Cytisine

Other Names Baptitoxin, CYtiton, laburnin, 1,2,3,4,5,6-hexahydro8H- 1,5-methano-pyrido[1,2a] [1,5]diazocin-8-ol, sophorin, ulexin Substance type: quinolizidine alkaloid, lupine alkaloid Cytisine is found in numerous legumes (Leguminosae) (Plugge 1895), such as the rain shower tree (Laburnum anagyroides Medikus [syn. Cytisus laburnum 1.] ).497 Since cytisine acts to stimulate the central nervous system, states of excitation and confusion (with hallucinations, delirium), muscle spasms, as well as general clonic-tonic spasms in the extremities not infrequently occur. (Roth et al. 1994,443*) Cytisine docks to the acetylcholine (ACh) receptors of the central nervous system, the ganglia, and the neuromuscular endplate. The ganglia-blocking effects of cytisine are similar to those of nicotine and can induce strychninelike spasms, especially hallucinations, and even unconsciousness and ultimately death. However, the lethal dosage for humans is unknown (Roth et al. 1994, 801 f. *). The nicotine-like effects also explain the ethnopharmacological use of plants containing cytisine as tobacco substitutes. Other lupine alkaloids and cytisine derivatives have been found in many plants from the Family Leguminosae, including Lupinus spp. and Echinosophora koreensis Nakai (a close relative of the genus Sophora) (Murakoshi et al. 1977). Plants Containing Cytisine (from Bock 1994,75 ff.*; Rompp 1995*; Roth et al. 1994*; supplemented) Stock Plant Distribution Ammodendron spp.   Anagyris spp. southern Europe Baptisia spp. North America Colutea.arborescens 1. Mediterranean region Calutea spp. southeastern Europe, Asia Minor Cytisus canariensis Canary Islands, Mexico Cytisus spp. Europe Eucresta spp. Australia Genista germanica 1. central Europe Genista tinctoria 1. Europe Labttrnum alpinum (Mill.) Bercht.et Presl Alps, southern Europe [syn. Cytisus alpinusMill.]   Laburnum anagyroides Medik. [syn. Laburnum vulgare central and southern Europe Bercht.et Pres!' Cytisus laburnum 1.]   Lamprolobium fruticosumBenth. Australia Lampralobium grandiflorum Everist Australia Hovea acutifalia Cunn. Australia Hoveaspp. Australia Plagiocarpus axiUaris Benth. Australia Sophora secundiflora Mexico, Texas Sophora tomentosa 1. Australia, Oceania Spartium junceum 1. Spain, southern Europe Strongylodon macrobotrys A.Gray Philippines Templetonia spp. Australia Thel'mopsis spp. Australia Ulex europaeus 1. central Europe

Commercial Forms and Regulations Cytisine is sold in its pure form and is not subject to any regulations (Roth et al. 1994, 802). Literature See also the entries for Cytisus spp. and Sophora secundiflora. Hayman, Alison R., and David O. Gray. 1989. Hydroxynorcytisine, a quinolizidine alkaloid from Laburnum anagyroides. Phytochemistry 28 (2): 673-75. Murakoshi, Isamu, Kyoko Fukuchi, Joju Haginiwa, Shigeru Ohmiya, and Hirotaka Otomasu. 1977. N-(3-oxobutyl)cytisine: A new lupin alkaloid from Echinosophora koreensis. Phytochemistry 16:1460-6l. Plugge, P. C. 1895. Uber das Vorkommen von Cytisin in verschiedenen Papilionaceae. Archiv fur Pharmazie 233:430 ff. Plugge, P. C., and A. Rauwerda. 1896. Fortgesetzte Untersuchungen Dber das Vorkommen von Cytisin in verschiedenen Papilionaceae. Archiv fur Pharmazie 234:685 ff. Seeger, R., and H. G. Neumann. 1992. Cytisin. Deutsche Apotheker Zeitung 132:303-6.