Cytisine

Cytisine, also known as baptitoxine, cytisinicline, or 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. Although widely used for smoking cessation in Eastern Europe, cytisine remains relatively unknown beyond it. However, it has been found effective in several randomized clinical trials, including some in the United States and a large one in New Zealand, and is being investigated in additional trials in the United States (being conducted by Achieve Life Sciences) and a non-inferiority trial in Australia in which it is being compared head-to-head with the smoking cessation aid varenicline (sold in the United States as Chantix). It has also been used entheogenically via mescalbeans by some Native American groups, historically in the Rio Grande Valley predating even peyote.

Cytisine
Clinical data
Other namesCytisine; Baptitoxine; Sophorine
License data
ATC code
Identifiers
  • (1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,3]diazocin-8-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.924
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
Melting point152 °C (306 °F)
Boiling point218 °C (424 °F)
SMILES
  • O=C1/C=C\C=C2/N1C[C@@H]3CNC[C@H]2C3
  • 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
  • Key:ANJTVLIZGCUXLD-DTWKUNHWSA-N
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