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IANAdrugologist but that rule is about bioactivity rather then psychoactivity. Open to correction though.

you're correct. it doesn't help a lot with predicting psychedelic activity other than to act as a negative filter for unlikely compounds.

Yes, it's just one piece of the puzzle. The op might also be interested in David E Nichols' research into structure-activity relationships of psychedelics. See: https://web.archive.org/web/20080704190159/http://www.heffte...