Basic information Description Biological Functions References Safety Related Supplier
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Basic information Description Biological Functions References Safety Related Supplier
CYTISINE Basic information
CYTISINE Chemical Properties
  • Melting point:154-156 °C(lit.)
  • alpha D17 -120°
  • Boiling point:218 °C2 mm Hg(lit.)
  • Density 1.0815 (rough estimate)
  • refractive index 1.5700 (estimate)
  • storage temp. Store at RT
  • solubility 439g/l
  • pka6.11, 13.08(at 25℃)
  • form powder
  • color light yellow
  • optical activity[α]/D -108±3°, c = 1% in ethanol
  • Water Solubility 439g/L(16 ºC)
  • Merck 14,2789
  • CAS DataBase Reference485-35-8
  • NIST Chemistry ReferenceCytisine(485-35-8)
  • EPA Substance Registry SystemCytisine (485-35-8)
Safety Information
  • Hazard Codes T
  • Risk Statements 25-36/37/38
  • Safety Statements 26-28-36/37-45
  • RIDADR UN 2811 6.1/PG 3
  • WGK Germany 3
  • RTECS HA4025000
  • HazardClass 6.1(b)
  • PackingGroup III
  • HS Code 29399990
  • Hazardous Substances Data485-35-8(Hazardous Substances Data)
  • ToxicityLD50 in mice (mg/kg): 1.73 i.v.; 9.4 i.p.; 101 orally (Barlow, McLeod)
CYTISINE Usage And Synthesis
  • DescriptionCytisine (also known as baptitoxine and sophorine) is a kind of naturally occurring alkaloid that can be found in several plant genera including Laburnum and Cytisus in the family Fabaceae. It has been shown that it is effective in the smoking cessation treatment. It is a low efficacy partial agonist of alpha4-beta2 nicotinic acetylcholine receptors, which is the central target of the nicotine that facilitates addiction. Cytisine is capable of reducing the effect of nicotine on dopamine release on the mesolimbic system as well as attenuating the nicotine withdrawal symptoms. Cytisine is also a useful reagent for organic chemistry such as being used for the manufacture of sparteine surrogate.
  • Biological FunctionsCytisine has a physiological action similar to that of nicotine. Poisoning in Europe is generally from laburnum trees (Laburnum anagyroides, Leguminosae), while, in the tropics and America, Sophora species (Leguminosae) are often the cause. The alkaloid occurs in all parts of laburnum, but is most concentrated in the seeds, which can be mistaken for peas by children. Cytisine does not always affect cattle, but this compound can be excreted in milk and so poison children.
  • References
  • Chemical PropertiesOff-White to Tan Crystalline Solid
  • Usesantiinflammatory, respiratory stimulant
  • UsesToxic priniciple in seed of Laburnum anagyroides and other Leguminosae. A neuronal nicotinic acetylcholine agonist
  • UsesCytisine occurs in the seeds of Cytisus labur num L. and other Leguminosae.
  • DefinitionChEBI: An organic heterotricyclic compound that is the toxic principle in Laburnum seeds and is found in many members of the Fabaceae (legume, pea or bean) family. An acetylcholine agonist, it is widely used throughout Eastern Europe as n aid to giving up smoking.
  • Health HazardCytisine is highly toxic to humans and ani mals. Ingestions may cause nausea, vomiting,and convulsions. Death may occur from respiratory failure
    LD50 value, oral (rats): 101 mg/kg.
  • Biological ActivityA potent, selective agonist at neuronal nicotinic receptors. Acts as a partial agonist at β 2-containing nicotinic receptors.
  • Purification MethodsCrystallise cytisine from acetone and sublime it in a vacuum. Its solubilities are: 77% (H2O), 7.7% (Me2CO), 28.6% (EtOH), 3.3% (*C6H6), 50% (CHCl3) but it is insoluble in pet ether. The tartrate has m 206-207o [] D +45.9o, the N-tosylate has m 206-207o, and the N-acetate has m 208o. [Bohlmann et al. Angew Chem 67 708 1955, van Tamelen & Baran J Am Chem Soc 77 4944 1955, Isolation: Ing J Chem Soc 2200 1931, Govindachari et al. J Chem Soc 3839 1957, Abs config: Okuda et al. Chem Ind (London) 1751 1961, Beilstein 24 H 134, 24 I 244, 24 II 70, 24 III/IV 321.] TOXIC.
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