Evidence for the Biogenic Formation of Amphetamine Derivatives from Components of Nutmeg

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Abstract
Myristicin and elemicin are phenylallyl derivatives present in nutmeg. The similarity of their chemical structure to that of mescaline or certain amphetamine derivatives has led to the assumption that the psychotropic effect of nutmeg in man is due to amphetamine derivatives endogenously produced from these phenylallyl precursors by bio-transformation. In our present study we investigated the metabolism of myristicin by rat liver, using the isolated perfused liver or incubation of liver homogenate. We have experimentally proved for the first time that rat liver is capable of converting myristicin into 3-methoxy-4,5-methylenedioxyamphetamine (MMDA). Identification of MMDA was achieved by two-dimensional thin-layer chromatography of the dansylated amine and further by mass spectroscopy.

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