Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA)

Journal of Medicinal Chemistry
M A ParkerD E Nichols

Abstract

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 agents and as serotonin agonists. The 2-methyl derivative 2a and the 5-methyl derivative 2b 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.

References

Jan 1, 1991·Pharmacology, Biochemistry, and Behavior·D E NicholsR Oberlender
Feb 1, 1990·Journal of Medicinal Chemistry·D E NicholsR M Riggs
Oct 1, 1986·Journal of Psychoactive Drugs·A T Shulgin

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Citations

Oct 31, 2009·Journal of Medical Toxicology : Official Journal of the American College of Medical Toxicology·David M WoodPaul I Dargan
Mar 1, 2012·Drug Testing and Analysis·Daniel Trachsel
Mar 6, 2010·Annals of the New York Academy of Sciences·Kyle C Schmitt, Maarten E A Reith
Feb 25, 2006·Bioorganic & Medicinal Chemistry·Nuno MilhazesFernanda Borges
Dec 29, 2006·Chemistry & Biodiversity·Daniel TrachselFranz Baumberger
Jul 13, 2018·ACS Chemical Neuroscience·Lee E DunlapDavid E Olson
Apr 7, 2020·Journal of the American Chemical Society·Talia J SteimanAbigail G Doyle

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