I like to learn every aspect about things before I do them. I would like to know why we add vinegar/citric acids to pull the alkaloids into the water if the dmt is already naturally in salt form: dmt tannin.

Wouldn't the addition of a salt pull something unwanted?

Thanks.

Yes and no. It all depends.

Natives don't add anything. They just use water and that works just fine. An acid is not needed at all. When you brew a cup of coffee or tea do you add an acid? Of course not, and you still extract the caffeine. Only certain alkaloids need to be pared with certain acids in order for their water solubility to increase.

Some alkaloids are more soluble in certain acids than in pure water, even when in salt form. But this is not true of all alkaloid salts.

For example, harmine hydrochloride is very poorly soluble in dilute hydrochloric acid. Its more soluble in pure water. But then harmine acetate is the opposite, it’s far more soluble in dilute acetic acid (vinegar) than in pure water.

The results depend on the alkaloid, the plant, and the acid of choice. So there is no one answer to your question.

To answer the question, the question needs to be more specific. We need to know the exact plant, the exact acid, and all the alkaloids in question. Without that information, there is no way to answer the question accurately.

I see.

LPlant: MHRB, powdered
Want to extract: DMT
DMT natural state: DMT tannin, an acidic salt.

The idea is that you want to make a form of DMT that is more water soluble than DMT tannate.

In this case, addition of vinegar would be a good thing. It's my understanding that DMT acetate is more water soluble than DMT tannate. Also DMT acetate is very soluble in vinegar. However, this would also make a lot more impurities get extracted.

Citric acid would be good. DMT citrate is very water soluble and also very soluble in dilute citric acid. However, as with vinegar this would also make a lot more impurities get extracted.

You would NOT want to use hydrochloric acid. DMT HCl is poorly soluble in hydrochloric acid. This is one of the worst acids to use in this case. You’ll likely get the most impurities using this acid and the worst yield.

You would also NOT want to use fumaric acid either. DMT fumarate is one of the least water soluble forms of DMT. Yields would be reduced, however contaminants should be reduced as well because many fumarates are insoluble in water.

Of these, citric acid or vinegar are the best choices. They will produce the highest yield, but at the cost of more contaminants.

Ok, cool. If you have time, could you explain the chemistry behind why adding citric acid would somehow kick off the tannin and replace it? Does it have to do with pka's?

Yes, a stronger acid with a lower pKa is able to split another salt made with a weaker acid with a higher pKa.

For example, DMT acetate can be converted to DMT hydrochloride by just adding hydrochloric acid, because hydrochloric acid has a lower pKa than acetic acid it will displace the acetic acid.

Ok, so for example absorbic acid will work because it has a pka of 4.2 and a pH of 2.2? I say this because acetic acid has a pka of 4.75 and pH of 2.4.

Yes, but I don't know how soluble DMT ascorbate is. It's all about finding a form of DMT that is the most soluble in water, or in the acid used. The best is usually vinegar.

In the dmt handbook avalible on here, they say that viniger(Acetic acid) gives substandard yields due to it forming a weak bond with the dmt compared to say phosphoric acid.

Is this not true?

That handbook is not telling the whole story.

Acetic acid (vinegar) forms acetates. Acetates are usually very water soluble, but also very unstable OUT OF SOLUTION and can easily come apart.

It’s true that the bond is poor OUT OF SOLUTION. But as long as there’s an abundance of acetic acid and it’s in solution, then it’s just fine. It’s only when it’s dried that it starts coming apart. At least that’s my understanding.

thank you

edit what do you think of using phosphoric acid?

SWIM like to know how soluble DMT ascorbate is, too.
A point on Calcium Ascorbate (Vitamin C) is that the ascorbic acid is an antioxidant.
It will, no shit, convert DMT-N-Oxide to DMT. That is, if Someone-I-Don't-Know-If-You-Know-Him-Or-Her makes teabags and boils it.

Bubble agitation.

DMT is more soluble in acidic water because it likes acidic water. It's actually really similar to the freebase/nonpolar phenomenom.

Mineral acids (HCL and other things with light metals) are strongly polarizing and, thus, have a dendency to make stuff more soluble in water. They will also blow that guy over there's shit up. 37% HCL makes this really caustic and kinda beautiful cloud when you open the bottle. It will turn pH strips red from a foot away. It's pH is a negative number and concentrated acid will nuke a litany of things. Same goes for muriatic. It's pretty tough, too. Dilute! Please.

Lewis acids (Vinegar, ascorbic acid) are kind of a tossup. Since they aren't a mineral conjugate (Like hydrogen) they can do weird shit. That's probably because they contain carbon or something. Sometimes a lewis conjugate makes a totally badass molecule pair, sometimes it's just too weak to hold on.

Maybe someone might actually measure these parameters.

Don't know about it’s solubility, but I do know that DMT phosphate absorbs into the body many times faster than the other forms do. So when making ayahuasca, DMT phosphate is one of the best forms of DMT to use. Better than DMT HCl, DMT citrate, and DMT acetate. I’m not sure why it absorbs so fast. But many ayahuasca users absolutely swear this is the case.

Phosphate is in itself physiologically active, being THE metabolic energy transfer moiety in the body. I think that's why it's an ingredient of cola drinks, too.

I am curious if there is a defined answer now to this search, it has been 30 months since this was posted.