Cytisine

Not to be confused with cytosine, cysteine, or cystine.

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 Y
PubChem	10235
ChemSpider	9818 Y
UNII	53S5U404NU Y
ChEMBL	CHEMBL497939 Y
Jmol-3D images	Image 1
SMILES O=C1/C=C\C=C2/N1C[C@@H]3CNC[C@H]2C3
InChI InChI=1S/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/t8-,9+/m0/s1 Y Key: ANJTVLIZGCUXLD-DTWKUNHWSA-N Y 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/t8-,9+/m0/s1 Key: ANJTVLIZGCUXLD-DTWKUNHWBR
Properties
Molecular formula	C11H14N2O
Molar mass	190.24 g/mol
Melting point	152-153 °C
Boiling point	218 °C at 2 mmHg
Y (verify) (what is: Y/N?) 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. In medical use, it improves the rate of smoking cessation. It is less effective but much cheaper (≥$6 for a course of treatment) than similar products. Its structure is similar to nicotine and has similar pharmacological effects. In large doses, it can interfere with breathing and cause death.

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. It is also present in Gymnocladus of the Caesalpinioideae subfamily.

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 (moths), and possibly sheep and goats are not affected by the toxin for various reasons, and use 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.

Uses

Cytisine is a nicotinic acetylcholine receptor agonist, and as a pharmaceutical preparation, it is available for the treatment of tobacco smoking. It is extracted from the seeds of Cytisus laborinum L. (Golden Rain acacia) and has been available in former socialist economy (FSE) countries for more than 40 years as an aid to smoking cessation under the brand name Tabex produced by the Bulgarian pharmaceutical company Sopharma AD. It was first marketed in Bulgaria in 1964 and then became widely available in FSE countries. The cytisine derivative varenicline was approved in 2006 as a smoking cessation drug.

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.

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.

External links

• Shaman Australis Cytisine pharmacology and information on substance availability in various plants.
• Erowid Library: Golden Guide Hallucinogenic Plants by Richard Evans Schultes More on the dangerous effects of cytisine on health and respiration.
• The Vaults of Erowid : Legal Highs by Adam Gottlieb Information on recreational use.
• Cytisine Is Cheap And Effective In Helping Smokers Quit Information on treatment of tobacco smoking
• Tabex official website