Cytisine

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Cytisine
IUPAC name (1R,5S)-1,2,3,4,5,6-hexahydro-
1,5-methano-8H-pyrido[1,2a][1,5]
diazocin-8-one
Other names Cytisine
Baptitoxine
Sophorine
Identifiers
CAS number [485-35-8]
SMILES O=c1cccc2C3CNCC(C3)Cn21
InChI 1/C11H14N2O/c14-
11-3-1-2-10-9-4-8
(5-12-6-9)7-13(10)
11/h1-3,8-9,12H,4-7H2
Properties
Molecular formula C11H14N2O
Molar mass 190.24 g/mol
Melting point

152-153 °C
Boiling point

218 °C at 2 mmHg
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Cytisine is a toxic pyridine-like alkaloid. Pharmacologically it exhibits similar effects to nicotine due to structural similarity of the two molecules. In large doses it can interfere with respiration and become fatal.

Contents

[edit] Sources

Plants that contain the alkaloid in various concentrations include those from several genera of the Faboideae subfamily, including Laburnum, Anagyris, Thermopsis, Cytisus, Genista and Sophora. Also present in Gymnocladus of the Caesalpinioideae subfamily.

Māmane (Sophora chrysophylla) can contain amounts of cytisine that are lethal to most animals. The palila (a bird) and Uresiphita polygonalis virescens as well as Cydia species (moths), and possibly sheep and goats are not affected by the toxin for various reasons and utilize māmane, or parts thereof, as food. U. p. virescens caterpillars are possibly able to sequester the cytisine to give themselves protection from getting eaten; they have aposematic coloration which would warn off potential predators.(Banko et al. 2002)

[edit] Uses

Cytisine is a nicotinic acetylcholine receptor agonist, and as a pharmaceutical preparation it is available for the treatment of nicotinism. Cytisine derivative varenicline was approved in 2006 as a smoking cessation drug. A 2006 literature review concludes that while trials performed with cytisine itself are mostly of poor quality, there is some evidence that cytisine may be prescribed to aid in smoking cessation.[1]

Plants containing cytisine, including the Common Broom and Mescalbean have also been used recreationally. Positive effects are reported to include a mild intoxication and heightened awareness of color. However this practice is not recommended since negative side-effects can include nausea, vomiting, convulsions, heart pain, headache and in larger doses even death via respiratory failure.

[edit] References

  • Banko, P.; Cipollini, M.L.; Breton, G.; Paulk, E.; Wink, M. & Izhaki, I. (2002): Seed chemistry of Sophora chrysophylla (Mamane) in relation to the diet of the specialist seed predator Loxioides bailleui (Palila) in Hawai'i. Journal of Chemical Ecology 28(7): 1393-1410.doi:10.1023/A:1016248502927 PDF fulltext
  1. ^ Etter JF. Cytisine for smoking cessation; a literature review and a meta-analysis. Arch Intern Med 2006;166:1553-9. PMID 16908787.

[edit] External links