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Thoughts on the Hypotheticals...
It seems to me that your first question and your third question are really the same. I have quite a few responses to this entire topic that perhaps shed some light on why it seems more comfortable, safe, right to limit psychedelic drug use to "the narrow context of 'medical' conditions".
It's very interesting that descriptions of trips on these drugs are largely positive and emphasize interconnectedness, unity, and empathy. This line of reasoning really resonates with me that perhaps this kind of drug use should not be limited to the medical box. However... the unpredictability of trips, and the harm that could result from them, makes me wary of extending legalizing them to recreational use. Someone during our discussion brought up the example of a busdriver tripping on these drugs to highlight the possibility of unintentional harm being caused as a result of a bad (or even a good!) trip. This line of reasoning is very similar to utilitarian philosophy, as in "your right to swing your fist ends at my nose". A different phrasing that suits this example better might be that a busdriver's right to a positive and beneficial trip ends when my child's wellbeing is put in jeapordy. The problem with this reasoning is that, of course, since so much data regarding the unpredictability of trips is anecdotal, we really don't know the frequency of bad trips vs. good trips. Couldn't medical research help here? Couldn't medical reserach be seen as a stepping stone to gathering more data to assess whether further legalization is appropriate?
I think this strong reaction that I have to this possible, though perhaps unlikely scenario sheds light on a catch 22 many people have about psychopharmacology in general. There have been several international headlining news regarding unpredictable behavior as a result of drug use. I'm thinking here of mass shooting tragedies in the US attributed to the dramatic effects of taking drugs or rapidly coming off a drug regimine. Why am I so wary about the psychodelics and not as wary about SSRIs, if they can have equally devastating potential consequences? It seems to me that if we're criticizing the psychodelics, our criticism must extend to reevaluate the drugs currently in circulation...
This was all a very roundabout way of saying, I don't think that limiting a discussion about psychedelics to "the narrow context of 'medical' conditions" is necessarily a bad thing at all. I think, rather, it could prove to be a way of creating cultural change (ex: introducing the public to a previously stigmatized group of chemicals) and more importantly (!) making a more informed policy choices regarding the legalization of this class of drugs.