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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O2
Molecular Weight 324.4168
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUININE

SMILES

COC1=CC=C2N=CC=C([C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)C2=C1

InChI

InChIKey=LOUPRKONTZGTKE-WZBLMQSHSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.fda.gov/downloads/ForHealthProfessionals/LearningActivities/UCM317816.pdf

Quinine soluble salts possess the extremely bitter taste, that may have a perplexing problem especially to children. That is why the most common combinations which are administered in this way are the sulphate, salicylate, tannate and certain esters. Quinine tannate, an insoluble quinine salt has been known in medicine for a very long time. However, many experiments have revealed that quinine tannate was practically inert as a medicinal substance.

Approval Year

1921
1468
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
QUALAQUIN

Approved Use

is a cinchona alkaloid indicated for treatment of uncomplicated Plasmodium falciparum malaria

Launch Date

2005
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.2 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021799s029lbl.pdf
8.7 mg/kg single, oral
dose: 8.7 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUININE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
28 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021799s029lbl.pdf
8.7 mg/kg single, oral
dose: 8.7 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUININE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.5 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021799s029lbl.pdf
8.7 mg/kg single, oral
dose: 8.7 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUININE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
8%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021799s029lbl.pdf
8.7 mg/kg single, oral
dose: 8.7 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUININE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5 g single, oral
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/2566088
unhealthy, 17 years
Health Status: unhealthy
Age Group: 17 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2566088
Other AEs: Respiratory distress...
Other AEs:
Respiratory distress (grade 5, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2566088
1.8 g single, oral
Overdose
Dose: 1.8 g
Route: oral
Route: single
Dose: 1.8 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/28778932
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28778932
Other AEs: Hearing loss...
Other AEs:
Hearing loss (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28778932
16250 mg single, oral
Overdose
Dose: 16250 mg
Route: oral
Route: single
Dose: 16250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8340583
unhealthy, 49 years
Health Status: unhealthy
Age Group: 49 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8340583
Other AEs: Cardiotoxicity...
Other AEs:
Cardiotoxicity (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8340583
9.75 g single, oral
Dose: 9.75 g
Route: oral
Route: single
Dose: 9.75 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/14640479
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/14640479
Other AEs: Tachycardia...
Other AEs:
Tachycardia (grade 5)
Sources:
https://pubmed.ncbi.nlm.nih.gov/14640479
AEs

AEs

AESignificanceDosePopulation
Respiratory distress grade 5, 1 patient
5 g single, oral
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/2566088
unhealthy, 17 years
Health Status: unhealthy
Age Group: 17 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2566088
Hearing loss 1 patient
1.8 g single, oral
Overdose
Dose: 1.8 g
Route: oral
Route: single
Dose: 1.8 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/28778932
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28778932
Cardiotoxicity 1 patient
16250 mg single, oral
Overdose
Dose: 16250 mg
Route: oral
Route: single
Dose: 16250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8340583
unhealthy, 49 years
Health Status: unhealthy
Age Group: 49 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8340583
Tachycardia grade 5
9.75 g single, oral
Dose: 9.75 g
Route: oral
Route: single
Dose: 9.75 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/14640479
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/14640479
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:15854
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15854
eMolecules
29549573
https://www.emolecules.com/cgi-bin/more?vid=29549573
eMolecules
30151887
https://www.emolecules.com/cgi-bin/more?vid=30151887
eMolecules
6843708
https://www.emolecules.com/cgi-bin/more?vid=6843708
MolPort
MolPort-000-146-082
https://www.molport.com/shop/molecule-link/MolPort-000-146-082
ZINC
ZINC000003831404
http://zinc15.docking.org/substances/ZINC000003831404
PubMed

PubMed

TitleDatePubMed
Role of parabrachial nucleus in submandibular salivary secretion induced by bitter taste stimulation in rats.
2001 Apr 12
Resurgence of blackwater fever in long-term European expatriates in Africa: report of 21 cases and review.
2001 Apr 15
Large-conductance calcium-activated potassium channels in neonatal rat intracardiac ganglion neurons.
2001 Feb
Delayed quinine toxicity mimicking open angle glaucoma.
2001 Feb
Computer-simulation studies on roles of potassium currents in neurotransmission of the auditory nerve.
2001 Feb
Activation of ion-conducting pathways in the inner mitochondrial membrane - an unrecognized activity of fatty acid?
2001 Feb 23
Characterization of an intense bitter-tasting 1H,4H-quinolizinium-7-olate by application of the taste dilution analysis, a novel bioassay for the screening and identification of taste-active compounds in foods.
2001 Jan
Effect of extracellular Ca2+ on the quinine-activated current of bullfrog taste receptor cells.
2001 Jan 15
Taste responses in sons of male alcoholics.
2001 Jan-Feb
Simultaneous determination of etoposide and its catechol metabolite in the plasma of pediatric patients by liquid chromatography/tandem mass spectrometry.
2001 Jul
The effect of laser assisted uvulopalatoplasty on the sense of smell and taste.
2001 Jun
Evaluation of the contribution to enantioselectivity of quinine and quinidine scaffolds in chemically and physically mixed chiral selectors.
2001 May 5
Resistance of Plasmodium falciparum to antimalarial drugs in a highly endemic area of southern Viet Nam: a study in vivo and in vitro.
2001 May-Jun
Optochin resistance in Streptococcus pneumoniae: mechanism, significance, and clinical implications.
2001 Sep 1
Patents

Patents

JP2002500227A
42
JP2003520193A
19
JP2010042013A
19
JP4679150B2
19
JPH04230322A
19
JPH04357199A
19
JPH067429A
19
JPH1171233A
19
JPS58216146A
19
JPS6112651A
19

Sample Use Guides

In Vivo Use Guide
in adults: 648 mg (two capsules) every 8 hours for 7 days
Route of Administration: Oral
In Vitro Use Guide
Quinine (0-100 uM) stimulates adipogenesis through ERK/S6 (extracellular-signal-regulated kinase/Ribosomal protein S6) signaling, which at least partly functions via taste receptor, type 2, member 106 (T2R106)
Name Type Language
QUININE
HSDB   INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
CHININUM PURUM
HPUS  
Preferred Name English
QUININE [MI]
Common Name English
QUININE [HSDB]
Common Name English
Quinine [WHO-DD]
Common Name English
QUININE [MART.]
Common Name English
REZQUIN
Common Name English
WR297608
Code English
CHININUM PURUM [HPUS]
Common Name English
(8S,9R)-6'-METHOXYCINCHONAN-9-OL
Common Name English
QUININE [VANDF]
Common Name English
QUALAQUIN
Common Name English
NSC-192949
Code English
Classification Tree Code System Code
NCI_THESAURUS C271
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
WHO-ATC P01BC01
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
CFR 21 CFR 862.3750
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
CFR 21 CFR 310.546
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
DSLD 2588 (Number of products:3)
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
CFR 21 CFR 172.575
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
CFR 21 CFR 310.547
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
NDF-RT N0000175482
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
WHO-VATC QM09AA72
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
WHO-ATC M09AA72
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
LIVERTOX NBK548596
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
Code System Code Type Description
CHEBI
15854
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
CHEBI
137041
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
CHEBI
52251
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
DAILYMED
A7V27PHC7A
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
DRUG CENTRAL
4523
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
FDA UNII
A7V27PHC7A
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
MESH
D011803
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
LACTMED
Quinine
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
IUPHAR
2510
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
ChEMBL
CHEMBL170
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
NSC
192949
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
WIKIPEDIA
QUININE
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
SMS_ID
100000078599
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-003-2
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
HSDB
2501
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
RXCUI
9071
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY RxNorm
CAS
130-95-0
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
NCI_THESAURUS
C794
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
DRUG BANK
DB00468
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
MERCK INDEX
m9447
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY Merck Index
EVMPD
SUB15084MIG
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
PUBCHEM
3034034
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID0044280
Created by admin on Mon Mar 31 17:50:50 GMT 2025 , Edited by admin on Mon Mar 31 17:50:50 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of QUININE
METABOLITE (PARENT)
Structure of 2'-OXOQUININE
METABOLITE (PARENT)
Structure of HYDROQUINIDINE
METABOLITE (PARENT)
Structure of CUPREINE
METABOLITE (PARENT)
Structure of QUININE GLUCURONIDE
METABOLITE LESS ACTIVE (PARENT)
Structure of 3-HYDROXYQUININE
SALT/SOLVATE (PARENT)
Structure of QUININE FORMATE
SALT/SOLVATE (PARENT)
Structure of QUININE HYDROCHLORIDE
SALT/SOLVATE (PARENT)
Structure of Quinine arsenite
SALT/SOLVATE (PARENT)
Structure of QUININE HYPOPHOSPHITE
SALT/SOLVATE (PARENT)
Structure of Penicillin G quinine
SALT/SOLVATE (PARENT)
Structure of Quinine arsenate
SALT/SOLVATE (PARENT)
Structure of QUININE UREA HYDROCHLORIDE
SALT/SOLVATE (PARENT)
Structure of QUININE ASCORBATE
SALT/SOLVATE (PARENT)
Structure of Phenobarbital quinine
SALT/SOLVATE (PARENT)
Structure of QUININE SULFATE
SALT/SOLVATE (PARENT)
Structure of QUININE CITRATE
SALT/SOLVATE (PARENT)
Structure of QUININE GLUCONATE
SALT/SOLVATE (PARENT)
Structure of QUININE DIHYDROBROMIDE
SALT/SOLVATE (PARENT)
Structure of QUININE SALICYLATE
SALT/SOLVATE (PARENT)
Structure of QUININE DIHYDROCHLORIDE
SALT/SOLVATE (PARENT)
Structure of QUININE BISULFATE
SALT/SOLVATE (PARENT)
Structure of QUININE PHOSPHATE
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