For the chemists out there, how difficult would it be to convert n,n-dmt to 5-meo-dmt? What would the chemical protocol look like?

eH

It wouldn't be very easy. It would require at least three steps.

1. bromination of the 5 position (bromine is no fun to work with lacking a fume hood)
2. swap out the bromine with a hydroxyl group
3. and then finally methylate the hydroxyl group (this step involves the use of very toxic chemicals that sister won't even go into here)

BUT, this type of synthetic work is well beyond the scope of what should be discussed on this board so Sister will leave it at that. You might ask the same question at places like Science Maddness or the Vespiary where such discussions are encouraged.

Bromination will hardly hit the 5 position to my understanding. And an Ullmann methoxylation would be more practical/safe than hydroxylation via SN2 + methylation, if the original reaction even panned out in any feasible yield. As Dr. Sister has said we don't discuss this kind of chemistry on the board unless it is 'safe'.

However here are some idea's to play with. In synthetic chemistry a lot of the time the reactant of choice to a desired product is not closely related or obvious. For example DMT will not undergo a selective E.A.S. reaction to hit the 5 position so it is not a good choice(as I said above). Typically 5 & 4 substitutions on indole are made before indole formation.

Bromine(Br2) can be made safely in small quantities without any elaborate set-up or chemicals but, it is toxic and corrosive. Drying of bromine must be done with the utmost of care(Cold H2SO4 will sequester moisture but also generates heat). Handling it would require a fair amount of care and should only be done in a fume hood or outside with a way to have air-flow going away from an experimenter. It must be stored cautiously and adequately it has a tendency to find it's way out of containers.

An interesting idea however would be to look at bufotenine. After the proton on the hydroxyl is stripped of course(with a base). I speculate a 'safe' easily prepared methylating agent for phenols such as methyl oxalate would do the trick at higher temperatures and under inert atmosphere(prevent oxidation of the amine and phenolate as well as carboxylation). In theory it would avoid alkylating the amine forming the nearly worthless quaternary ammonium salt, and would be relativistically safe. Workup would be easy. However, no chemistry is safe unless one knows what they are doing and how to handle when things go wrong. There are also no guarantees that this would work. Of course one would only tempt this with a proper license or in a country where it is legal to do so.

This might be better suited for advanced enhanced chemistry so long as the scope stays towards safety? Maybe a mod should decide.