Are we sure the activated carbon would successfully bind the oils, and not the DMT?

one way to find out...put some dmt salt in water and then run it through a carbon filter then evap the water and weigh

I did activated charcoal clean-ups on some of my earliest extractions. Unless I'm missing something, there's no way that this is going to help with the defats. Even at the end of the process the charcoal wash is a PITA and is only effective for handling residues and minor amounts of plant fats and oils. I feel like this would ultimately just add a lot of carbon to your aqueous solution that would then need to be filtered out and only marginally reduce the amount of unwanted stuff compared to a defat. Granted, I've never attempted to use this for a defat, just given my experience with using it for re-x purposes, I'm highly skeptical.

Not at all I am afraid.

The solubility information is for freebase. You can find similar information for any other alkaloid that has a sufficiently high partition coefficient. On the contrary, the salt may as well be pretty much water soluble. In the hypothetical procedure you propose you assume that gramine fumarate will not be soluble in water, which is a huge assumption in my opinion.

activated charcoal is going to take out small ammounts of everything, but give its preference to heavier molecules and particulates. oils kinda fall in this category. it might not be the best way but its worth a try.

you should always wash your carbon many times with distilled water first so you arnt adding carbon powder. It also must be employed with a charmin plug filter. This kind of intense filtering could help with fats and particles a lot, the fats will stick to this filter material.

Its a little funky but worth a try, or this approach in general, perhaps using something else that will trap fats. rather than using so much nonpolar solvent(wasteful). This could be the initial dirty cleanup of nonsolubles.

AC is and old-school but still widely used in labs for decolorizing.
Typical pore sizes range from 1 um down to 20 angstroms, so tannins are easily trapped. since it is activated, it also retains charged molecules

rinse with EtOAc:MeOH, similar to rinsing a packed column, to pull out DMT first

Hi there. SWIM is now approaching the possibility of extract something from phalaris, or arundo donax, but before to experiment would be great for him to sit on the giant shoulders, and see if you already know this stuff:

how hygroscopic are the possible gramina salts? Like, 5-meo with HCl forms an orange, solid salt, while I know it gets a goo with 5-ho and spice, how does it go with gramine? That would be a starting possibility to isolate 5-meo.
And with other acids?

Also, to separate gramine from spice, I though about distillation, but since the temperature to reach would be too high, what about a vacuum distillation, that needs lot less? SWIM doesn't think this will burn spice.

And... well, any other tips?

For defatting, SWIM'll study out the AC way, sounds good to him. Thanks =)

swim is going to look into a sort of pH separation, akin to isoelectric focusing with proteins, but without an applied electric field..
it's not going to be easy

the other option is using binary solvent mixtures (gotta do some math for this one).

pH separation doesn't seem easy at all, and anyway would need some experiments.

What binary solvent where you planning to use?

Also, I was thinking: if gramine is insoluble in petrol ether, why not just pull out with that?
Also, what acid form a goo with gramine, but a solid salt with one of the 3 compounds we want(NN, 5-meo, 5-ho)?
Such an info would be greatly appreciated.

I think an aliphatic naphtha/heptane/hexane wash or recrystalization would get rid of all of those and you would have your pure dmt.

Check it out, gramine freebase is insoluble in pet ether (equivalent to aliph naphtha), and so is hordenine. Bufotenine freebase is also insoluble in naphtha.

5-meo-dmt, though, I dont know.. I could not find any solubility data on it.. Its xlogp shows its quite polar compared to DMT so I suspect it also would NOT be soluble in naphtha, but thats the kind of thing that only actual test can show because reality is more complicated than simple xlogp numbers, there's some weird exceptions out there and I dont know if 5-meo would be one of them

so well, just need to use pet ether to separate DMT and Gramine. It's already something!

5-MeO should be checked out, actually. Also, we should see if gramine is soluble in DCM, although I guess it is. If it's not, than we can get at least dmt and 5-ho, by using it.
for 5-meo, I don't know if it's soluble in dcm or not.