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Cytisine
Cytisine.svg
IUPAC name
Other names Cytisine
Baptitoxine
Sophorine
Identifiers
CAS number 485-35-8 Yes check.svgY
SMILES
InChI
Properties
Molecular formula C11H14N2O
Molar mass 190.24 g/mol
Melting point

152-153 °C

Boiling point

218 °C at 2 mmHg

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cytisine, also known as baphitoxine and sophorine, is a pyridine-like alkaloid that can be toxic in high doses. 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

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)

Uses

Cytisine is a nicotinic acetylcholine receptor agonist, and as a pharmaceutical preparation it is available for the treatment of nicotinism. The 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.

References

  1. ^ Etter JF. Cytisine for smoking cessation; a literature review and a meta-analysis. Arch Intern Med 2006;166:1553-9. PMID 16908787.
  • 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

External links


1911 encyclopedia

Up to date as of January 14, 2010

From LoveToKnow 1911

CYTISINE (Ulexin, Sophorin), C 11 H 14 N 2 O, an alkaloid discovered in 1818 by J. B. Chevreul in the seeds of laburnum (Cytisus Laburnum) and isolated by A. Husemann and W. Marme in 1865 (Zeit. f. Chemie, 1865, i.p. 161). It is also found in the seeds of furze (Ulex europaeus), Sophora tormentosa, and Euchresta horsfieldii. !It is extracted from the seeds by an After E. Ray Lankester, Ency. Brit., 9th e Cystoflagella d.

to Protozoa.

6. Noctiluca miliaris, acted upon by iodine solution, showing the protoplasm shrunk away from the structureless pellicle.

a = entrance to atrium.

7. Lateral view of Noctiluca miliaris. a, entrance to atrium.

b, atrium.

c, superficial ridge.

d, big flagellum.

e= mouth and gullet, in which is seen Krohn's oral flagellum (=the chief flagellum, or flagellum of the longitudinal groove of Dinoflagellata).

broad process of protoplasm extending from the superficial ridge c to the central protoplasm.

g, duplicature of pellicle in connexion with superficial ridge.

h, nucleus.

f, alcoholic solution of acetic acid, and forms large crystals which melt at 153° C., and are easily soluble in water, alcohol and chloroform. It is a secondary and tertiary di-acid base, and is strongly alkaline in its reaction. Hydrogen peroxide oxidizes it to oxycytisine, C11H14N202, chromic acid to an acid, C11H9N03, and potassium permanganate to oxalic acid and ammonia. It acts as a violent poison.

See further, P. C. Plugge, Arch. der Pharm. (1891), 229, p. 48 et seq.; A. Partheil, Ber. (1890), 23, p. 3201, Arch. der Pharm. (1892), 230, p. 44 8; M. Freund and A. Friedmann, Ber. (1901), 34, p. 615; and J. Herzig and H. Meyer, Monats. f. Chem. (1897), 18, p. 379


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