[Monoamine oxidase inhibitors. I. Synthesis of N-cyclopropyltryptamines].
The synthesis of two new N-cyclopropyltryptamines is described. By treating 5,6-dimethoxyindole with oxalyl chloride and N-benzylcyclopropylamine, N-benzyl-N-cyclopropyl-5,6-dimethoxyindole-3-glyoxalamide is obtained. The reduction of this compound by LiAlH4, gives N-benzyl-N-cyclopropyl-5,6-dimethoxytryptamine, which is hydrogenated to N-cyclopropyl-5,6-dimethoxytryptamine. Similarly N-cyclopropyl-6,7-dimethoxytryptamine is prepared. Preliminary results indicate a different specificity of the inhibitors used on mitochondrial and bovine plasma enzyme (monoamine oxidase) attributable to the position of the methoxy groups.
D008735:5-Methoxytryptamine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000818:Animals; D002417:Cattle; D055598:Chemical Phenomena; D002621:Chemistry; D008996:Monoamine Oxidase Inhibitors / Q000138:chemical synthesis*; D014363:Tryptamines / Q000138:chemical synthesis*
D008996:Monoamine Oxidase Inhibitors; D014363:Tryptamines; D008735:5-Methoxytryptamine; C028224:N-cyclopropyl-5,6-dimethoxytryptamine; C028225:N-cyclopropyl-6,7-dimethoxytryptamine
Richerche su sostanze inibitrici delle monoaminossidasi. Nota I. Sintesi di N-ciclopropiltriptamine.