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A number of tetrahydro‐β‐carbolines were prepared with oxygen substituents at C‐5. This class of compounds represents a hybrid between two naturally occurring groups of hallucinogenic molecules, the 4‐hydroxytryptamines and the 6‐ and 7‐oxygenated β‐carbolines.

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The synthesis of four dialkyl and three eyeloalkyl analogs of psilocin (4, R ‐ CH3), a hallucinogenic principle found in certain fungi, is described. The synthetic route involves four transformations starting with 6,7‐dihydroindol‐4(5H)one: (1).