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.
D015104:3,4-Methylenedioxyamphetamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000662:Amphetamines / Q000138:chemical synthesis*; D000700:Analgesics; D000818:Animals; D002491:Central Nervous System Agents / Q000138:chemical synthesis*; D000697:Central Nervous System Stimulants; D004285:Dogs; D006168:Guinea Pigs; D000882:Haplorhini; D006801:Humans; D066298:In Vitro Techniques; D007928:Lethal Dose 50; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D051381:Rats; D011930:Reaction Time / Q000187:drug effects; D013045:Species Specificity
D000662:Amphetamines; D000700:Analgesics; D002491:Central Nervous System Agents; D000697:Central Nervous System Stimulants; D015104:3,4-Methylenedioxyamphetamine