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
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
| 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 |
DescriptionCurator'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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| Adsorption mode of cinchonidine on Cu(111) surface. | 2002 Dec 4 |
|
| New crystalline complex of quinine and quinidine. | 2002 Nov-Dec |
|
| 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 |
|
| 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 |
|
| The characterisation of supported platinum nanoparticles on carbon used for enantioselective hydrogenation: a combined electrochemical-STM approach. | 2003 Feb 17 |
|
| Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens. | 2003 Jan |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique. | 2004 May 5 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS. | 2006 Mar 21 |
|
| 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 |
|
| Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces. | 2007 Dec 26 |
|
| Cinchonidinium chloride monohydrate. | 2007 Dec 6 |
|
| 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 |
|
| 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 |
|
| An improved synthesis of 10,11-didehydro Cinchona alkaloids. | 2008 Mar |
|
| 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 |
|
| 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 |
|
| Platinum nanoparticles: the crucial role of crystal face and colloid stabilizer in the diastereoselective hydrogenation of cinchonidine. | 2010 Feb 15 |
|
| Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency. | 2010 Mar 21 |
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
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
QNY56C6XYZ
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| Record Status |
Validated (UNII)
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| Record Version |
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PARENT -> SALT/SOLVATE |
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