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So I'm currently to see if I can make a bit of 5-HO-DMT from 5-MeO-DMT, since this are legal where I live.... Believe it or not, but 5-MeO-DMT is easier to come by then serotonin in these parts.

But anyway, I heated the 5-MeO for a few hours in aqueous HBr to try to snip the methyl off. (I briefly boiled off any MeBr and MeOH that might have formed).
Then I did what everyone here loves to do most and made it basic with NaOH. I extracted the (hopefully) 5-HO-DMT freebase with ethyl acetate a few times, and finally gave with another wash wth slightly basic water.

One issue here is that there are a LOT of impurities forming, which is probably mostly NaBr. Now, in principle this shouldn't be too much of an issue since salts should stay in the aqueous phase, (but for some reason I still think some got into the ethyl acetate somehow)...

But now for the purification: I tried to recrystallize the 5-HO-DMT by adding some acetone to the ethyl acetate and put it in the freezer.
The next day there was indeed some `ice' in there (not the solvents) but when I took it out, the volume looked way too big to be just the 5-HO-DMT, so it was probably a mixture of the alkoyd and left over NaBr.

The question/conundrum :

bDoes anyone know a good solvent for recrystallizing 5-HO-DMT? I think one problem is that even though we're dealing with the freebase here, which should not be soluble in polar solvents, the OH group probably does make it somewhat polar though...

I guess as a last resort I could turn it into the hydrochloride salt, so that it's totally polar and then try to crystalize it from something that will dissolve it at room temperature but not in the fridge?? Again any insights would be greatly appreciated!

You can find solvents for purification here.

Just go with Xylene. This will keep unreacted 5-MeO dissolved even in freezer.

But actually are you sure that you can cleave off 5-MeO to Bufotenin?

This ether should not just vanish by NaOH.

Scifinder tells to cleave off methylated phenols by using

A) platinum catalyzed Hydrogenation/Reduction = Pt/H2

B) ether cleavage by using Borontribromide = BBr3

First way is possibly way too much labour and 2nd way involves a quite toxic chemical. So I think its a really unfeasible route. Therefore I highly doubt that simple NaOH would do the job.

In case that it didnt work this means you would also have no precipitation when using a minimal amount of Xylene to dissolve it. You could do a first try. If solution stays clear you only had 5-MeO.

HBr was used, which should probably do the trick (The unstated third/fourth option, HI, does for all sorts of aromatic methyl ethers).