3-Ethyl-1,2,3,4,5,6,8,9,9a,14-decahydro-9a-hydroxy-3,7-methanoazocino[1',2':1,2]pyrrolo[2,3-b]indol-7-ium

Two alkaloids of this name have been described in the literature. The first, discussed here, is found in Aspidosperma quebracho blanco, Gonioma kamassi and Rhazya stricta. It has been shown to exist in two interconvertible forms (a) Rhazidine base (Rhazidigenine) which forms colourless crystals, m.p. 187°C and has [α]_D - 612° (alkaline EtOH). It gives an ultraviolet spectrum showing four absorption maxima at 210, 281, 292 and 307 mJi, (b) Rhazidine salt, a quaternary base forming a crystalline chloride, m.p. 285°C (dec.); [α]_D - 40° (EtOH) which gives an ultraviolet spectrum in neutral solution (EtOH) with absorption maxima at 236 and 293 ffiJ1 and in alkaline solution (NaOH-EtOH) at 220, 283, 293 and 307 mμ

Spiteller-Friedmann et al., Monatsh., 95, 1228 (1964)
Markey, Biemann, Witkop., Tetrahedron Lett., 157 (1967)