Previously unreported indoles having hexyl (2), decyl (3), octadecyl (4), and cholestanylacetoxy (5) groups attached to nitrogen have been prepared. A-Methylindole (1) and 2 did not form aggregates detectable by laser light scattering but compounds 3-5 did so. Formation of vesicles was confirmed by size-exclusion chromatography, dye entrapment, and freeze-fracture electron microscopy. The surprising ability of indole to serve as a head group in single-chain, amphiphilic molecules is discussed relative to the indole residue of tryptophan and its role in the anchoring of membrane proteins.

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