Hehe well for starters -NH is a much better nucleophile than -OH, you can apparently acetylate such amines with a very benign acetylating agent as ASA. Where -OH acetylation will require more, a base to deprotonate (or for nucleophilic catalysis) and your industry standard acetylating agent.
It shouldn't be necessary, however, to acetylate. Its not hard to keep the -OH protonated, psilocin is neutral and is soluble in the appropriate organic solvent as per the literature.
i've always thought that potential H-bonding interaction had a lot to do with psilocins potency, maybe easier to bypass MAO or increase BBB permability (hiding the polarity, like you said DFZ)
Expect nothing, Receive everything.
"Experiment and extrapolation is the only means the organic chemists (humans) currrently have - in contrast to "God" (and possibly R. B. Woodward). "
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"The most beautiful thing we can experience, is the mysterious. The source of all true art and science."