Cytisine

Title: Cytisine
CAS Registry Number: 485-35-8
CAS Name: (1R)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido-[1,2-a][1,5]diazocin-8-one
Additional Names: baptitoxine; sophorine; ulexine
Trademarks: Cytiton (USSR)
Molecular Formula: C11H14N2O
Molecular Weight: 190.24
Percent Composition: C 69.45%, H 7.42%, N 14.73%, O 8.41%
Literature References: Toxic principle in seed of Laburnum anagyroides Medik. and other Leguminosae. Extraction: Ing, J. Chem. Soc. 1931, 2200; Späth, Galinovsky, Ber. 65, 1526 (1932); 66, 1338 (1933); Lecoq, Bull. Soc. Chim. Fr. 10, 153 (1943). Structure: Ing, J. Chem. Soc. 1932, 2778. Synthesis: Bohlmann et al., Angew. Chem. 67, 708 (1955); Van Tamelen, Baran, J. Am. Chem. Soc. 77, 4944 (1955). Absolute configuration: Okuda et al., Chem. Ind. (London) 1961, 1751. Pharmacological properties: R. B. Barlow, L. J. McLeod, Br. J. Pharmacol. 35, 161 (1969).
Properties: Orthorhombic prisms from acetone, mp 152-153°. Sublimes. bp2 218°. [a]D17 -120°. pK1 6.11; pK2 13.08. Sol in 1.3 parts water, 13 parts acetone, 1.3 parts methanol, 3.5 parts alcohol, 30 parts benzene, 10 parts ethyl acetate, 2.0 parts chloroform. Practically insol in petr ether. LD50 in mice (mg/kg): 1.73 i.v.; 9.4 i.p.; 101 orally (Barlow, McLeod).
Melting point: mp 152-153°
Boiling point: bp2 218°
pKa: pK1 6.11; pK2 13.08
Optical Rotation: [a]D17 -120°
Toxicity data: LD50 in mice (mg/kg): 1.73 i.v.; 9.4 i.p.; 101 orally (Barlow, McLeod)
Derivative Type: Hydrochloride
Molecular Formula: C11H14N2O.HCl
Molecular Weight: 226.70
Percent Composition: C 58.28%, H 6.67%, N 12.36%, O 7.06%, Cl 15.64%
Properties: Deliquescent crystals, sol in water and alcohol. pH of 0.1 molar aq soln 4.3.
Derivative Type: Nitrate monohydrate
Molecular Formula: C11H14N2O.HNO3.H2O
Molecular Weight: 271.27
Percent Composition: C 48.70%, H 6.32%, N 15.49%, O 29.49%
Properties: Needles or leaflets, [a]D -81.5°. Sol in water, slightly sol in alcohol. Practically insol in ether.
Optical Rotation: [a]D -81.5°
Cytochalasins Cytochrome c Cytochromes P450 Cytohemin Cytolipin H

Cytisine
(-)-Cytisine.svg
Identifiers
CAS number 485-35-8 YesY
PubChem 10235
ChemSpider 9818 YesY
UNII 53S5U404NU YesY
ChEBI CHEBI:4055 N
ChEMBL CHEMBL497939 YesY
Jmol-3D images Image 1
Properties
Molecular formula C11H14N2O
Molar mass 190.24 g/mol
Melting point 152-153 °C
Boiling point 218 °C at 2 mmHg
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cytisine, also known as baptitoxine and sophorine, is a toxic alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. Despite its toxicity (LD50 i.v., in mice ~2 mg/kg),[1] it has been used medically to help with smoking cessation: it is less effective but much cheaper than similar products. Its molecular structure has some similarity to that of nicotine and it has similar pharmacological effects. Excessive doses can interfere with breathing and cause death.