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
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
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 |
|---|---|---|
| A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related Plant species. | 2001 Dec |
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| Adsorption geometry of modifiers as key in imparting chirality to platinum catalysts. | 2001 Nov 7 |
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| Adsorption mode of cinchonidine on Cu(111) surface. | 2002 Dec 4 |
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| Highly selective hydroformylation of the cinchona alkaloids. | 2002 Jul 12 |
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| In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand. | 2003 |
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| Hydrogenation of cinchona alkaloids over supported Pt catalyst. | 2003 |
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| Determination of enantiomeric excess using the ultraviolet-circular dichroism and the high-performance liquid chromatography-circular dichroism methods. | 2003 Jul |
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| Interaction between ketopantolactone and chirally modified Pt investigated by attenuated total reflection IR concentration modulation spectroscopy. | 2003 Nov 5 |
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| Chiral recognition of peptide enantiomers by cinchona alkaloid derived chiral selectors: mechanistic investigations by liquid chromatography, NMR spectroscopy, and molecular modeling. | 2003 Oct 31 |
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| Direct STM investigation of cinchona alkaloid adsorption on Cu(III). | 2004 Apr 13 |
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| Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine. | 2004 Apr 16 |
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| 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 |
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| Polymer-supported Cinchona alkaloid-derived ammonium salts as recoverable phase-transfer catalysts for the asymmetric synthesis of alpha-amino acids. | 2004 Apr 30 |
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| Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique. | 2004 May 5 |
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| Signaling molecularly imprinted polymers: molecular recognition-based sensing materials. | 2005 |
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| Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. | 2005 Aug 17 |
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| Screening of bitterness-suppressing agents for quinine: the use of molecularly imprinted polymers. | 2005 Feb |
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| Cobalt complexes with cinchonidine and quinidine: effect of C8/C9 stereochemistry and 6'-substitution on intermolecular interactions. | 2005 Feb |
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| Structure-property relationship in py-hexahydrocinchonidine diastereomers: ab initio and NMR study. | 2005 Feb 10 |
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| 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 |
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| Stereospecific oxidation of the (S)-enantiomer of RS-8359, a selective and reversible monoamine oxidase A (MAO-A) inhibitor, by aldehyde oxidase. | 2005 Jun |
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| 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 |
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| 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 |
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| Solvent-induced conformational changes of O-phenyl-cinchonidine: a theoretical and VCD spectroscopy study. | 2006 Jan 26 |
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| Liquid chromatographic analysis of cinchona alkaloids in beverages. | 2006 Jul-Aug |
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| Improved asymmetric S(N)Ar reaction of beta-dicarbonyl compounds catalyzed by quaternary ammonium salts derived from cinchona alkaloids. | 2006 Jun 23 |
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| Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS. | 2006 Mar 21 |
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| Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation. | 2006 Oct 27 |
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| Chirally modified platinum generated by adsorption of cinchonidine ether derivatives: towards uncovering the chiral sites. | 2007 |
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| Role of guiding groups in cinchona-modified platinum for controlling the sense of enantiodifferentiation in the hydrogenation of ketones. | 2007 Aug 29 |
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| Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces. | 2007 Dec 26 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| An improved synthesis of 10,11-didehydro Cinchona alkaloids. | 2008 Mar |
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| 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 |
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| 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 |
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:
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| Code System | Code | Type | Description | ||
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CINCHONIDINE
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485-71-2
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M3559
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207-622-3
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C041622
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1U622LRA8Z
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101744
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C75264
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SUB13374MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
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