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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22N2O
Molecular Weight 294.3915
Optical Activity ( - )
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHONIDINE

SMILES

C=C[C@@]1([H])CN2CC[C@@]1([H])C[C@@]2([H])[C@@]([H])(c3ccnc4ccccc34)O

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

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
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
Adsorption mode of cinchonidine on Cu(111) surface.
2002 Dec 4
Highly selective hydroformylation of the cinchona alkaloids.
2002 Jul 12
In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand.
2003
Hydrogenation of cinchona alkaloids over supported Pt catalyst.
2003
Determination of enantiomeric excess using the ultraviolet-circular dichroism and the high-performance liquid chromatography-circular dichroism methods.
2003 Jul
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
Direct STM investigation of cinchona alkaloid adsorption on Cu(III).
2004 Apr 13
Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine.
2004 Apr 16
Efficient synthesis of 4-(3'-furanyl)butenolide derivatives via PdII-catalyzed oxidative heterodimeric cyclization reaction of 2,3-allenoic acids and 1,2-allenyl ketones.
2004 Apr 19
Polymer-supported Cinchona alkaloid-derived ammonium salts as recoverable phase-transfer catalysts for the asymmetric synthesis of alpha-amino acids.
2004 Apr 30
Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique.
2004 May 5
Signaling molecularly imprinted polymers: molecular recognition-based sensing materials.
2005
Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids.
2005 Aug 17
Screening of bitterness-suppressing agents for quinine: the use of molecularly imprinted polymers.
2005 Feb
Cobalt complexes with cinchonidine and quinidine: effect of C8/C9 stereochemistry and 6'-substitution on intermolecular interactions.
2005 Feb
Structure-property relationship in py-hexahydrocinchonidine diastereomers: ab initio and NMR study.
2005 Feb 10
Role of the solvent in the adsorption-desorption equilibrium of cinchona alkaloids between solution and a platinum surface: correlations among solvent polarity, cinchona solubility, and catalytic performance.
2005 Jan 13
Stereospecific oxidation of the (S)-enantiomer of RS-8359, a selective and reversible monoamine oxidase A (MAO-A) inhibitor, by aldehyde oxidase.
2005 Jun
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
Effect of protonation on the conformation of cinchonidine.
2006 Dec 13
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
Solvent-induced conformational changes of O-phenyl-cinchonidine: a theoretical and VCD spectroscopy study.
2006 Jan 26
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
Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS.
2006 Mar 21
Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation.
2006 Oct 27
Chirally modified platinum generated by adsorption of cinchonidine ether derivatives: towards uncovering the chiral sites.
2007
Role of guiding groups in cinchona-modified platinum for controlling the sense of enantiodifferentiation in the hydrogenation of ketones.
2007 Aug 29
Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces.
2007 Dec 26
Enantioselective hydrogenation of ethyl pyruvate over diop modified Pt nanoclusters. Determination of geometry of the ligand adsorption mode via DRIFTS.
2007 Feb 21
Surface processes occurring on Rh/alumina during chiral modification by cinchonidine: an ATR-IR spectroscopy study.
2007 Jul 17
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
Phase-transfer-catalyzed asymmetric acylimidazole alkylation.
2007 Nov 8
Phthalocyanine-based molecularly imprinted polymers as nucleoside receptors.
2008
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
An improved synthesis of 10,11-didehydro Cinchona alkaloids.
2008 Mar
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
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
Platinum nanoparticles: the crucial role of crystal face and colloid stabilizer in the diastereoselective hydrogenation of cinchonidine.
2010 Feb 15
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
Name Type Language
CINCHONIDINE
MI   WHO-DD   WHO-IP  
Common Name English
CINCHONIDINE [MI]
Common Name English
CINCHONIDINE [WHO-DD]
Common Name English
QUININE BISULFATE IMPURITY B [WHO-IP]
Common Name English
QUININE BISULFATE HEPTAHYDRATE IMPURITY B [WHO-IP]
Common Name English
.ALPHA.-QUINIDINE
Common Name English
QUININE SULFATE IMPURITY B [EP]
Common Name English
QUININE HYDROCHLORIDE IMPURITY B [EP]
Common Name English
CINCHOVATINE-
Common Name English
CINCHONIDINE [WHO-IP]
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
WIKIPEDIA
CINCHONIDINE
Created by admin on Sat Jun 26 09:36:01 UTC 2021 , Edited by admin on Sat Jun 26 09:36:01 UTC 2021
PRIMARY
CAS
485-71-2
Created by admin on Sat Jun 26 09:36:01 UTC 2021 , Edited by admin on Sat Jun 26 09:36:01 UTC 2021
PRIMARY
MERCK INDEX
M3559
Created by admin on Sat Jun 26 09:36:01 UTC 2021 , Edited by admin on Sat Jun 26 09:36:01 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
207-622-3
Created by admin on Sat Jun 26 09:36:01 UTC 2021 , Edited by admin on Sat Jun 26 09:36:01 UTC 2021
PRIMARY
MESH
C041622
Created by admin on Sat Jun 26 09:36:01 UTC 2021 , Edited by admin on Sat Jun 26 09:36:01 UTC 2021
PRIMARY
FDA UNII
1U622LRA8Z
Created by admin on Sat Jun 26 09:36:01 UTC 2021 , Edited by admin on Sat Jun 26 09:36:01 UTC 2021
PRIMARY
PUBCHEM
101744
Created by admin on Sat Jun 26 09:36:01 UTC 2021 , Edited by admin on Sat Jun 26 09:36:01 UTC 2021
PRIMARY
NCI_THESAURUS
C75264
Created by admin on Sat Jun 26 09:36:01 UTC 2021 , Edited by admin on Sat Jun 26 09:36:01 UTC 2021
PRIMARY
EVMPD
SUB13374MIG
Created by admin on Sat Jun 26 09:36:01 UTC 2021 , Edited by admin on Sat Jun 26 09:36:01 UTC 2021
PRIMARY