Cinchonidine

Structural formula
General
Surname	Cinchonidine
other names	(8 S , 9 R ) -quinchonan-9-ol; (-) - Quinolin-4-yl- (5-vinyl-1-aza-bicyclo [2.2.2] oct-2-yl) -methanol; (-) - cinchonidine;
Molecular formula	C 19 H 22 N 2 O
Brief description	colorless, crystalline solid
External identifiers / databases
EC number	207-622-3
ECHA InfoCard	100.006.930
PubChem	101744
ChemSpider	91930
Wikidata	Q412713
properties
Molar mass	294.39 g mol −1
Physical state	firmly
Melting point	205 ° C
solubility	poor in water (0.25 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: 261-262-301 + 312
Toxicological data	206 mg kg −1 ( LD 50 , rat , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cinchonidine belongs to the group of china alkaloids . Like most alkaloids, it is physiologically active and is a plant poison.

Occurrence

(-) - Cinchonidine and the isomer (+) - cinchonine occur naturally in the bark of cinchona trees (mainly Cinchona ledgeriana ) and can be extracted from it .

Quinoline alkaloids, including (-) - cinchonidine, are found in the bark of the cinchona tree.

Chemical properties and use

When light and air are excluded, the colorless, sparingly water-soluble substance is stable; Under the influence of light and oxidizing agents , cinchonidine is decomposed or oxidized to yellowish colored products. When cinchonine is distilled with potassium hydroxide , quinoline is formed.

(-) - Cinchonidine is used to resolve racemates . It forms diastereomeric salts with racemic acids , which can be separated by fractional crystallization. (-) - Cinchonidine is one of the cinchona alkaloid catalysts which, as chiral amines, are Lewis bases . These catalytic reactions are in the org. Chemistry can be used in many ways. An example of this is the 1,4-addition reaction according to Wynberg .

safety instructions

In animal experiments with rats, an LD ₅₀ value of 206 mg / kg was determined for (-) - cinchonidine given intraperitoneally . Even at sublethal doses, the animals were less active or drowsy and showed muscle tremors and cramps .

Individual evidence

↑ ^a ^b ^c ^d Datasheet Cinchonidine (PDF) from Carl Roth , accessed on May 9, 2017.
↑ Data sheet (-) - Cinchonidine (PDF) from Merck , accessed on March 23, 2011.
↑ ^a ^b Entry on cinchonidine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b Acta Pharmacologica et Toxicologica , 1948 , Vol. 4, p. 265.
↑ Daunderer: Clinical Toxicology, Cinchonidin ffl-443 ; 69th result. 8.91.
^ ^A ^b Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 495, ISBN 978-3-906390-29-1 .
↑ Entry on cinchonidine at ChemicalBook , accessed September 4, 2010.
↑ Lueger, Otto; In: Lexicon of total technology , 1904, pp. 142–146.
↑ LFFieser, M. Fieser; In: Textbook of Organic Chemistry ; 3rd edition, Verlag Chemie, 1957, p. 300.
^ HJ Wynberg; In: J. Am. Chem. Soc. , 1981 , 103 , pp. 417-430.

[Roth-1] Datasheet Cinchonidine (PDF) from Carl Roth , accessed on May 9, 2017.

[Merck-2] Data sheet (-) - Cinchonidine (PDF) from Merck , accessed on March 23, 2011.

[chemid-3] Entry on cinchonidine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Acta-4] Acta Pharmacologica et Toxicologica , 1948 , Vol. 4, p. 265.

[5] Daunderer: Clinical Toxicology, Cinchonidin ffl-443 ; 69th result. 8.91.

[Gossauer-6] A ^b Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 495, ISBN 978-3-906390-29-1 .

[7] Entry on cinchonidine at ChemicalBook , accessed September 4, 2010.

[8] Lueger, Otto; In: Lexicon of total technology , 1904, pp. 142–146.

[9] LFFieser, M. Fieser; In: Textbook of Organic Chemistry ; 3rd edition, Verlag Chemie, 1957, p. 300.

[10] HJ Wynberg; In: J. Am. Chem. Soc. , 1981 , 103 , pp. 417-430.