GAS-CHROMATOGRAPHIC MASS-SPECTROMETRIC IDENTIFICATION OF CHIRAL DERIVATIVES OF THE ALKALOIDS OF KHAT

The major alkaloids of the plant khat, Catha edulis, were conclusively identified by derivatization with -alpha-methoxy-alpha-(trifluorometh yl)phenylacetic acid. The acid was first reacted with dicyclohexyldica rbodiimide to give in situ the anhydride. The resulting amides formed from reaction with the anhydride were separated by gas chromatography. Separation characteristics of the derivatives of the alkaloids with o ther chiral acids and an anhydride are also given. Analysis of samples seized in Canada indicated large amounts of the enantiomer of cathino ne, the alkaloid chiefly responsible for the activity of the plant. In some samples almost racemic mixtures of the two isomers were detected . These results indicate that racemization of the naturally occurring cathinone in the plant is an important process.