U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O2.ClH.2H2O
Molecular Weight 396.908
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUININE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=MPQKYZPYCSTMEI-FLZPLBAKSA-N
InChI=1S/C20H24N2O2.ClH.2H2O/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;1H;2*1H2/t13-,14-,19-,20+;;;/m0.../s1

HIDE SMILES / InChI
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C20H24N2O2
Molecular Weight 324.4168
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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
HPLC of basic drugs on microparticulate strong cation-exchange materials - a review.
2001-09-15
Properties and regulation of organic cation transport in freshly isolated human proximal tubules.
2001-09-07
Antimalarial activity of azithromycin, artemisinin and dihydroartemisinin in fresh isolates of Plasmodium falciparum in Thailand.
2001-09-01
Septic shock due to babesiosis.
2001-09-01
Optochin resistance in Streptococcus pneumoniae: mechanism, significance, and clinical implications.
2001-09-01
Effects of the ion-channel blocker quinine on human sperm volume, kinematics and mucus penetration, and the involvement of potassium channels.
2001-09
Is multiple sclerosis caused by a silent infection with malarial parasites? A historico-epidemiological approach: part II.
2001-09
Volume-activated trimethylamine oxide efflux in red blood cells of spiny dogfish (Squalus acanthias).
2001-09
Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1.
2001-09
Polyvinyl chloride-based membranes for flow injection analysis of quinine in beverages.
2001-08-15
Resistance of Plasmodium falciparum to antimalarial drugs in a highly endemic area of southern Viet Nam: a study in vivo and in vitro.
2001-08-09
The applicability of rat and human liver slices to the study of mechanisms of hepatic drug uptake.
2001-08-08
Quinine-induced thrombocytopenia in a 64-year-old man who consumed tonic water to relieve nocturnal leg cramps.
2001-08
5-HT1A receptor-mediated activation of G-protein-gated inwardly rectifying K+ current in rat periaqueductal gray neurons.
2001-08
Ferrocene-chloroquine analogues as antimalarial agents: in vitro activity of ferrochloroquine against 103 Gabonese isolates of Plasmodium falciparum.
2001-08
Role of quinine-sensitive ion channels in volume regulation in boar and bull spermatozoa.
2001-08
A clinical and pharmacokinetic trial of six doses of artemether-lumefantrine for multidrug-resistant Plasmodium falciparum malaria in Thailand.
2001-07-21
Clinical trial of beta-arteether versus quinine for the treatment of cerebral malaria in children in Yaounde, Cameroon.
2001-07-21
[Photodermatosis induced by hydroxychloroquine: 4 cases].
2001-07-19
A comparison of the in vivo kinetics of Plasmodium falciparum ring-infected erythrocyte surface antigen-positive and -negative erythrocytes.
2001-07-15
Distribution of gustatory sensitivities in rat taste cells: whole-cell responses to apical chemical stimulation.
2001-07-01
Effectiveness of short-course quinine and single-dose sulfadoxine-pyrimethamine in the treatment of Plasmodium falciparum malaria in Mpumalanga Province, South Africa.
2001-07
Covariation in individuals' sensitivities to bitter compounds: evidence supporting multiple receptor/transduction mechanisms.
2001-07
Apparent drug failure following artesunate treatment of Plasmodium falciparum malaria in Freetown, Sierra Leone: four case reports.
2001-07
Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells.
2001-07
Simultaneous determination of etoposide and its catechol metabolite in the plasma of pediatric patients by liquid chromatography/tandem mass spectrometry.
2001-07
Sapid solutions and food intake in repeated dehydration and rehydration periods in rats.
2001-07
Dynamic and multimodal responses of gustatory cortical neurons in awake rats.
2001-06-15
Transfusion-transmitted babesiosis in Ontario: first reported case in Canada.
2001-06-12
Myosin II-dependent cylindrical protrusions induced by quinine in Dictyostelium: antagonizing effects of actin polymerization at the leading edge.
2001-06
Lateral parabrachial nucleus lesions in the rat: neophobia and conditioned taste aversion.
2001-06
The effect of laser assisted uvulopalatoplasty on the sense of smell and taste.
2001-06
Influence of quinine on catecholamine release evoked by cholinergic stimulation and membrane depolarization from the rat adrenal gland.
2001-06
Therapeutic efficacy of sulphadoxine/pyrimethamine and susceptibility in vitro of P. falciparum isolates to sulphadoxine-pyremethamine and other antimalarial drugs in Malawian children.
2001-06
A comparison of brain, core and skin temperature in children with complicated and uncomplicated malaria.
2001-06
Nocturnal leg cramps. Clinically mysterious and painful--but manageable.
2001-06
Chemistry. Synthetic lessons from quinine.
2001-05-24
Treatment alternatives for nocturnal leg cramps.
2001-05-21
Oral quinine pharmacokinetics and dietary salt intake.
2001-05
Changes in taste intensity perception following anterior temporal lobe removal in humans.
2001-05
Effect of compound sequence on bitterness enhancement.
2001-05
Interaction of gustatory and lingual somatosensory perceptions at the cortical level in the human: a functional magnetic resonance imaging study.
2001-05
Role of parabrachial nucleus in submandibular salivary secretion induced by bitter taste stimulation in rats.
2001-04-12
The first stereoselective total synthesis of quinine.
2001-04-11
Quinine-induced alterations of electrically evoked otoacoustic emissions and cochlear potentials in guinea pigs.
2001-04
Cell volume-induced changes in K+ transport across the rat colon.
2001-04
Patterns of Plasmodium falciparum drug resistance in nonimmune travellers to Africa.
2001-04
Two procedures establishing preference for oral cocaine and lidocaine solutions which do not use an associative history with a reinforcer.
2001-04
Effects of hydroxypyridinone iron chelators in combination with antimalarial drugs on the in vitro growth of Plasmodium falciparum.
2001-03
Drug-induced thrombotic microangiopathy: incidence, prevention and management.
2001
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)
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:50:48 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:48 GMT 2025
Record UNII
711S8Y0T33
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUININE HYDROCHLORIDE DIHYDRATE
MART.   MI   USP-RS   WHO-DD  
Preferred Name English
QUININE HYDROCHLORIDE
EP   FCC   MART.   WHO-IP  
Common Name English
QUININE HYDROCHLORIDE [FCC]
Common Name English
QUININI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
(8.ALPHA.,9R)-6'-METHOXYCINCHONAN-9-OL HYDROCHLORIDE DIHYDRATE
Common Name English
QUININE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
QUININE MONOHYDROCHLORIDE
Common Name English
QUININE HYDROCHLORIDE DIHYDRATE [USP-RS]
Common Name English
CHININUM MURIATICUM
HPUS  
Common Name English
FEMA NO. 2976, DIHYDRATE-
Code English
QUININE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
QUININE HCL
Common Name English
QUININE HYDROCHLORIDE DIHYDRATE [MART.]
Common Name English
QUININE HYDROCHLORIDE [MART.]
Common Name English
QUININE MONOHYDROCHLORIDE DIHYDRATE
Common Name English
QUININE HYDROCHLORIDE [WHO-IP]
Common Name English
QUININE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
QUININE HYDROCHLORIDE DIHYDRATE [MI]
Common Name English
QUININE MONOHYDROCHLORIDE DIHYRATE
Common Name English
Quinine hydrochloride dihydrate [WHO-DD]
Common Name English
CHININUM MURIATICUM [HPUS]
Common Name English
Classification Tree Code System Code
JECFA EVALUATION QUININE HYDROCHLORIDE
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
CFR 21 CFR 310.547
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
Code System Code Type Description
RXCUI
9074
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY RxNorm
EVMPD
SUB15093MIG
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID2047694
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
MERCK INDEX
m9447
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY Merck Index
DRUG BANK
DBSALT001044
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
CAS
6119-47-7
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
PUBCHEM
16211283
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
FDA UNII
711S8Y0T33
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
NCI_THESAURUS
C75269
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
ChEMBL
CHEMBL170
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
RS_ITEM_NUM
1596807
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
DAILYMED
711S8Y0T33
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
QUININE HYDROCHLORIDE
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY Description: Silky, colourless crystals, often grouped in clusters; odourless. Solubility: Soluble in water; freely soluble in ethanol (~750 g/l) TS; very slightly soluble in ether R. Category: Antimalarial. Storage: Quinine hydrochloride should be kept in a well-closed container, protected from light. Additional information. Quinine hydrochloride has a very bitter taste. Definition: Quinine hydrochloride contains not less than 98.5% and not more than 101.0% of total alkaloids, calculated as C20H24N2O2,HCl and with reference to the dried substance.
SMS_ID
100000090455
Created by admin on Mon Mar 31 17:50:48 GMT 2025 , Edited by admin on Mon Mar 31 17:50:48 GMT 2025
PRIMARY
Related Record Type Details
Structure of QUININE
PARENT -> SALT/SOLVATE
Structure of QUININE HYDROCHLORIDE ANHYDROUS
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of HYDROQUININE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of QUINIDINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of CINCHONIDINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of QUININE
ACTIVE MOIETY
NIH
NCATS
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