Ok, this might be a bit of a dumb question, bear with me...

When salts are dissolved in water, they disassociate into their constituent ions, correct? (for example, sodium chloride disassociate into Na+ and Cl). I assume that this is what happens with, say, DMT citrate, with the salt disassociating into DMT and a citrate ion. Therefore, why does adding a base to a solution of DMT oxide not allow for freebase DMT to be extracted with a NPS, just like any other DMT salt? (because DMT oxide is just a salt with an oxide ion, right?)

Any insights into this would be much appreciated

i think in simple terms in the case of nacl the water molecules are capble of pulling the ions apart but in the case of oxidized stuff the force holding them is stronger and water alone cannot pull it so you need a molecule that can do that like zinc in the case of DMT oxide

DMT-N-OXIDE is not an ionic salt like NaCl. As I understand it, the oxygen forms a covalent bond with the nitrogen.

This bond is polar (because of the electronegativity difference between nitrogen and oxygen), that is why DMT-N-OXIDE won't dissolve in non-polar solvents and behaves more like a salt when it comes to solubility.

Thank you, that explains it!