ANALOGUES OF PSILOCIN AND LYSERGIC ACID DIETHYLAMIDE I. CHLORO, NITRO, AND AMINO DERIVATIVES OF3-SUBSTITUTED INDOLES

A number of indole derivatives structurally related to either psilocin or lysergic acid diethylamide (LSD) were synthesized. The following structural analogues of psilocin are reported: 4-chloro-3-dimethylaminoethylindole, 4-nitro-3-dimethylaminoethylindole, 4-nitro-3-aminoethylindole, 4-amino-3-dimethylaminoethylindole, and 4-amino-3-aminoethylindole. Compounds structurally related to LSD that were synthesized are: 3-[β-carboxyethylaminoethyl]-4-nitroindole and 4-nitro-3-[N-methyl-N-(N′,N′-diethylcarboxamidoethy-aminoethyl]indole. Several 3,5- and 3,6-disubstituted indoles are also reported.