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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:: 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
Highly selective hydroformylation of the cinchona alkaloids.
2002 Jul 12
Enantioselective hydrogenation over cinchona-modified Pt: the special role of carboxylic acids.
2002 Mar 15
New crystalline complex of quinine and quinidine.
2002 Nov-Dec
[Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers].
2002 Sep
In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand.
2003
Conformational spaces of Cinchona alkaloids.
2003 Aug
Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s.
2003 Feb
Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens.
2003 Jan
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
Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine.
2004 Apr 16
Large-scale synthesis and resolution of TRISPHAT [tris(tetrachlorobenzenediolato) phosphate(V)] anion.
2004 Nov 26
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
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
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
Cinchonidine adsorption on gold and gold-containing bimetallic platinum metal surfaces: an attenuated total reflection infrared and density functional theory study.
2006 Aug 31
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
Solvent-induced conformational changes of O-phenyl-cinchonidine: a theoretical and VCD spectroscopy study.
2006 Jan 26
The origin of chemo- and enantioselectivity in the hydrogenation of diketones on platinum.
2006 Mar 29
Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals.
2006 Nov 2
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
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
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
Highly enantioselective synthesis of isoxazoline N-oxides.
2008 Feb 14
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
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
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
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
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
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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