Cytisine

Cytisine

Names
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
3D model (Jmol)	Interactive image
ChEBI	CHEBI:4055 N
ChEMBL	ChEMBL497939 Y
ChemSpider	9818 Y
ECHA InfoCard	100.006.924
IUPHAR/BPS	5347
PubChem	10235
UNII	53S5U404NU Y
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
SMILES O=C1/C=C\C=C2/N1C[C@@H]3CNC[C@H]2C3
Properties
Chemical formula	C11H14N2O
Molar mass	190.24 g/mol
Melting point	152 to 153 °C (306 to 307 °F; 425 to 426 K)
Boiling point	218 °C (424 °F; 491 K) at 2 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Cytisine, also known as baptitoxine and sophorine, is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. It has been used medically to help with smoking cessation. Its molecular structure has some similarity to that of nicotine and it has similar pharmacological effects. Like varenicline, cytisine is a partial agonist of nicotinic acetylcholine receptors (nAChRs). Cytisine has a short half-life of 4.8 hours, and is rapidly eliminated from the body. The use of cytisine for smoking cessation remains relatively unknown outside Eastern Europe.

Plant species that contain cytisine are found in several genera of the Faboideae subfamily of the Fabaceae family, including Laburnum, Anagyris, Thermopsis, Cytisus, Genista, Retama and Sophora. Cytisine is also present in Gymnocladus of the Caesalpinioideae subfamily.

As a pharmaceutical preparation called Tabex or Desmoxan, cytisine has been used in Eastern Europe available for the treatment of tobacco smoking. Cytisine has some structural and pharmacological similarities to the smoking cessation drug varenicline.

Cytisine is an acetylcholine agonist, and has strong binding affinity for the nicotinic acetylcholine receptor. 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.