Pithecolobine, the Alkaloid of Pithecolobiumsaman Benth. I

Pithecolobine, C 22 H 46 N 4 O 2 , has a lactam group, one primary and two secondary amino groups, and a hydroxyl group. Lithium aluminum hydride converts it into a monocyclic saturated compound, desoxypithecolobine, C 22 H 48 N 4 . Hofmann degradation of this compound gives tetramethylputrescine, trimethyl amine, a doubly unsaturated base C 16 H 31 N with a terminal methylene group, and a base C 16 H 34 N 2 . Heating with selenium yields a hydrocarbon, C 12 ;H 24–26 , with a sequence of six or more CH 2 groups. A crystalline oxygen-free compound with two nitrogens (m.p.94 °C.) is also obtained, the ultraviolet spectrum of which is almost identical with aminopyridine.