3928. Fagarine

Nomenclature

CAS number: 524-15-2
4,8-Dimethoxyfuro[2,3-b]quinoline; γ-fagarine; 8-methoxydictamnine.
C13H11NO3; mol wt 229.23.
C 68.11%, H 4.84%, N 6.11%, O 20.94%.

Description and references

Antiarrhythmic principle in Fagara coco (Gill.) Engl., Rutaceae. Isoln: Deulofeu et al., J. Am. Chem. Soc. 64, 2326 (1942); Briggs, Cambi, Tetrahedron 2, 256 (1958). Structure: Berinzaghi et al., J. Org. Chem. 10, 181 (1945). Synthesis: Grundon, McCorkindale, Chem. Ind. (London) 1956, 1091.

Chemical structure

Properties

Prisms from alcohol, mp 142°. uv max: 238, 332, 370 nm (log ε 4.76, 3.88, 3.89). Sol in chloroform, benzene, ether; slightly sol in water, petr ether.

Derivative

Hydrochloride.
C13H12ClNO3; mol wt 265.69.
C 58.77%, H 4.55%, Cl 13.34%, N 5.27%, O 18.07%.

Properties

Needles from chloroform + ether, mp 158-159°.