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"Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amph

"Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amph

  1. Terrapinzflyer
    Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE (March 1998)
    Journal of Medicinal Chemistry 41 (6): 1001–5. doi:10.1021/jm9705925. PMID 9526575


    The three isomeric ring-methylated derivatives of the well-known hallucinogen and entactogen MDA (1a) were synthesized and evaluated for pharmacological activity as monoamine-releasing agentsandasserotoninagonists. The2-methylderivative2aandthe5-methylderivative2b were found to be more potent and more selective than the parent compound in inhibiting [3H]- serotonin accumulation in rat brain synaptosomal preparations. Their activity in vivo was confirmed in rats trained to discriminate serotonin-releasing agents and hallucinogens from saline. The results indicate that compounds 2a,b are among the most potent 5-HT-releasing compounds known and show promise as lead compounds in the search for antidepressant drugs that release serotonin rather than inhibit its uptake.