2289. Cinchotoxine

Nomenclature

CAS number: 69-24-9
(3R-cis)-3-(3-Ethenyl-4-piperidinyl)-1-(4-quinolinyl)-1-propanone; 9-deoxy-9-oxo-1,8-secocinchonine; cinchonicine.
C19H22N2O; mol wt 294.39.
C 77.52%, H 7.53%, N 9.52%, O 5.43%.

Description and references

A rearrangement product of cinchonine or cinchonidine obtained by boiling with acetic acid: Pasteur, Compt. Rend. 37, 110 (1853). Miller, Rohde, Ber. 33, 3214 (1900). Conversion to cinchonidinone and cinchonine: Rabe, Ber. 44, 2088 (1911); 41, 62 (1908). Prepn from cinchonine: Prostenik, Prelog, Helv. Chim. Acta 26, 1965 (1943).

Chemical structure

Properties

Bitter needles. mp 58-60°. [α]D15 +47° in alcohol. Sparingly sol in water; sol in alcohol, ether, chloroform.