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Freebase to tannate?

Migrated topic.
dooby

dooby

Rising Star
Hello,

In an acid/base extraction the vinegar breaks up the dmt-tannate(s) to form dmt-acetate...

This is then freebased with NaOH and pulled with a non-polar solvent...

What if some of the tannins get pulled into the non polar solvent as well? What is keeping them from forming dmt-tannate in the nps?

The only reason I could think of, having no chemical background whatsoever, is that the freebase molecules, or the tannins, become inert in the nps - although I can't imagine why...

Anybody?

PLUR

PS: If this freebase to tannate conversion actually could happen, what would be the consequences? Could it lead to a new understanding of different colors and textures of spice?
 
from another thread

when you raise the pH of the solution, the charge state of DMT's amine shifts from positive to no charge. in this state, it isn't possible for electrostatic interaction, that is, charged particles can't bind it, forming a complex. that leaves the only other two options for molecules to bind to it: hydrogen bonding with the indole amine's hydrogen (polar..relatively weak), and van der waal's (nonpolar...stronger) interactions with indole.
Click to expand...
what this means is tannates won't form in the nonpolar solvent, but may be present by other interactions.

so to decolorize, you may pour the naphtha through activated carbon, filter it, and add clean naphtha to elute any dmt free base that may be embedded in the carbon. the tannins will adhere to the carbon.

alternatively, you may do freeze precipitation, filter, then recrystallize with a small amount of hot heptane or hexane. the resulting crystals will be white or very light yellow.
if the crystals are exposed to air for some time, they will turn yellowish; this even happens
to tryptamine base, it is oxidation occurring at the amine.
 
Thank you benz for your answer...

I am not sure I completely understand though...

I read about freebasing dmt-acetate by applying heat, and that this was not possible because the molecule, once freed from it's acetate form, would turn into a tannate again and that this could only be resolved by re-basing...

So, I thought that if formation of dmt-tannate could take place in the nps some of the jungle and jimjam spices might be, at least partially, attributed to the presence of tannates...

The question was purely theoretical, as I will be re-basing the vinegar I used to salt the alkaloids out of my naphtha ;)

I had already fridge-precipitated some alkaloids before deciding to go with the vinegar-salting, and what was yeilded from the fridge needs no discoloration whatsoever - I'm very curious as to what will come out of the rebased vinegar/naphtha pulls...
 
dooby said:
I read about freebasing dmt-acetate by applying heat, and that this was not possible because the molecule, once freed from it's acetate form, would turn into a tannate again and that this could only be resolved by re-basing...
Click to expand...

any non-charged form of tannic acid and its derivatives cannot form salt complexes with DMT in a nonpolar solvent that is immiscible with water. they may only associate by nonspecific interactions; that is, association by proximity.

that being said, there are a number of ways to separate said molecules from DMT...recrystallization, chromatography, or as I mentioned, decolorization.
 
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