Defatting: Why not do it first?

[Cvank Svanulson]

Hey all,

Every tek I've come across on the net for alkaloid extraction that contains a defatting step usually has this at a later stage in the process (after alkaloids have been separated from the plant material). I was thinking it would make sense to do this before the A/B procedure using an acidified non-polar solvent. If I'm not mistaken, soaking the plant material in something like chloroform acidified with glacial acetic acid should strip out the fats and other non-polar stuff, leaving the alkaloids behind in the plant material (they should be positively charged under the acidic conditions and therefore insoluble in the apolar solvent). Then of course one could strain out the stuff and proceed to A/B extract the now defatted plant material.

Has anyone ever done this step first in their extractions? If not, I would like to know if there is reason not to. I know a lot about chemistry and this seems like it should theoretically work.

 

[endlessness]

Yes you can do defat on plant material, but no definitely dont use chloroform with acetic acid. DMT and DMT n-oxide acetates are somewhat soluble in chloroform, so they will stay in both layers, the organic and the acqueous (Banerjee & Ghosal 1969 ).

Im not sure if the alkaloids in their natural salt form (tannate for mimosa? or other possibilities... ?) are soluble in chloroform (or other solvents), so I dont know if un-acidified chloroform will work well or not. Most other non polars should work.

Also notice that while n-oxide is not really soluble in naphtha/pet ether, it IS soluble in it when there are oils present (also banerjee & ghosal 1969) since the oils dissolve in pet ether and will help dissolving n-oxide. So if the plant material you are using potentially has n-oxides, the safest bet to get full yield would be to reduce it using zinc dust and acetic acid, and later pull normally as you would with DMT.

Now back to defatting issue, why are you defatting at all? Defatting was an old process that was used before people knew "tricks" around it. The main "trick" that was developed is fumarate precipitation. Xylene+FASA or limonene + FASI will eliminate the need for defat since the alkaloids will precipitate from your solvent directly, while leaving most fats and impurities behind. Not only its a very nice process as the alkaloids crystallize, but it also saves up on solvent, you dont have to throw away all this defatting solvent.

To reuse FASA or FASI-filled solvent, wash several times with water to remove IPA/acetone.

Also remember to let the FASA/FASI solvent to crystallize for a couple of weeks or more, as it takes a while for it to fully crystallize. Add FASI/FASA to your solvent till it stops cloudying more, wait 2-3 weeks, filter/scrape, add more FASI/FASA, let it stand for a few more days and see if more crystalizes.

Good luck! (and welcome to the forum btw! Hope you write an intro essay and stay with us )

 

[Cvank Svanulson]

Thanks for the tip. That is a great extraction technique for tryptamine alkaloids.
I was thinking about defatting first as a general procedure for any alkaloid, particularly mescaline from cacti, which are notorious for forming emulsions. What I had in mind was to first suspend the biomass in non-polar solvent, decant/filter, and then process the plant material from there. That way, the step where the free base is transferred to non-polar solvent should go a lot smoother. My only fear is losing alkaloids to the defatting solvent (I'm not sure about whether or not some alkaloids are naturally in their free base form in the plant, or is it always going to be a salt?).

 

[endlessness]

Cacti emulsions? Just raise the pH / add pure NaCl / vibrate, that should eliminate emulsions quickly. You can also do FASI with cactus (I would guess FASA too).

Is your only problem emulsions?

Im not sure about defatting cactus, I would guess the alkaloids are in salt form too because they are readily soluble in non-acidified water, meaning the cact must be acidic and therefore it should all be in salt form, so the right solvent choice could potentially work. Are you set on doing the defatting or would you try fumarate precipitation or other techniques?

 

[Cvank Svanulson]

Okay so after looking at the various posts on FASA/FASI methods, it seems that they work best with DMT and not with mescaline. It looks like instead of fumaric acid, one should use HCl or H2SO4 instead.

SWIM plans on doing the following:

1) Basify cactus material, and do xylene pull.

2) Strip the xylene, and re-dissolve gunk in acetone (freebase should be soluble right?)

3) Salt out mescaline by adding conc. HCl or H2SO4 (mesc-HCl should not be soluble).

Feel free to point out any glaring flaws in my idea.