GAS-CHROMATOGRAPHIC AND MASS-SPECTROMETRIC ANALYSIS OF N-METHYL-1-ARYL-2-PROPANAMINES SYNTHESIZED FROM THE SUBSTITUTED ALLYLBENZENES PRESENT IN SASSAFRAS OIL

One method used for the synthesis of the illicit drug N-methyl-1-(3,4-methylenedioxyphenyl)-2-propanamine (methylenedioxymethamphetamine, MDMA) involves the treatment of safrole with HBr to form the intermediate 2-bromosafrole, followed by bromide displacement with methylamine. The starting material required for this synthesis, safrole, may be obtained from sassafras oil which is isolated from the roots of the sassafras plant. In addition to safrole, sassafras oil contains other allylbenzenes such as eugenol and 4-allyl-1,2-dimethoxybenzene. Gas chromatography-mass spectrometric (GC-MS) studies show that these allylbenzenes may also be brominated and undergo amine displacement to yield the corresponding N-methyl-1-aryl-2-propanamines. These studies also show that the regioisomeric 3-bromosafrole intermediate and 3-propanamine are not formed during this synthesis. Furthermore, the isomeric allylbenzenes isosafrole and isoeugenol that are generated in these reactions do not form stable bromo products and therefore no N-methyl-1-aryl-1-propanamine products are produced during the course of the bromination and amine displacement reactions.