cas 82801-81-8, 3,4-Methylenedioxy-N-ethylamphetamine

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Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine)
The known central nervous system activity of 3,4-methylenedioxyphenylisopropylamine and its N-methyl homolog prompted the synthesis of a series of analogs with substituents on the nitrogen atom. Most of these analogs (R = alkyl, alkenyl, hydroxy, alkoxy, and alkoxyalkyl) were prepared by the reductive alkylation of 3,4-methylenedioxyphenylacetone with the appropriate amine and sodium cyanoborohydride. Hindered isomers were synthesized indirectly. Measurements of their pharmacological activity in several animal assays and in human subjects indicated that the central activity decreased with the increasing bulk of the N-substituent.
Braun,Shulgin,Braun
p. 192 - 195
(2007/10/02)

Research on the central activity and analgesia of N-substituted analogs of the amphetamine derivative 3,4-methylenedioxyphenylisopropylamine
N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (MDA) were tested ror analgesic potency and influence on motor activity in mice following potency and influence on motor activity in mice following oral administration. These compounds also were tested for thei psychotomimetic potency in man. Unsubstituted MDA and its monoalkyl-homologs with a low number of C-atoms (N-methyl-, N-methyl-, N-ethyl-MDA) showed both enhancement of motor-activity in mice and psychotomimetic effects in man. MDA and N-methyl-MDA also showed an analgesic effec wthich was enhanced by the inclusion of a weakly labis group (N-mallyl, N-hydroxyethyl). These latter two compounds, however, did not influence motor-activity, which makes them more recommendable as possible analgesic compounds. Structural parallels between these compounds, morphine, endorphins and enkephalins, may explain their similar spectrum of pharmacological effects.
Braun,Shulgin,Braun
p. 825 - 830
(2007/10/02)