Quinoline alkaloids

Quinine is a medication used to treat malaria and babesiosis. This includes the treatment of malaria due to Plasmodium falciparum that is resistant to chloroquine when artesunate is not available. While sometimes used for nocturnal leg cramps, quinine is not recommended for this purpose due to the risk of serious side effects. It can be taken by mouth or intravenously. Malaria resistance to quinine occurs in certain areas of the world. Quinine is also used as an ingredient in tonic water and other beverages to impart a bitter taste.

Quinidine is a class IA antiarrhythmic agent used to treat heart rhythm disturbances. It is a diastereomer of antimalarial agent quinine, originally derived from the bark of the cinchona tree. The drug causes increased action potential duration, as well as a prolonged QT interval. As of 2019, its IV formulation is no longer being manufactured for use in the United States.

Brucine is an alkaloid closely related to strychnine, most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is more toxic than brucine. In chemical synthesis, it can be used as a tool for stereospecific chemical syntheses.

Ergine, also known as lysergic acid amide (LSA or LAA) as well as LA-111, is a psychoactive compound of the ergoline and lysergamide families related to lysergic acid diethylamide (LSD). Ergine is an ergoline alkaloid found in fungi such as Claviceps paspali (ergot) and Periglandula species such as Periglandula clandestina, which are permanently connected with many morning glory vines. Ergine induces relatively mild psychedelic effects as well as pronounced sedative effects.

Ergoline is a core structure in many alkaloids and their synthetic derivatives. Ergoline alkaloids were first characterized in ergot. Some of these are implicated in the condition of ergotism, which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000 kg of all ergopeptines and 10,000–15,000 kg of lysergic acid, used primarily in the manufacture of semi-synthetic derivatives.

Cinchonine is an alkaloid found in Cinchona officinalis. It is used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo-enantiomer of cinchonidine.

Lycorine is a toxic crystalline alkaloid found in various Amaryllidaceae species, such as the cultivated bush lily (Clivia miniata), surprise lilies (Lycoris), and daffodils (Narcissus). It may be highly poisonous, or even lethal, when ingested in certain quantities. Regardless, it is sometimes used medicinally, a reason why some groups may harvest the very popular Clivia miniata.

Camptothecin (CPT) is a topoisomerase inhibitor. It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of natural products for anticancer drugs. It was isolated from the bark of Camptotheca acuminata (喜树 "Happy tree"), a tree native to China used in traditional Chinese medicine. It has been used clinically in China for the treatment of gastrointestinal tumors. CPT showed anticancer activity in preliminary clinical trials, especially against breast, ovarian, colon, lung, and stomach cancers. However, it has low solubility and adverse effects have been reported when used

Cinchonidine is an alkaloid found in Cinchona officinalis and Gongronema latifolium. It is used in asymmetric synthesis in organic chemistry.

Sanguinarine is a polycyclic quaternary alkaloid. It is extracted from some plants, including the bloodroot plant (Sanguinaria canadensis, from whose scientific name its name is derived), the Mexican prickly poppy (Argemone mexicana), Chelidonium majus, and Macleaya cordata.

Evoxine (haploperine) is a furoquinoline alkaloid with hypnotic and sedative effects. It is found naturally in a variety of Australian and African plants including Evodia xanthoxyloides and Teclea gerrardii.

Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.

Dihydrosanguinarine is an alkaloid found in the herbs Corydalis adunca and Lamprocapnos spectabilis. It gets its name from the Sanguinaria canadensis plant in the poppy family Papaveraceae in which it is also found.

Vinflunine (INN, trade name Javlor) is a novel fluorinated vinca alkaloid derivative undergoing research for the treatment of bladder cancer. It was originally discovered by the team of the Professor Jean-Claude Jacquesy (UMR CNRS 6514 – Poitiers University), developed by Laboratoires Pierre Fabre and was licensed to Bristol-Myers Squibb for development in certain countries, including the United States.

Dihydroquinine, also known as hydroquinine or DHQ, is an organic compound and as a cinchona alkaloid closely related to quinine. The specific rotation is −148° in ethanol. A derivative of this molecule is used as chiral ligand in the AD-mix for Sharpless dihydroxylation.

Bufothionine is a sulfur-containing compound which is present in the bufotoxins secreted by the parotoid gland of certain toads of the genera Bufo and Chaunus. The structure has been shown by X-ray crystallography to be (1,3,4,5-tetrahydro-5,5-dimethylpyrrolo-[4,3,2-de]quinolinio)-6-sulfate. This specific compound can be found in the skin of certain species of toad such as the Asiatic Toad, Chaunus arunco, Chaunus crucifer, Chaunus spinulosus, and Chaunus arenarum.

Norzoanthamine is an alkaloid found in soft corals of the genus Zoanthus

Haematopodin is the more stable breakdown product of Haematopodin B. Both compounds are found in the mushroom Mycena haematopus, although haematopodin only occurs in trace amounts in fresh fruit bodies. Similar pigments (with the 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline structure), known as batzellins and damirones, have been found in sea sponges. A chemical synthesis for haematopodin was reported in 1996. Key steps in the synthesis involved the addition of 3-[(2,4-dimethoxybenzyl)amino]-1-propanol to the indolo-6,7-quinone and cyclization of the resulting adduct with trifluoroacetic acid.

Nitidine is a benzophenanthridine alkaloid found in species of the genus Zanthoxylum , notably in Zanthoxylum nitidum. This compound has an anti-malarial activity.

Corynoline is an acetylcholinesterase inhibitor isolated from Corydalis incisa.

Tortuosamine is an alkaloid found in Sceletium tortuosum. Tortuosamine is a Serotonin reuptake inhibitor (SRI). Tortuosamine is a MAO-B inhibitor, that means it blocks the enzyme that breaks down dopamine in the brain resulting in increased dopamine levels when consumed, either orally, smoked, or snorted. The 3 other main alkaloids found in Sceletium tortuosum are, Mesembrine, Mesembrenone, and Mesembranol.