I have a question concerning Soxhlet extraction, which I'd love to ask in another forum but I guess I have to ask here. Years ago I did an A/B using HCl, NaOH, and Chloroform. I knew less then.

Why is DMT-tannate soluble in isopropanol? With shredded MHRB, is isopropanol a decent solvent for Soxhlet extraction or would it make more sense to use acetic acid as the solvent, since that would 'hydrolize the cell walls?'

I understand that when people use IPA (hate that acronym because it makes me think of beer every time) in a Soxhlet, they then evaporate the IPA and dissolve the solid in an acidic solution, say, of acetic acid. This would yield DMT-acetate, right? And if one wanted, one could defat with a NPS at this stage. Then basify and extract for crystallization purposes.

What I don't understand is, how does it make sense to acidify (DMT-tannate -> DMT-acetate) then immediately basify? If all you wanted was the DMT-N, why would you acidify the DMT-tannate at all, since it is already a salt? Couldn't you just basify DMT-tannate and get a free base from that?

Basically I am just trying to decide how most sensibly to proceed with my Soxhlet in an MHRB extraction of DMT. It seems like yield would be better with aqueous acetic acid as a solvent but the boiling point is so high for that solution.

Clarification appreciated...

I guess that was, obviously, a series of questions. I hope that is OK.

where to start...

Tannic acid has many OH groups, and because of this, hydrogen-bonding readily occurs with the OH groups of alcohol.
using an acid, with heat, does induce hydrolysis on the cell walls. it is more effective
at this than using a soxhlet, which requires several hours of cycling.

People basify DMT Tannate when they do STB extractions. by doing so, they make DMT less soluble in water, and more soluble in the nonpolar phase. this also leaves behind most of the tannins, which have more solubility in the aqueous phase.

The A/B is a sort of isolation of alkaloids, by altering the charge state of the amine group.

OK.

So an acid is used initially mainly for hydrolysis purposes, rather than for the creation of a DMT salt in an A/B? And if one basified directly the resulting acidic extract, without defatting with an NPS, many of the unwanted compounds are more soluble in the aqueous, basic phase than the nonpolar phase and will stay in the aqueous solution? So there is some definite isolation that takes place without exposing the acidic solution to a non-polar solution? Could you discuss the compounds other than DMT (unwanted compounds), and their affinities in the basic, acidic, aqueous, and non-polar phases? I know this is asking a lot... But you seem to like informing us

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So, if one wanted to use a soxhlet because one was so inclined, would it be better to use dilute acetic acid as the solvent as opposed to an alcohol? I know it would have a much higher boiling point. I suppose my main interest in using the soxhlet comes from a sense that the physical material handling is a little easier, and it is possible to keep the working volume of one's solvents minimized. Is this misguided?

Would it be approximately equally effective to use an alcohol as a solvent but run the apparatus for a longer period of time?

3 Questions:

What is a tryptamine (in laymans terms)? (What is its relation to Psychadelics?)

Why don't the acid and base just neutralize each other/form a salt? or do they do both at the same time?

What does Hydro- mean chemistry wise? (I thought it meant water but: Calcium Hydroxide) does it mean Hydrogen?

Thanks for the detailed reply. I needed to do a bit of reading before I was able to really get it. I applied the same approach to calculate the amount of phosphoric acid solution necessary to get a pH of 5.00. please let me know if this is correct.

5.00 = 2.15 + log([H3PO4]/[H2PO4-])
~(-2.15)
2.85 = log([H3PO4]/[H2PO4-])
~(10^)
707.95 = [H3PO4]/[H2PO4-]

---

5.00 = -log[H+]
~(/-1)
-5.00 = log[H+]
~(10^)
10^-5 = [H+]

---

707.95 = 10^-5/[H3PO4]
~(*[H3PO4])
~(/707.95)
[H3PO4] = 1.41*10^-8

---

1.41*10^-8 mol[H3PO4]/L * 98g/mol = 1.38*10^-6 g[H3PO4]/L

10^-5 mol[H2PO4-]/L * 97g/mol = 9.7*10^-5 g[H2PO4-]/L

10^-5 mol[H+]/L * 1g/mol = 10^-5 g[H+]/L

1.38*10^-6 + 9.7*10^-5 + 10^-5 = 1.08*10^-4 g/L

1.08*10^-4 g/L * 100ml/25g = 4.34*10^-4 mL/L or 0.000434 mL/L

yess Ok Thank For /you!

It doesn't look like anyone's mentioned this, and if they have and I've missed it, I apologize.

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Hey everyone,

I figured this question would be best to ask here, although it can be applied to the A/B extraction of any alkaloid, it is also basic chemistry principles.

When doing an A/B extraction, what is the proper concentration in PH of both the acidic and basic solutions, as well as best way to calculate how many drops (or MLs) it would take to bring the PH to a certain range? i.e. If my alkaloids mixed with 10ml's of water came out to a PH of 6.5, and I wanted to acidify with 5% acetic acid (PH of 3.0), roughly how many drops would it take to bring the PH of my aqueous solution to around 4.5? Is there a way to calculate this? Or are you supposed to add a few drops and then calculate change in PH and keep adjusting this way until the desired level is reached? I assume it would be less time consuming if you knew the general amount of drops it would take.

Same goes for the basic solution with basifying. If my aqueous phase is now at a PH of 4.5 and i wanted to precipitate my base, how many drops of X concentration of sodium hydroxide or sodium carbonate would it take to bring the PH up to around 9? Is this a simple procedure or is the add and check method the one people use?

Lastly, when bringing the PH up or down, is it best to have a more acidic solution and use less of it, or dilute it more so that the PH is higher and then use more of it to gradually bring the PH down? for example, when acidifying aqueous phase down to 4.5 from 6.5, is it better to mix a dilute solution of HCL that is at PH 2.0 and use less, or mix a solution that is at a PH of 3.5 and use more?

These questions aren't based solely on DMT, so just following one of the TEK's and calling it a day is not really the type of theoretical answer I am in search of. Also, In various tek's on different alkaloids, a lot of people mention "just mix up a dilute solution of HCL and acidify, or just mix up a dilute solution of NaOH and basify until you see a precipitate". I think I would like to be more specific as to what is going on than to just mix up a basic/acidic solution and just start pouring it in without having an idea of how fast of a PH change we are expecting.

I'm not sure if these are difficult questions, as I am just starting to learn O-chem after finishing general chem. Thanks in advance for any help.

A change of 1 in the pH represents a ten fold change in the concentration of protons. When dealing with a strong acid this makes pH easy to calculate, it's just the negative log of the the molar concentration of the acid since it almost completely dissociates, so a 10 fold change in concentration produces a change in pH of one. For weak acids the pH is =-log((-K+sqrt(K^2+4KC))/2 where K is the Ka of the acids (10^-pKa) and C is the molar concentration, K is much smaller than C in most cases so you can just use -log(sqrt(KC)), so it would take about 100 fold change in concentration to produce a change in pH of 1. In reality when performing extractions the various chemicals in your plant material tend to buffer the solution so it takes more acid or base to change the pH than you would calculate from that formula. Changing the concentration by 100^(desired change in pH) would be a good starting point if you're using acetic acid. Then check and add more as needed. Works the same with bases, you can find the pKa from the pKb if you know that(14-pKb=pKa.

It depends somewhat on the situation, usually I use the strongest solution that I don't think will damage whatever product I'm aiming for as less solution is easier to handle and usually gives better yields. For DMT I try to stay below 13 and in positive numbers, though some people add straight lye and it doesn't seem to cause too many problems. Using a more dilute solution is sometimes better for precipitation, it seems to make the crystals form more slowly and grow larger and more pure.

Hello Everyone! I'm new here and I'm just loving the amount of knowledge there is available on here on the chemistry of psychedelic compounds. My objective is to do more than just follow a recipe and really get into the science. To all the chem savvy members of this site please help me with this problem I've been trying to solve. This is considering the natural salt forms of DMT in MHRB. So it's hypothesized that DMT occurs as DMT Tannate, but it may also exist in other various salt forms. Especially considering that tannins are polypenols and exist in hundreds of different forms, All sharing the relationship that the are polyphenols and can form esters. Specifically I want to talk about this tannate salt form and the chemical structure. I can't find any literature or pictures of how DMT Tannate would look. I also can't find any proposed mechanism of the STB reaction. I put my brain to work and drew 3 proposed structures. Gosh I wish we had the IR and NMR spectra for these salts! So... Which one is right?

Note: Blue is negative charged, red is positive. Also, Tan means stands for tannate and the negative charge comes from an oxygen anion that used to be a phenol.

This first one is the Ammonium Salt. Psilocybin exists as an Ammonium salt in natural form, Also in TIKAL Dr. Shulgin uses a DMT ammonium salt. So DMT can exist in this form, but does it exist like this as a tannate salt in nature?


The second is most likely the correct form, it looks just like an HCL salt would look like.


The Last one I'm pretty sure is incorrect. Can it hydro bond?


Sorry if I posted this in the wrong place. It just seems like there are people that know chemistry on this thread that can help. It just gives me a higher chance of getting this seen and answered. Please help advance our scientific knowledge of these chemicals! Thank you all for your time and help.

Is oxalic acid present in mimosa? There are different alkaloids in nature that are present as oxalates, so that could potentially be another of the natural salt forms of mimosa.

Is it possible that different parts of the plant have different concentrations of acid and therefore different salt forms? Im not sure how possible it is to isolate an alkaloid in its natural salt form and get an NMR spectrum for example.. how would one go about that? Because even if you do, say, a water soak, this could already change the salt form if there are different acids in the plant, and a stronger acid from another part of the plant gets in contact with the DMT.. Anybody got any idea how they find out the natural salt form when researching plant chemistry?

Thanks for posting and welcome to the Nexus, btw

I could not find anything about Oxalic acid being present in M. hostilis. Then again I can't find much scientific literature on this plant. However DMT Oxalate seems like it could happen also. It shares kind of the same characteristic with tannin. Such that it will bond to DMT through an ester and the acidic end is the carboxylic acid, just that tannin may have a long chain of subunits between O-CO-[Rn]-COOH. "Is it possible that different parts of the plant have different concentrations of acid and therefore different salt forms?" This is a great research idea!!! We need more scientists looking into this!
I also gave this some more thought. DMT salt won't dissolve in organic solvent because it is polar. In a polar solvent such as water, the DMT salt will be dissociated by water. Now just because the salt, lets say Oxalate, got removed from DMT it doesn't mean it's still not present in the water solution. I 'm guessing one would just need to seperate all the compounds in the solution and then determine what salts are present, then one can say what salt form DMT may exist in natural forms. Now how someone can go about this I dunno. I'm still an undergrad and highly considering going into psychedlic research like this.

..Dennis McKenna once commented that tryptamine alkaloids were usually present in plants as the salts of Krebs cycle acids..
.i don't think tannic acid is widely distributed in the plant world (other tannins are) and i haven't seen any evidence of DMT-tannate anywhere in literature..
.

salts of kreb cycle acids? that's very vague
could be citrate, fumarate, succinate, or malate slats

I wonder, why are you trying to solve such a problem? Just asking because it is meaningless; in a dry tissue such as mhrb all sorts of salts will form between the dmt and whatever is negatively charged. That includes tannins, kreb cycle acids, phosphates, chloride, sulfate, etc. And in wet tissue there often not such thing as "salt", as long as it dissolves and dissociates. All this salts talk matters very little actually, unless you have something in mind which is hard to guess!

As for your diagrams, the first is totally incorrect since it represents a covalent bond between tannins and dmt (and this is vaguely positioned on 4th position of the indole - why not the 5th or the 6th?!?!), the 2nd is correct-ish and the 3rd is also wrong - dmt can sure form hydrogen bonds, but what you drew is not a salt.

I disagree, I don't think it is meaningless. I believe that we should be able to have data analysis of the compounds present in these sacred plants. You just never what you're gonna find. The thing is that we really don't know much about these plants and I'm looking at the whole picture not just the salts of DMT. Also since it can form differnt salts that means that each salt has minor but different chemical properties. WHen you look at the structure of psilocin it only differs from dmt by having a phenol at the 4th carbon. Also thanks for your opinion on the diagrams I made. I think the second one is closest to the right thing.

You mean a hydroxy in the 4th position, not a phenol, no?

Im not sure about your argument though, sure psilocin only differs by a small modification, but as we know, small modifications in the molecule structure can make for completely different effects (or change from big effects to no effects, like say with LSD to some of its isomers). But the difference between two salts of the same molecule is not the same as the difference between two different molecules.

Im wondering what is the practical use for this kind of knowledge you are trying to have? Even if you know some of the different salts that are in a plant, this doesnt really tell you much practically, when you're gonna use the plant, because as soon as you have it in an acqueous solution, for example, this is gonna completely change the whole story, because the salts would dissociate, and even if you dried the solution up, then you would have the alkaloids forming the salt with the strongest acid, not anymore the diversity that might be present naturally in the plant, AFAIK. And the effects would all be the same from the parent compound. And it will all turn into HCl salt in your stomach.

So do you see any use for knowing the salts?

I'm still unconvinced with regard to what the knowledge of dmt salt in mhrb would help you to. Sure different salts have different solubilities (and maybe different effects) but what this has to do with dry mhrb powder? whichever way you go with mhrb, be it an A/B, STB or drytek you'll immediately nullify the whatever salt dmt in mhrb is.

It would make sense if you were trying to pull dmt salt(s) from dry mimosa powder using a solvent such as ethanol, IPA, acetone, but for all the salts the best ever solvent is plain water. Can you provide an example where such knowledge would be useful other than the "knowledge" factor? Like sure one can study and elucidate how the small 5th toe on our feet develops and forms, but hell, is that a burning issue at all or even something of important medical relevance?

Yes a hydroxy in the 4th position. But when an OH is on a ring it's a phenol, that is slightly acidic right? O k so knowing the different salts is useless, at least for extraction purposes and tripping. The reason for posting here was because i'm interested in the structures that these salts would form, particularly a tannate salt. I really believe more research should be done. This is why I'm so interested I really want to know the compounds in the root not just the psychoactive ones. I just feel like when this plant was researched it was just to find the active compounds and everything else was sorta ignored. I believe the magic is just not in the active compounds but all the compounds in mimosa hostilis. Plain and simple I think there's something hiding in that plant that can really help people, (not saying that dmt doesn't help people cuz I do believe it does), but something a lot deeper.