I'm not sure exactly if this is the right place to post this, but it is about methods, so I thought it would best go here. It could just as easily apply to other plant alkaloid extraction processes, since sugars are universally present in plants. I am happy to see this moved to the tryptamines forum, but I think that here it will attract more comments from more knowledgable chemistry folk.
SWIM recently did an extraction from a fairly large quantity of acacia obtusifolia bark, and for the second time encountered a problem with what he believes to be sugars in the sap that are extracted.
The acidic extraction was done at a pH of about 3, and when the whole solution was reduced to 500ml (from about 20L) it became a thick soupy sticky consistency, which defeated all efforts to properly filter it.
It also made defatting almost impossible, since the sugars are also amphoteric and the separation of the nonpolar solvent very innefficien and lots of residual defatting solvent ends up in the final extraction.
SWIM was thinking that maybe other SWIMs had worked with larger quantities, and could inform SWIM of the best way to eliminate this problem.
These are the ideas that SWIM has had regarding this:
The problem seems to stem from the fact that sugars are in fact miscible in water. Thus, although he expects that no significant loss of product occurs, a mixture which is more than half sugars becomes very difficult to work with.
Thus first of all, he thinks that filtration should be done on the unreduced liquid, as in this state it flows freely and would not clog the filter quite so much as the sugars which coat and thicken preventing the flow of the solution. Using progressive filtration, starting with a strainer, then through a single layer of cloth, and then multiple layers of cloth and finally through coffee filters.
The other idea that is coalescing is that it might be possible to use salting out to drive the alkaloid salts out of the solution, thus separating them from the undesirable sugars. This would be done in a fair excess, well before the solution becomes too thick, it doesn't matter much if there is an excess of salt, as this will not completely confound the extraction, it will mean that more base will be required to achieve the high pH required for extraction.
After adding an excess of salt to the solution, the solution would be cooled, and the supernatant (above the precipitate) liquid should be now safe to discard. The alkaloids will drop to the bottom along with other substances which are less soluble in the water due to the full saturation of the solution with salt. Thus they should remain in the bottom of the container when pouring it off.
The liquid at the bottom should now be relatively free of the sugars, while other substances, such as tannins and mineral salts, along with the alkaloid salts which will make the defatting step much simpler.
The technique of salting out as used in the manske extraction has been demonstrated (by me) to work with other alkaloids, namely caffeine and hypericin, so there is no reason to suspect that DMT tartrate or whatever acid ion bound to it wouldn't likewise drop to the bottom of the container.
The elimination of the sugars would make the whole process a lot simpler.
I would like to hear other chem savvy folks comments on this idea. Even in small extractions, this would reduce the amount of material very dramatically, and make defatting a hell of a lot more effective.
SWIM, of course, depleted the last of his stock of obtusifolia bark in this most recent 'disaster', though perhaps he might have *some* alkaloids left in the bark that this extraction was done with, but probably not much, and the ratio of sugars to material is probably majorly depleted compared with fresh material. He's run out of funds to continue further experiments at this point, and is also imminently about to become homeless, but he will definitely pursue this experiment.
