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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22N2O.2ClH
Molecular Weight 367.313
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHONIDINE DIHYDROCHLORIDE

SMILES

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

InChI

InChIKey=ZDBQDNUZNQOCTH-WESSAKMQSA-N
InChI=1S/C19H22N2O.2ClH/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;2*1H/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

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

Description
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

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Quinimax

Approved Use

Indications: malaria
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations.
2001 Apr
A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related Plant species.
2001 Dec
Adsorption geometry of modifiers as key in imparting chirality to platinum catalysts.
2001 Nov 7
Enantioselective hydrogenation over cinchona-modified Pt: the special role of carboxylic acids.
2002 Mar 15
[Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers].
2002 Sep
Hydrogenation of cinchona alkaloids over supported Pt catalyst.
2003
Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s.
2003 Feb
The characterisation of supported platinum nanoparticles on carbon used for enantioselective hydrogenation: a combined electrochemical-STM approach.
2003 Feb 17
Highly stereoselective, uniformly sized molecularly imprinted polymers for cinchona alkaloids in hydro-organic mobile phases.
2003 Jan
Determination of enantiomeric excess using the ultraviolet-circular dichroism and the high-performance liquid chromatography-circular dichroism methods.
2003 Jul
Preparation of enantiopure 1-azabicyclo[3.2.2]nonanes functionalized at carbon C3, from cinchonine and cinchonidine. stereoselective solvolysis and an easily enolizable ketone.
2003 Jun 13
Interaction between ketopantolactone and chirally modified Pt investigated by attenuated total reflection IR concentration modulation spectroscopy.
2003 Nov 5
Chiral recognition of peptide enantiomers by cinchona alkaloid derived chiral selectors: mechanistic investigations by liquid chromatography, NMR spectroscopy, and molecular modeling.
2003 Oct 31
Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine.
2004 Apr 16
Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique.
2004 May 5
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
Competition at chiral metal surfaces: fundamental aspects of the inversion of enantioselectivity in hydrogenations on platinum.
2005 Jun 15
Species differences in enantioselective 2-oxidations of RS-8359, a selective and reversible MAO-A inhibitor, and cinchona alkaloids by aldehyde oxidase.
2006 Apr
Cinchonidine adsorption on gold and gold-containing bimetallic platinum metal surfaces: an attenuated total reflection infrared and density functional theory study.
2006 Aug 31
Competitive chemisorption between pairs of cinchona alkaloids and related compounds from solution onto platinum surfaces.
2006 Dec 27
Enantioseparation of secondary alcohols by diastereoisomeric salt formation.
2006 Feb
Michael reactions carried out using a bench-top flow system.
2006 Feb 7
Liquid chromatographic analysis of cinchona alkaloids in beverages.
2006 Jul-Aug
Improved asymmetric S(N)Ar reaction of beta-dicarbonyl compounds catalyzed by quaternary ammonium salts derived from cinchona alkaloids.
2006 Jun 23
Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals.
2006 Nov 2
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 Jul 21
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 May 22
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 Nov 15
Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones.
2008 Aug 1
Conformational behavior of cinchonidine revisited: a combined theoretical and experimental study.
2008 Aug 7
Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare.
2008 Mar
Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.
2008 Oct 1
A combined NMR, DFT, and X-ray investigation of some cinchona alkaloid O-ethers.
2008 Sep 5
Experimental and theoretical analysis of asymmetric induction in heterogeneous catalysis: diastereoselective hydrogenation of chiral alpha-hydroxyketones over Pt catalyst.
2009 Apr 1
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 Feb
Preparative resolution of etodolac enantiomers by preferential crystallization method.
2009 Oct
A single amino acid substitution confers high cinchonidine oxidation activity comparable with that of rabbit to monkey aldehyde oxidase 1.
2010 Feb
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 Feb 1
Chiral recognition in cinchona alkaloid protonated dimers: mass spectrometry and UV photodissociation studies.
2010 Mar 11
Patents

Sample Use Guides

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
Cinchonidine inhibited P. falcifarum with IC₅₀=0.28 ug/ml
Substance Class Chemical
Created
by admin
on Thu Jul 06 12:17:57 UTC 2023
Edited
by admin
on Thu Jul 06 12:17:57 UTC 2023
Record UNII
QNY56C6XYZ
Record Status Validated (UNII)
Record Version
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Name Type Language
CINCHONIDINE DIHYDROCHLORIDE
MI   WHO-DD  
Common Name English
CINCHONIDINE DIHYDROCHLORIDE [MI]
Common Name English
Cinchonidine dihydrochloride [WHO-DD]
Common Name English
CINCHONAN-9-OL, DIHYDROCHLORIDE, (8.ALPHA.,9R)-
Common Name English
Code System Code Type Description
CAS
524-54-9
Created by admin on Thu Jul 06 12:17:57 UTC 2023 , Edited by admin on Thu Jul 06 12:17:57 UTC 2023
PRIMARY
EVMPD
SUB125748
Created by admin on Thu Jul 06 12:17:57 UTC 2023 , Edited by admin on Thu Jul 06 12:17:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID70200414
Created by admin on Thu Jul 06 12:17:57 UTC 2023 , Edited by admin on Thu Jul 06 12:17:57 UTC 2023
PRIMARY
PUBCHEM
45073521
Created by admin on Thu Jul 06 12:17:57 UTC 2023 , Edited by admin on Thu Jul 06 12:17:57 UTC 2023
PRIMARY
SMS_ID
100000146237
Created by admin on Thu Jul 06 12:17:57 UTC 2023 , Edited by admin on Thu Jul 06 12:17:57 UTC 2023
PRIMARY
FDA UNII
QNY56C6XYZ
Created by admin on Thu Jul 06 12:17:57 UTC 2023 , Edited by admin on Thu Jul 06 12:17:57 UTC 2023
PRIMARY
MERCK INDEX
M3559
Created by admin on Thu Jul 06 12:17:57 UTC 2023 , Edited by admin on Thu Jul 06 12:17:57 UTC 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY