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Details

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

SHOW SMILES / InChI
Structure of CINCHONIDINE

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

Description

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Quinimax
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Moleculary imprinted polymers with metalloporphyrin-based molecular recognition sites coassembled with methacrylic acid.
2001 Aug 15
An in situ attenuated total reflection infrared study of a chiral catalytic solid-liquid interface: cinchonidine adsorption on pt.
2001 Dec 5
Adsorption geometry of modifiers as key in imparting chirality to platinum catalysts.
2001 Nov 7
The enantioselective synthesis of alpha-amino acid derivatives via organoboranes.
2002 Aug 14
Highly selective hydroformylation of the cinchona alkaloids.
2002 Jul 12
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
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
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
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003 Sep 1
Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine.
2004 Apr 16
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
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
Competition at chiral metal surfaces: fundamental aspects of the inversion of enantioselectivity in hydrogenations on platinum.
2005 Jun 15
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
Michael reactions carried out using a bench-top flow system.
2006 Feb 7
Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS.
2006 Mar 21
Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals.
2006 Nov 2
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
Surface processes occurring on Rh/alumina during chiral modification by cinchonidine: an ATR-IR spectroscopy study.
2007 Jul 17
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
Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes.
2008 Aug
Conformational behavior of cinchonidine revisited: a combined theoretical and experimental study.
2008 Aug 7
Highly enantioselective synthesis of isoxazoline N-oxides.
2008 Feb 14
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
Influence of peripheral groups on the physical and chemical behavior of cinchona alkaloids.
2009 Aug 27
Construction of expression system of rabbit aldehyde oxidase cDNA for the clarification of species differences.
2009 Jul-Sep
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
Practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors: access to chiral beta-alkynyl acids.
2010 Jan 20
Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency.
2010 Mar 21
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
2011 Dec 15
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: intrarectally, IM
In Vitro Use Guide
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 Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
CAS
485-71-2
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
MERCK INDEX
M3559
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
207-622-3
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
MESH
C041622
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
PUBCHEM
101744
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
NCI_THESAURUS
C75264
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
EVMPD
SUB13374MIG
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY