2677. Cuscohygrine
Nomenclature
CAS number: 454-14-8
1,3-Bis(1-methyl-2-pyrrolidinyl)-2-propanone; cuskhygrine; bellaradine. C13H24N2O; mol wt 224.34.
C 69.60%, H 10.78%, N 12.49%, O 7.13%.
Description and references
In coca leaves of various origin. Found in crude hygrine. Readily converted to hygrine by acids and bases. Isoln: Liebermann, Ber. 22, 679 (1898); Liebermann, Cybulski, ibid. 28, 578 (1895). Identity with bellaradine: Steinegger, Phokas, Pharm. Acta Helv. 30, 441 (1955). Structure: Hess, Fink, Ber. 53, 794 (1920); Sohl, Shriner, J. Am. Chem. Soc. 55, 3828 (1933); Rapoport, Jorgensen, J. Org. Chem. 14, 664 (1949). Synthesis: Sp"ath, Tuppy, Monatsh. Chem. 79, 119 (1948); Galinovsky et al., ibid. 82, 551 (1951). Enzymatic synthesis: Tuppy, Faltaous, ibid. 91, 167 (1960). Stereochemistry: Galinovsky, Zuber, ibid. 84, 798 (1953). Biosynthesis: E. Leete, Chem. Commun. 1980, 1170.
Properties
Oily liquid, bp23 169-170°; bp14 152°; bp2 118-125°. d420 0.9733. nD20 1.4832. Miscible with water. Sol in alcohol, ether, benzene.Derivative
Hemiheptahydrate.Properties
Needles, mp 40°.Derivative
Hydrobromide.C13H24N2O.2HBr; mol wt 386.17.
C 40.43%, H 6.79%, N 7.25%, O 4.14%, Br 41.38%.