CINCHONIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H22N2O
Molecular Weight	294.3908
Optical Activity	( - )
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H]([C@@H]1C[C@@H]2CC[N@]1C[C@@H]2C=C)C3=C4C=CC=CC4=NC=C3

InChI

InChIKey=KMPWYEUPVWOPIM-KODHJQJWSA-N

InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H22N2O
Molecular Weight	294.3908
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.medicatione.com/?c=drug&s=quinimax
Curator's Comment: Description was created based on several sources, including http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500012185.pdf https://www.ncbi.nlm.nih.gov/pubmed/9776305

Cinchonidine is an alkaloid found in Cinchona officinalis and Gongronema latifolium. Cinchonidine is an antimalarial drug which has been used clinically in malaria caused by Plasmodium falciparum. Cinchonidine is reported as an ingredient of Quinimax in a number of countries. Quinimax is a combination of four alkaloids (quinine, quinidine, cinchoine and cinchonidine).

Approval Year

Targets

Primary Target	Pharmacology	Potency
Plasmodium falciparum 75 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15508779	Inhibitor 8504	225.0 nM [EC50]
Trypanosoma brucei brucei 12 Target ID: CHEMBL612851 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23816880	Inhibitor 8504
Leishmania mexicana mexicana 8 Target ID: CHEMBL613214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23816880	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Malaria 96 Sources: http://www.ndrugs.com/?s=quinimax	Primary		Approved 8583	Quinimax Approved Use Indications: malaria

PubMed

Title	Date	PubMed
Chiral recognition in cinchona alkaloid protonated dimers: mass spectrometry and UV photodissociation studies.	2010-03-11	20058939
Platinum nanoparticles: the crucial role of crystal face and colloid stabilizer in the diastereoselective hydrogenation of cinchonidine.	2010-02-15	20039346
Synthesis and biological activity of the calcium modulator (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.	2010-02-01	20064722
Preparative resolution of etodolac enantiomers by preferential crystallization method.	2009-10	19898806
Experimental and theoretical analysis of asymmetric induction in heterogeneous catalysis: diastereoselective hydrogenation of chiral alpha-hydroxyketones over Pt catalyst.	2009-04-01	19260682
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.	2009-02	19107468
Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.	2008-10-01	18774816
A combined NMR, DFT, and X-ray investigation of some cinchona alkaloid O-ethers.	2008-09-05	18683975
Conformational behavior of cinchonidine revisited: a combined theoretical and experimental study.	2008-08-07	18636698
Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones.	2008-08-01	18572922
Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare.	2008-03	19325758
Highly enantioselective synthesis of isoxazoline N-oxides.	2008-02-14	18478708
Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids.	2008-01	17966123
Phthalocyanine-based molecularly imprinted polymers as nucleoside receptors.	2008	18288245
Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces.	2007-12-26	18044897
Pilot feasibility study of an emergency paediatric kit for intra-rectal quinine administration used by the personnel of community-based health care units in Senegal.	2007-11-15	18005442
Role of guiding groups in cinchona-modified platinum for controlling the sense of enantiodifferentiation in the hydrogenation of ketones.	2007-08-29	17676845
Diastereo- and enantioselective synthesis of alpha,beta-epoxyketones using aqueous NaOCl in conjunction with dihydrocinchonidine derived phase-transfer catalysis at room temperature. Scope and limitations.	2007-07-21	17609760
Acceptability and efficacy of intra-rectal quinine alkaloids as a pre-transfer treatment of non-per os malaria in peripheral health care facilities in Mopti, Mali.	2007-05-22	17519031
Enantioselective hydrogenation of ethyl pyruvate over diop modified Pt nanoclusters. Determination of geometry of the ligand adsorption mode via DRIFTS.	2007-02-21	17287883
Chirally modified platinum generated by adsorption of cinchonidine ether derivatives: towards uncovering the chiral sites.	2007	17763490
Competitive chemisorption between pairs of cinchona alkaloids and related compounds from solution onto platinum surfaces.	2006-12-27	17177346
Effect of protonation on the conformation of cinchonidine.	2006-12-13	17147361
Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals.	2006-11-02	17064139
Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation.	2006-10-27	17064051
Cinchonidine adsorption on gold and gold-containing bimetallic platinum metal surfaces: an attenuated total reflection infrared and density functional theory study.	2006-08-31	16928003
Liquid chromatographic analysis of cinchona alkaloids in beverages.	2006-08-19	16915843
Improved asymmetric S(N)Ar reaction of beta-dicarbonyl compounds catalyzed by quaternary ammonium salts derived from cinchona alkaloids.	2006-06-23	16776530
Species differences in enantioselective 2-oxidations of RS-8359, a selective and reversible MAO-A inhibitor, and cinchona alkaloids by aldehyde oxidase.	2006-04	16400710
The origin of chemo- and enantioselectivity in the hydrogenation of diketones on platinum.	2006-03-29	16551114
Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS.	2006-03-21	16633613
Michael reactions carried out using a bench-top flow system.	2006-02-07	16446807
Enantioseparation of secondary alcohols by diastereoisomeric salt formation.	2006-02	16385616
Competition at chiral metal surfaces: fundamental aspects of the inversion of enantioselectivity in hydrogenations on platinum.	2005-06-15	15941281
Stereospecific oxidation of the (S)-enantiomer of RS-8359, a selective and reversible monoamine oxidase A (MAO-A) inhibitor, by aldehyde oxidase.	2005-06	16192108
Screening of bitterness-suppressing agents for quinine: the use of molecularly imprinted polymers.	2005-02	15614815
Study of fragmentation pattern and adsorption of 9-O-(triphenylsilyl)-10,11-dihydrocinchonidine on platinum by hydrogen/deuterium exchange using electrospray ionization ion-trap tandem mass spectrometry.	2005	16308850
Large-scale synthesis and resolution of TRISPHAT [tris(tetrachlorobenzenediolato) phosphate(V)] anion.	2004-11-26	15549835
Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique.	2004-05-05	15093176
Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine.	2004-04-16	15074944
Interaction between ketopantolactone and chirally modified Pt investigated by attenuated total reflection IR concentration modulation spectroscopy.	2003-11-05	14583014
Conformational spaces of Cinchona alkaloids.	2003-08	12840830
New crystalline complex of quinine and quinidine.	2003-03-20	12643316
Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s.	2003-02	12697166
[Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers].	2002-09	16358696
The enantioselective synthesis of alpha-amino acid derivatives via organoboranes.	2002-08-14	12167010
Highly selective hydroformylation of the cinchona alkaloids.	2002-07-12	12098330
Enantioselective hydrogenation over cinchona-modified Pt: the special role of carboxylic acids.	2002-03-15	11921227
Adsorption geometry of modifiers as key in imparting chirality to platinum catalysts.	2001-11-07	11686738
HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations.	2001-04	11345710

Patents

Sample Use Guides

In Vivo Use Guide

Fifty-five children were given 20 mg/kg of the diluted injectable form of Quinimax (a quinine, quinidine, cinchonine, cinchonidine association) intrarectally. A further 11 children with malaria were treated with 12.5 mg/kg of the same Quinimax solution by the intramuscular route. All the children were treated twice a day for 3 d.

Route of Administration: Other

In Vitro Use Guide

Cinchonidine inhibited P. falcifarum with IC₅₀=0.28 ug/ml

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:22:57 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:57 GMT 2025`
Record UNII	1U622LRA8Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CINCHONIDINE

Common Name

English

CINCHONIDINE [WHO-IP]

Preferred Name

English

CINCHONIDINE [MI]

Common Name

English

QUININE BISULFATE IMPURITY B [WHO-IP]

Common Name

English

Cinchonidine [WHO-DD]

Common Name

English

QUININE SULFATE IMPURITY B [EP IMPURITY]

Common Name

English

QUININE BISULFATE HEPTAHYDRATE IMPURITY B [WHO-IP]

Common Name

English

.ALPHA.-QUINIDINE

Common Name

English

QUININE HYDROCHLORIDE IMPURITY B [EP IMPURITY]

Common Name

English

CINCHOVATINE-

Common Name

English

NSC-5364

Code

English

QUININE SULFATE IMPURITY B [WHO-IP]

Common Name

English

(R)-((2S,4S,5R)-5-ETHENYL-1-AZABICYCLO(2.2.2)OCT-2-YL)(QUINOLIN-4-YL)METHANOL [WHO-IP]

Systematic Name

English

Code System Code Type Description

NSC

5364