# Does DMT-Acetate become Polar in H2O, with added NaCl?

I'm extracting DMT (N,N-dimethyltryptamine) from Acacia confusa via acid/base. I extracted the DMT with $\ce{H2O}$ and acetic acid, converting it to DMT-acetate. Here, I used a non polar solvent, naptha, to defat the material, causing an emulsion.

I used $\ce{NaCl}$ to break the emulsion, this caused a thick layer of black tar to form on top of the aqueous solution, and a glossy black tar on the bottom of the vessel. I need to freebase the DMT acetate; however, I'm concerned that DMT-acetate migrated into one of the two polar layers. (Correction: Either the non polar layer on top or gunk layer at the bottom)

How can I confirm if this is so? Does $\ce{NaCl}$ cause DMT acetate (or any acetate) to become polar in $\ce{H2O}$? Why and how? Will the DMT acetate have migrated into any of these two polar layers?

• You are doing what?! Are you sure you have the proper permit to perform such operations? In A LOT of parts in the world you could get locked up for this. – Jori May 12 '15 at 20:20
• I don't need one. I am sorry to hear that you live in a place where it is a controlled substance. – Uga Duga May 12 '15 at 20:42
• Interesting. Where are you from? DMT is classified as a Schedule I drug under the UN 1971 Convention on Psychotropic Substances. – Jori May 13 '15 at 8:14

Does NaCl cause DMT acetate (or any acetate) to become polar in $\ce{H2O}$?

In aqueous acidic solution, that is in the presence of a sufficient amount of acetic acid, N,N-dimethyltryptamine is protonated. The acetate is the counter ion of the ammonium salt. The compound does not become more polar by adding sodium chloride!

Will the DMT acetate have migrated into any of these two polar layers?

Are you having two polar layers? I doubt it. You're having a top unpolar layer, the aqueous layer and some gunk.

Take the separated aqueous layer, neutralize carefully, extract with an unpolar solvent of your choice, dry over sodium sulfate, remove the solvent in vacuum. If necessary, recrystallize and determine the yield.

Please keep in mind that DMT is a controlled substance in many countries!

• Thank you so much for your quick and concise answer! My apologies. Indeed there was a top unpolar solvent saturated with plant tars hardened like a rock, the aqueous solution, and goo below. I have never seen any account of sodium chloride used in the Acetate state to enhance de-fatting. Most suggest using water only. Is the addition of sodium chloride at this stage is worth while? I am surprised with the quantity of plant material removed. After shaking the material heavily, the solvent was not recoverable, it turned into an inch thick layer of air filled tar... – Uga Duga May 13 '15 at 0:05
• Klaus I very much doubt that it is legal in any country in the world. It is regulated under UN schedule. I believe only some traditional tribes have legal access to it, but they certainly do not need any help. – Jori May 13 '15 at 8:18
• @Jori I know that it's Schedule 1 drug in the Single Convention on Narcotic Drugs, which, over time, has been ratified by quite a number of countries. Amazingly, the Vatican State is not among them. Anyway, I'm not a lawyer and I can't control who is in posession of a exceptional permit. Sometimes, strange things are required from students. I remember a student who was told by his professor to order morphine and use it as chiral base :D. Back in the days, students would have asked older group members for hints, nowadays they consult Chem.SE ;-) – Klaus-Dieter Warzecha May 13 '15 at 8:31