Cytisine, also known as baptitoxine, cytisinicline, or sophorine, is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. It has been used medically to help with smoking cessation.[ and is being investigated in additional trials in the United States and a non-inferiority trial in Australia in which it is being compared head-to-head with the smoking cessation aid varenicline (sold in the United States as Chantix).]
Sources
Cytisine is extracted from the seeds of Cytisus laburnum L. (Golden Rain acacia), and is found in several genera of the subfamily Faboideae of the family Fabaceae, including Laburnum, Anagyris, Thermopsis, Cytisus, Genista, Retama and Sophora. Cytisine is also present in Gymnocladus of the subfamily Caesalpinioideae.
Uses
Smoking cessation
Cytisine has been available in post-Soviet states for more than 40 years as an aid to smoking cessation under the brand name Tabex from the Bulgarian pharmaceutical company Sopharma AD.
Its molecular structure has some similarity to that of nicotine, and it has similar pharmacological effects. Like the smoking cessation aid varenicline, cytisine is a partial agonist of nicotinic acetylcholine receptors (nAChRs).
In 2011, a randomized controlled trial with 740 patients found cytisine improved 12-month abstinence from nicotine from 2.4% with placebo to 8.4% with cytisine.
Recreational
Plants containing cytisine, including the scotch broom and mescalbean, have also been used recreationally. Positive effects are reported to include a nicotine-like intoxication.
Reagent for organic chemistry
laevorotary extracted from Laburnum anagyroides seeds was used as a starting material for the preparation of "dextrorotary sparteine surrogate", for the preparation of enriched lithium anions of opposite stereochemistry to those anions obtained from sparteine.
Toxicity
Cytisine has been found to interfere with breathing and cause death in test mice; i.v. in mice is about 2 mg/kg.[ The Merck Index, 10th Ed. (1983) p.402, Rahway: Merck & Co.] Cytisine is also teratogenic.
Māmane ( Sophora chrysophylla) can contain amounts of cytisine that are lethal to most animals. The palila ( Loxioides bailleui, a bird), Uresiphita polygonalis virescens and Cydia species (), and possibly Domestic sheep and are not affected by the toxin for various reasons, and consume māmane, or parts of it, as food. U. p. virescens caterpillars are possibly able to sequester the cytisine to give themselves protection from predation; they have Aposematism coloration which would warn off potential .
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