinidine sulfate •duraquin, quinaglute quinidine gluconate •cardioquin, galactoquin, naticardina quinidine polygalacturonate
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 biquin durules
 cardioquin
 chinidin
 cinchonan-9-ol, 6'-methoxy-, (3a,9S)-
 cinchonan-9-ol, 6'-methoxy-, (9S)-
 coccinine
 conchinin
(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]oct-2-yl](6-methoxyquinolin-4-yl)methanol
(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
(S)-(6-methoxy-4-quinolinyl)[(2R,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methanol
(9S)-6-methoxy-a-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol
(3'a, 9S)-6'-methoxycinchonan-9-ol
(3a,9S)-6'-methoxycinchonan-9-ol
(8R,9S)-6'-methoxycinchonan-9-ol
(9S)-6'-methoxycinchonan-9-ol
(1S)-(6-methoxyquinolin-4-yl)((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol
 novoquinidin
 pitayin
 quin-release
 quinact
 quinaglute dura-tabs
 quinalan
 quinatime
 quindine
 quinidex
 quinidex extentabs
(+)-quinidine
(8R,9S)-quinidine
apo-quinidine
 quiniduran
 

Articles:

PubMed:Dextromethorphan/Quinidine for the treatment of pseudobulbar affect.
PubMed:Pseudobulbar affect: prevalence and management.
PubMed:In vitro predictability of drug-drug interaction likelihood of P-glycoprotein-mediated efflux of dabigatran etexilate based on [I]2/IC50 threshold.
PubMed:Validation of a population-based method to assess drug-induced alterations in the QT interval: a self-controlled crossover study.
PubMed:Application of receiver operating characteristic analysis to refine the prediction of potential digoxin drug interactions.
PubMed:In vitro to in vivo extrapolation and physiologically based modeling of cytochrome P450 mediated metabolism in beagle dog gut wall and liver.
PubMed:Capillary electrophoresis methods for the analysis of antimalarials. Part I. Chiral separation methods.
PubMed:Randomized open-label drug-drug interaction trial of dextromethorphan/quinidine and paroxetine in healthy volunteers.
PubMed:Atrial fibrillation (acute onset).
PubMed:Human liver enzymes responsible for metabolic elimination of tyramine; a vasopressor agent from daily food.
PubMed:Inhibition of cytochrome P450 2A participating in coumarin 7-hydroxylation in pig liver microsomes.
PubMed:In vitro biotransformation and investigation of metabolic enzymes possibly responsible for the metabolism of bisdesoxyolaquindox in the liver fractions of rats, chicken, and pigs.
PubMed:Coffee, broccoli and spices are strong inducers of electrophile response element-dependent transcription in vitro and in vivo - studies in electrophile response element transgenic mice.
PubMed:Intravenous artesunate for the treatment of severe malaria.
PubMed:Enantiomer separation and indirect chromatographic absolute configuration prediction of chiral pirinixic acid derivatives: Limitations of polysaccharide-type chiral stationary phases in comparison to chiral anion-exchangers.
PubMed:Chirally functionalized anion-exchange type silica monolith for enantiomer separation of 2-aryloxypropionic acid herbicides by non-aqueous capillary electrochromatography.
PubMed:Practice parameter update: the care of the patient with amyotrophic lateral sclerosis: multidisciplinary care, symptom management, and cognitive/behavioral impairment (an evidence-based review): report of the Quality Standards Subcommittee of the American Academy of Neurology.
PubMed:Involuntary emotional expression disorder in Alzheimer's disease - psychopharmacotherapy aspects.
PubMed:Multiple efflux pumps are involved in the transepithelial transport of colchicine: combined effect of p-glycoprotein and multidrug resistance-associated protein 2 leads to decreased intestinal absorption throughout the entire small intestine.
PubMed:Parallel functional activity profiling reveals valvulopathogens are potent 5-hydroxytryptamine(2B) receptor agonists: implications for drug safety assessment.
PubMed:The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport.
PubMed:Assessing the efficiency of mixed effects modelling in quantifying metabolism based drug-drug interactions: using in vitro data as an aid to assess study power.
PubMed:Validation of cytochrome P450 time-dependent inhibition assays: a two-time point IC50 shift approach facilitates kinact assay design.
PubMed:Dextromethorphan/quinidine sulfate for pseudobulbar affect.
PubMed:Separation of Cinchona alkaloids on a novel strong cation-exchange-type chiral stationary phase-comparison with commercially available strong cation exchanger and reversed-phase packing materials.
PubMed:Grapefruit juice and its constituents augment colchicine intestinal absorption: potential hazardous interaction and the role of p-glycoprotein.
PubMed:Grapefruit juice-drug interaction studies as a method to assess the extent of intestinal availability: utility and limitations.
PubMed:Synergistic effects on enantioselectivity of zwitterionic chiral stationary phases for separations of chiral acids, bases, and amino acids by HPLC.
PubMed:Validation and application of Caco-2 assays for the in vitro evaluation of development candidate drugs as substrates or inhibitors of P-glycoprotein to support regulatory submissions.
PubMed:Interaction of coenzyme Q10 with the intestinal drug transporter P-glycoprotein.
PubMed:The causes and treatment of pseudobulbar affect in ischemic stroke.
PubMed:Impact of the changes in P-glycoprotein activity on domperidone pharmacokinetics in rat plasma.
PubMed:Atrial fibrillation (acute onset).
PubMed:The additive effects of the active component of grapefruit juice (naringenin) and antiarrhythmic drugs on HERG inhibition.
PubMed:An improved synthesis of 10,11-didehydro Cinchona alkaloids.
PubMed:Involuntary emotional expression disorder: treating the untreated.
PubMed:A real reason for patients with pseudobulbar affect to smile.
PubMed:Stereoselective separations of chiral phosphinic acid pseudodipeptides by CEC using silica monoliths modified with an anion-exchange-type chiral selector.
PubMed:Liquid chromatographic analysis of cinchona alkaloids in beverages.
PubMed:The procerebrum is necessary for odor-aversion learning in the terrestrial slug Limax valentianus.
PubMed:The complexity of intestinal absorption and exsorption of digoxin in rats.
PubMed:Deuterium isotope effects observed during competitive binding chiral recognition electrospray ionization--mass spectrometry of cinchona alkaloid-based systems.
PubMed:Review of pseudobulbar affect including a novel and potential therapy.
PubMed:Effects of dietary or injected organic cations on larval Drosophila melanogaster: mortality and elimination of tetraethylammonium from the hemolymph.
PubMed:Impairment of olfactory discrimination by blockade of nitric oxide activity in the terrestrial slug Limax valentianus.
PubMed:Interactions between grapefruit juice and cardiovascular drugs.
PubMed:A review of the safety and efficacy of droperidol for the rapid sedation of severely agitated and violent patients.
PubMed:Up-regulation of vascular and renal mitogen-activated protein kinases in hypertensive rats is normalized by inhibitors of the Na+/Mg2+ exchanger.
PubMed:Delayed-onset amnesia caused by protein synthesis inhibition in odor-taste associative memory of the terrestrial slug Limax valentianus.
PubMed:Clinical pharmacokinetics of reboxetine, a selective norepinephrine reuptake inhibitor for the treatment of patients with depression.
PubMed:Interaction of chloroquine and its analogues with heme: An isothermal titration calorimetric study.
PubMed:Mechanism of cardiotoxicity of halofantrine.
PubMed:Behavioral modulation induced by food odor aversive conditioning and its influence on the olfactory responses of an oscillatory brain network in the slug Limax marginatus.
PubMed:Evaluation of a Cmin and a normalized Cmin method for the confirmation of steady-state in bioequivalence studies.
PubMed:Female gender as a risk factor for drug-induced cardiac arrhythmias: evaluation of clinical and experimental evidence.
PubMed:Selective biotransformation of the human immunodeficiency virus protease inhibitor saquinavir by human small-intestinal cytochrome P4503A4: potential contribution to high first-pass metabolism.
PubMed:[Cardiovascular risk for the traveler].
PubMed:Effect of quinidine on kidney biochemistry and function in male Sprague-Dawley rats.
PubMed:Metabolism of taxol by human and rat liver in vitro: a screen for drug interactions and interspecies differences.
PubMed:Comparison of single and multiple dose pharmacokinetics using clinical bioequivalence data and Monte Carlo simulations.
PubMed:Effect of drug formulation and feeding on the pharmacokinetics of orally administered quinidine in the horse.
PubMed:Mechanism of the cardiotoxic actions of terfenadine.
PubMed:Very low calorie diets and pre-fasting prolonged QT interval. A hidden potential danger.
PubMed:Antiparasitic agents.
PubMed:Behavioral analysis of internal memory states using cooling-induced retrograde amnesia in Limax flavus.
PubMed:Antiarrhythmic properties of triamterene derivatives in the coronary artery ligated rat model.
PubMed:Treatment of cardiovascular disease in cattle.
PubMed:Bioconversion of quininone to quinidine by resting cells of Hansenula anomala var. schneggii.
PubMed:In vitro testing of triamterene derivatives for antiarrhythmic activity.
PubMed:Effect of dietary fat content on the bioavailability of a sustained release quinidine gluconate tablet.
PubMed:Antiarrhythmic activity of the local anaesthetic fomocaine and some of its analogues.
PubMed:Alkaloid Production by Transformed Root Cultures of Cinchona ledgeriana.
PubMed:Propafenone: a new antiarrhythmic agent.
PubMed:Application of 1H-nuclear magnetic resonance spectroscopic method for quinidine to simultaneous determination of quinidine and dihydroquinidine in quinidine sulfate tablets.
PubMed:Discriminative conditioning alters food preferences in the leech, Haemopis marmorata.
PubMed:Digitalis. An update of clinical pharmacokinetics, therapeutic monitoring techniques and treatment recommendations.
PubMed:Clinical pharmacokinetics of ibopamine on different diseases and conditions.
PubMed:Chronic ventricular arrhythmias: which drug for which patient?
PubMed:New antiarrhythmic drugs: tocainide, mexiletine, flecainide, encainide, and amiodarone.
PubMed:Prediction of steady-state bioequivalence relationships using single dose data I-linear kinetics.
PubMed:Comparison of high pressure liquid chromatography and fluorescence polarization immunoassay to assess quinidine pharmacokinetics.
PubMed:Toxicity of quinoline alkaloids to cultured Cinchona ledgeriana cells.
PubMed:Use of nitrite and hypochlorite treatments in determination of the contributions of IQ-type and non-IQ-type heterocyclic amines to the mutagenicities in crude pyrolyzed materials.
PubMed:Study of IV quinidine gluconate for severe malaria.
PubMed:Liquid chromatographic determination of quinine, hydroquinine, saccharin, and sodium benzoate in quinine beverages.
PubMed:In vitro expression of in vivo learning by an isolated molluscan CNS.
PubMed:Urinary excretion kinetics of intact quinidine and 3-OH-quinidine after oral administration of a single oral dose of quinidine gluconate in the fasting and non-fasting state.
PubMed:Microbiological reduction of quininone to quinidine.
PubMed:One-trial associative learning by an isolated molluscan CNS: use of different chemoreceptors for training and testing.
PubMed:Effect of food and an antacid on quinidine bioavailability.
PubMed:Influence of food on the comparative bioavailability of a fast- and slow-release dosage form of quinidine gluconate.
PubMed:The second peak in the serum levels curve after oral administration of a slow-release quinidine dosage form: effect of food.
PubMed:Serious bioavailability problems with a generic prolonged-release quinidine gluconate product.
PubMed:One-trial associative learning modifies food odor preferences of a terrestrial mollusc.
PubMed:Effect of food on enteral absorption of quinidine.
PubMed:Absorption of quinidine from an enteric-coated preparation.
PubMed:Trialwise tracking method for measuring drug-affected sensory threshold changes in animals.
PubMed:The influence of tablet hardness and food intake on the absorption of drugs.
 
Notes:
an optical isomer of quinine, 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.
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