Cytisine

Cytisine
Clinical data
Other names	Cytisine; Baptitoxine; Sophorine
License data	US DailyMed: Cytisine;
ATC code	N07BA04 (WHO) ;
Identifiers
	IUPAC name (1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,3]diazocin-8-one;
CAS Number	485-35-8;
PubChem CID	10235;
IUPHAR/BPS	5347;
DrugBank	DB09028;
ChemSpider	9818;
UNII	53S5U404NU;
ChEBI	CHEBI:4055;
ChEMBL	ChEMBL497939;
CompTox Dashboard (EPA)	DTXSID00883395 ;
ECHA InfoCard	100.006.924
Chemical and physical data
Formula	C11H14N2O
Molar mass	190.246 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	152 °C (306 °F)
Boiling point	218 °C (424 °F)
	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; Key:ANJTVLIZGCUXLD-DTWKUNHWSA-N;

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.^[1] Although widely used for smoking cessation in Eastern Europe, cytisine remains relatively unknown beyond it.^{[citation needed]} However, it has been found effective in several randomized clinical trials, including some in the United States and a large one in New Zealand,^[1] 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).^[2] It has also been used entheogenically via mescalbeans by some Native American groups, historically in the Rio Grande Valley predating even peyote.^[3]

^ ^a ^b Walker N, Howe C, Glover M, McRobbie H, Barnes J, Nosa V, et al. (December 2014). "Cytisine versus nicotine for smoking cessation". The New England Journal of Medicine. 371 (25): 2353–2362. doi:10.1056/nejmoa1407764. PMID 25517706. S2CID 13759117.
^ Thomas D, Farrell M, McRobbie H, Tutka P, Petrie D, West R, et al. (May 2019). "The effectiveness, safety and cost-effectiveness of cytisine versus varenicline for smoking cessation in an Australian population: a study protocol for a randomized controlled non-inferiority trial" (PDF). Addiction. 114 (5): 923–933. doi:10.1111/add.14541. PMID 30589984. S2CID 58621453.
^ Howard JH (1957). "The Mescal Bean Cult of the Central and Southern Plains: An Ancestor of the Peyote Cult". American Anthropologist. 59 (1): 75–87. doi:10.1525/aa.1957.59.1.02a00070. JSTOR 666531.

[CytisineVsNRTNZ-1] Walker N, Howe C, Glover M, McRobbie H, Barnes J, Nosa V, et al. (December 2014). "Cytisine versus nicotine for smoking cessation". The New England Journal of Medicine. 371 (25): 2353–2362. doi:10.1056/nejmoa1407764. PMID 25517706. S2CID 13759117.

[Thomas2019-2] Thomas D, Farrell M, McRobbie H, Tutka P, Petrie D, West R, et al. (May 2019). "The effectiveness, safety and cost-effectiveness of cytisine versus varenicline for smoking cessation in an Australian population: a study protocol for a randomized controlled non-inferiority trial" (PDF). Addiction. 114 (5): 923–933. doi:10.1111/add.14541. PMID 30589984. S2CID 58621453.

[3] Howard JH (1957). "The Mescal Bean Cult of the Central and Southern Plains: An Ancestor of the Peyote Cult". American Anthropologist. 59 (1): 75–87. doi:10.1525/aa.1957.59.1.02a00070. JSTOR 666531.

[1]

[2]

[3]