Psychotridine, a C₅₅H₆₂N₁₀ Alkaloid From Psychotria beccarioides (Rubiaceae)

Abstract

Psychotridine, the major alkaloid from Psychotria beccarioides Wernh. has the molecular composition C₅₅H₆₂N₁₀. It has been shown to be related to hodgkinsine, and a structure (4) derived from five N_b-methyltryptamine units is proposed. Mass spectral evidence for the structure is supported by the conversion of psychotridine through a pentamethiodide into a penta-indolenine base, analogous to the tri-indolenine base derived from hodgkinsine N_b,N_b',N_b?-trimethiodide. The structure is also supported by comparison of the ¹³C N.M.R. spectra of hodgkinsine and psychotridine.