cinchonine

Cinchonine is a naturally occurring **alkaloid** found primarily in the bark of *Cinchona* species such as *Cinchona officinalis*[3][6]. Historically, it was used as an **antimalarial agent** due to its ability to inhibit heme polymerase within the malaria parasite, Plasmodium, disrupting the parasite's detoxification process and leading to its death[1]. Its pharmacological properties include **anti-inflammatory**, **analgesic**, **antipyretic**, **antioxidant**, and **antiarrhythmic effects**; these are attributed to its action on ion channels, inhibition of inflammatory mediator synthesis, and modulation of neurotransmitter systems[1]. In addition to medical uses, cinchonine serves as a crucial **chiral catalyst** in asymmetric synthesis within organic chemistry, enabling the production of enantiomerically pure compounds[3][4]. Structurally, cinchonine is a stereoisomer and pseudo-enantiomer of cinchonidine[3][6], with molecular formula C19H22N2O. Its primary indications are antimalarial and, to a lesser extent, analgesic and anti-inflammatory uses. It is mostly supplanted by more potent antimalarials but remains relevant for chemical synthesis and research.

Other names

(+)-cinchonineD-cinchoninecinchonincinchonin base(8R,9S)-cinchoninecinchonanan-9-olcinchonanan9-olcinchonanan 9-ol(9S)-cinchonan-9-ol