Preparation of a Deuterated Analog of Tetrahydropapaveroline Suitable for Use as an Internal Standard for G.C./M.S. Analysis of This Alkaloid: Retro Pictet-Spengler Condensation

Abstract

Attempts to prepare deuterated analogues of salsolinol and tetrahydropapaveroline by exchange procedures in D₂O have demonstrated that the Pictet-Spengler reaction is a reversible process. Tetrahydropapaveroline can be readily obtained from papaverine by reduction with Zn/HCl followed by demethylation in a process which can conveniently be adapted to produce a (²H₃)analogue.