I'm a bit unclear on what exactly did and did not work. Let me attempt to summarize SWIY's experiments:
1) mescaline tartrate would not crystalize (did SWIY do this one?)
2) mescaline bitartrate would not crystalize
3) mescaline fumarate is soluble in d-limonene so crystallization was not attempted
4) mescaline citrate would not crystallize (though others report success)

These tests (except for one?) happened a while back and it is possible that there just wasn't enough mescaline there to crystallize.

Does that sound like a fair summary?

I'd like to know how likely it is that there just wasn't any mescaline in there and that we could go back to our prior (highish) probabilities that crystallization would be easy. I know SWIY had a bunch of trouble with mescaline extractions in the past (at least partly due to bunk cactus, and part due to washing the xylene with water), so if I'm understanding right, it seems like lack of mescaline is likely the reason it didn't crystallize, especially given that there is a report of mescaline tartrate crystallizing well, and several of citrate crystallizing.

If you think there's a decent chance recrystallization would work, SWIM would still like to give it a try for experimentation's sake (he can always redo a small scale A/B if it all fails). If not, SWIM will try acetone washes and then IPA washes. The only IPA SWIM could find locally was 70% so he salted it out and will dehydrate further with MgSO4- this should be good enough, right?

Thanks

Exactly, so don't be too surprised if you have success even though SWIM didn't

No...you absolutely need 99% IPA for the final wash. No other substitute will work

What is IPA?

In that case, SWIM will give it a try.

Hmm.. I had a hard time finding reliable numbers for salted out IPA, but those that I did find said it was 99%. Is it that the 1% water is necessary (and this makes it too dry - 100% IPA won't work) or that salting and adding MgSO4 cant get close enough to anhydrous? There are other stores in SWIMs are that he hasn't checked, so if the crystallization thing doesn't work out, he'll look harder.

Thanks

I weighed out 420mg of *dark* brown mescaline hydrochloride, and then weighed out 1000mg of tartaric acid and 250mg of NaOH (should produce a slight excess of sodium bitartrate even if the mescaline was pure). The acid and base were added to 2floz of hot water and then the mescaline was dissolved. This was filtered, and quite a bit of dark gunk came out.

The solution was then put in the freezer, but nothing crystallized out before it started to freeze. The solution was then poured in a glass baking dish and put in the oven at low heat to evaporate off some of the water. The oven was turned off after maybe an hour, but it wasn't checked until the next morning.

There are pretty crystals in the baking dish. There is still over half of a fluid ounce of liquid left over. I'm not sure if the crystals are sodium bitartrate or mescaline bitartrate, as the solubility of sodium bitartrate is low enough for it to have started crystallizing. I still have to separate the crystals from the solvent (scrape up and rinse with ice water?) and test the melting point.

If the mass is greater than it could be with just sodium bitartrate and the melting point != 253C (probably lower), then it's probably mescaline. I could also try crystallizing sodium bitartrate on its own to see if the crystals look similar or not. Of course, the final test is bioassay, but that isn't going to be for a while.

Any ideas?

I poured it all in a coffee filter and let the water drip through. I then rinsed it a couple times with ice water.

I dried the liquid portion in the glass baking dish in the oven, and let the filter paper dry in the air. I ended up with these beautiful gold/beige looking crystals. The catch is that there's only 105mg of them =\. Theres 1.05g of the other crap that made it through the filter (which isn't pretty at all).

Assuming this is mescaline bitartrate, it is only 1/3 as potent as mescaline HCl and I only recovered ~10% of my original sample. Either it was *extremely* impure or the rest must be in the gunky crystalline stuff.

Another possibility (seems more likely) is that mescaline bitartrate is fairly soluble, but mescaline tartrate is not, and that my careless weighing was 15mg of NaOH too much, and therefore there was some tartrate anions in solution. Then mescaline tartrate crystallized out, but the rest of the mescaline was trapped as something that wouldn't crystallize.

The report here talks about "olive" colored "mescaline tartrate". "Olive" sounds like it could be describing the same color, and his crystals clearly were not very soluble so I think we're talking about the same substance. He seemed to use an excess of tartaric acid, so I would expect him to end up with the tartrate as opposed to the bitartrate.

This all seems to point in the direction of "mescaline bitartrate doesn't crystallize well, but mescaline tartrate does".

If all goes well, it looks like this could be a method for easy extraction (no AB bs). Just boil down to small volume, add excess tartaric acid and crystallize out. The crystals came out very pretty and pure looking even though the mescaline I started with was not very pure, so hopefully even without the nonpolar step a decent purity can be obtained (and a simple recrystallization should get more pure).

Tomorrow I will add more NaOH to convert the bitartrates to tartrates and see what happens. Wish me luck!