Steps taken:

50g powdered MHRB
added approx 400ml distilled water (from gallon jug from supermarket, (did not measure ph))
heated to ~170F
did 2x freeze/thaw/heat cycles

Now- before adding vinegar the ph is around 3.6

Adding 50ml vinegar does not make a measurable change, and it still is around 3.4

According to the excel calculator I downloaded from the site, anything under ph 6.5 should result in 99% being in salt form. So if you are already below 4 then why add vinegar?

I find it hard to believe that everyone else uses some kind of water that results in the MHRB turning the solution to a ph above 6, and previous extractions with this tek yielded good results, with 50ml vinegar; this time 100ml was added but had negligible effects on the ph between first 50ml and second 50ml added. (Obviously 5% vinegar would not have a large effect on something with an already acidic ph) So...

1) what is the point of adding the vinegar then? if the ph is already acceptable?
2) Is it the acetate group specifically we are going for?
3) Assuming vinegar is not necessary, what form would the anion take without the vinegar?



Thanks so much for the assistance everyone

Plant matter is variable.
The vinegar is not always needed but it basically guarantees that you got it all in salt form.
Also

Im not sure how much this applies here but most plant acids are actually weaker than acetic acid (its one of the strongest organic acids). I dont really know the usual salt of DMT in plant matter.
But if its something like oxalic acid it would improve the solubility.
Its usually not always fixed how much alkaloids are in freebase or salt at a given time in the plant.

My idea (maybe wrong) from General Methods of Extraction and Isolation of Alkaloids:

Because the vinegar converts potentially hard-to-break DMT salts to acetate, which is easier to liberate into its freebase form.

Natural plant salts such as tannates or oxalates ar hard to freebase even with a strong base like KOH.

So it may not be just about pH.

I dont think its like that entirely. The tannate salts dissolve better if theres lower ph so they can be cleaved easier. But I dont think they will swap places with vinegar because its too weak.
You would need something like HCl to break and swap that.

It also depends on the size of the tannate or oxalate crystals (how soluble are DMT oxalate and tannate anyhow?), the temperature and the time allowed for dissolution. The acetate then provides a more amenable counter-ion during this process.

We only have to break up the ion lattice of the salt, not covalent bonds like in an amide.

Then there's the common ion effect. If the pH is due in part to oxalic and tannic acid, DMT oxalate or tannate won't dissolve so well. Adding acetic acid would then help us get around this, perhaps.

I wonder if adding calcium chloride after acidifying and soaking would increase the extraction efficiency by binding up tannate and oxalate?

I am basing that statement on the article General Methods of Extraction and Isolation of Alkaloids:



This is interesting since STB teks are quite effective and many people have even success with moderate bases like Ca(OH)2 in "food-safe" teks.

Look at 1.7.2