endlessness wrote:2- Sort of, but sodium is an element, not an alkaloid. But yes you are correct in your intuition that DMT is just the DMT molecule, and DMT acetate is DMT with an acetic acid ion attached to it.
This is not entirely correct actually. There is a difference between a freebase DMT molecule and a salted or
protonated DMT molecule and it explains the differences in solubilities. I hope that I can explain this a bit below, not so much for the sake of correctness, but for the sake of understanding of the mechanisms.
In the scope of this discussion, we could simply say that an acid is a molecule that can be split into two parts; a positively charged hydrogen atom, H+, also called
"proton" and a negatively charged part such as Cl- (chloride ion), C2H3O2- (acetate ion) etcetera.
In general, with acids and ions it works like this: When Na (sodium metal) reacts with HCl (hydrogen chloride), the hydrogen proton from the acid is given off as a gas, as if it passes on its "+" ion quality to the sodium metal and returns to it free elemental form, while the sodium is now ionized as Na+. When NaOH (sodium hydroxide) reacts similarly, H2O (water is formed from the liberated H+ proton. In this case, the sodium was already ionized as Na+, but it is accompanied by a negatively charged OH- (hydroxyl ion) that can recombine with the H+ proton into neutral H2O (water).
With DMT it is slightly different than with sodium. [blink] Now here comes the crux of the explanation [/blink] ->
The freebase DMT can actually incorporate a proton! The part of DMT that makes this happen is the amine part. When the amine part of DMT binds to a H+ proton, it becomes an "ammonium" part and the DMT is now formally called a
"dimethyltryptammonium ion" and it bears a positive charge, that it got from the proton. Another way that this is named is to say that the freebase DMT has become
"protonated". The DMT molecule has actually changed a bit and has has also acquired an electrical charge.
This positive charge is balanced by the negative ion that used to be related to the former lone proton. And just like with the acid, the positive and negative part can be bound together, or freely float apart in a solution. When it is in a watery solution, it will be mostly floating apart as separate positive and negative ions.
The ionic character, due to the positive charge, of the protonated DMT causes the difference in solubility with freebase DMT, which has no such ionic charge. While the freebase DMT molecule is generally liked by "apolar" (neutrally charged) solvents, the protonated DMT is very much liked by polar solvents, that have a more positively charged part and a more negatively charged part that likes to be around the charge of the protonated DMT.
The DMT as it is naturally occuring in living organisms is protonated and paired with some negative anion such as an acetate or a tannate ion. This form is soluble in water.
When you "freebase" (verb) this natural form of DMT with NaOH solution (which is actually a bunch of Na+ and OH- ions), the protonated DMT loses its H+ to the NaOH's OH-, forming water (the Na+ balances out with the anion that came with the DMT "salt" ). The now
deprotonated DMT has lost its charge and is no longer very attractive to the water. But if there is some apolar solvent nearby, it will like the deprotonated "freebase" (adjective) DMT.
The reverse process is when you have freebase DMT dissolved in some apolar solvent and contact it with a polar solvent containing an acid that can give off a proton (eg. vinegar). When the DMT meets an accepts a free proton, it no longer wants to be in the apolar solvent and instead moves to the polar solvent.
As a final note, I am not a certified chemist, so I might not be getting all the details exactly right. In fact, as little as I know, I do know that it is much more complex in practice than it seems in theory. But the above explanation might at least help you understand a little bit of the mechanics behind some of the teks.