Analogs of alpha-Methylphenethylamine (Amphetamine). I. Synthesis and Pharmacological Activity of Some Methoxy and/or Methyl Analogs.Ho, McIsaac, An, Tansey, Walker, Englert, Noel
Journal of Medicinal Chemistry 13,
1970, 26-30.
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Abstract:
A series of amphetamine derivatives substituted on the benzene ring with MeO and/or Me groups was synthesized. The pharmacological activity of these compounds was evaluated for toxicity, effects on barbiturate sleeping time, and ability to disrupt mouse behavior. Those which were active in behavioral disruption included 1-(2,5-dimethoxy-4-methylphenyl)-, 1-(2,4,5-trimethoxyphenyl)-, 1-(2,4-dimethoxy-3-methylphenyl)-, and 1-(3,4-methylenedioxyphenyl)-2-aminopropanes. In addition, 1-(3-methoxy-4-methylphenyl)-2-amino-propane, structurally resembling 1-(2,5)-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), was found to be just as active and long lasting as DOM. The amphetamine derivatives either diminished or prolonged the barbiturate sleeping time. 1-(3,4-Methylenedioxyphenyl)-2-aminopropane and DOM were equally effective in decreasing the sleeping time, while 1-(2,4,6-trimethylphenyl)- and 1-(3,5-dimethyl-4-hydroxyphenyl)-2-amino-propanes were the most active in the potentiation of the sleeping time.Besides the well known ones featuring also:2-MeO-4-Me-amphetamine
3-MeO-4-Me-amphetamine (MMA)
3,5-diMeO-amphetamine
2,3-diMeO-amphetamine
2,4-diMeO-3-Me-amphetamine
3,5-diMe-4-MeO-amphetamine
3,5-Me-4-OH-amphetamine
2,4,6-triMe-amphetamine