Metabolism of naturally occurring propenylbenzene derivatives. II. Separation and identification of tertiary aminopropiophenones by combined gas-liquid chromatography and chemical ionization mass spectrometry.

A more simplified method of identification of the tertiary aminopropiophenones formed from various allylbenzene derivatives is reported. By use of combined gas-liquid chromatography and chemical ionization mass spectrometry, one is able to detect and verify the chemical structure of the tertiary aminopropiophenones of elemicin on nanogram quantities in the crude basic urine fraction. By use of this analytical method, it is concluded that upon oral administration of purified elemicin the rat excretes in urine the 3-N,N-dimethylamino-, the 3-piperidyl-, and the 3-pyrrolidinyl-~-(3’,4’,~‘-trimetl~oxyphenyl)-propan-r-ones. These tertiary aminopropiophenones of elemicin seem to decompose more easily than those reported for safrole and myristicin.