Concepts of an A/B

[aliendreamtime]

Hey folks! I've heard a few people asking about the chemical concepts of the A/B. I'm not sure if something like this is already on here, I hope I didnt waste my time! LOl

Feel free to ask about anything thats unclear and I'll answer you and revise the lesson.

 

[SnozzleBerry]

Nice work! Thanks for putting the time in and sharing

See Also:

Entropymancer's DMT Extraction Overview

Dozuki's Art of Liquid-Liquid ext. The Basics

 

[Ambivalent]

thanks everyone. great information chewed up for easier understanding.

 

[Ambivalent]

Hey folks! I've heard a few people asking about the chemical concepts of the A/B. I'm not sure if something like this is already on here, I hope I didnt waste my time! LOl

Feel free to ask about anything thats unclear and I'll answer you and revise the lesson.

one thing im little confused about. you mentioned that dmt is in freebase form in the bark and therefore is insoluble in water and has a negative N atom free. my understanding up until now was that the conditions of the bark inside are somewhat acidic and dmt is water soluble.

 

[aliendreamtime]

Haha yeah I also would like to add that anyone who has more information that would like to add on (or correct me for that matter) feel free to chime in or I'll send you the word doc to make changes if you'd like.


I'm not sure about the conditions within the bark, I assume that could be tested with a ph meter in a room temp suspension of ground bark with distilled water intif anyones interested.

I imagine that if the conditions inside the bark were acidic, the nitrogen wouldnt have a negative charge (lone pair of electrons) and would have a H attached, due to the abundance of H+ protons in an acidic environment. Realistically though, I think this depends on the pKb's of whatever molecules are available for protonation within the bark.


As far as the solubility, I think it depends more on temperature. As water is heated, the molecules themselves become more energized, and spread further apart as a result, making hot water a 'less picky' solvent than cooler water. So hot water will dissolve more of what isnt particularley soluble in water.This is true for most solvents I believe.

However, solubility is really a spectrum, with plenty being partially, slightly, highly so
luble solutes in a given solvent.

Its also known that CWE brew like Jurema can be made from just bark.

But if the conditions inside the bark are indeed acidic, then maybe the DMT in the bark isnt freebase? I was under the impression it was, I'll have to check that if I can.

Perhaps DMT is slightly soluble at room temp water, and reasonably soluble in hot water, corroborating the fact that you need 30+ grams of bark for Jurema, but only 5-10 in a multiple wash boil. I use lemon juice just in case haha. In that case the initial
acidic step isnt completely necessary, but simply helps to protonate every last molecule of dmt to improve solubility?

Anyways I really only made this because it finally hit me that the strong NaOH solution deprotonates the amine, leaving the molecule almost nonpolar, and thus soluble in nonpolar solvents...adding and acid makes it polar and therefor soluble in water. But I wanted everyone to have a chance at understanding.

Send me a source if you can.

Peace

 

[SnozzleBerry]

But if the conditions inside the bark are indeed acidic, then maybe the DMT in the bark isnt freebase? I was under the impression it was, I'll have to check that if I can.

Afaik, dmt (and most other alkaloids) exist in a salt form within the plant material, not freebase. This has been discussed in a number of posts, but last I checked, there was no literature that had been found that verified this in the case of mhrb (it's possible I missed relevant threads/discussions in which it was presented).

 

[aliendreamtime]

Interesting Snozz,I'm not wed to the idea that they're freebase in the bark I'll have to change that. But then, what would be the point of acidifying the water to help get the alks out?

 

[Ambivalent]

It is quite normal and logical actually. Plants need the substances to be water soluble, so they can transport them to the various parts of the plant, i guess.

i read here on nexus that mhrb contains tannic acid, so i guess it can be as a tannate salt. now why adding acid before extracting. maybe other salt form that we use to extract are more water soluble than dmt tannate ?

 

[SnozzleBerry]

i read here on nexus that mhrb contains tannic acid, so i guess it can be as a tannate salt. now why adding acid before extracting. maybe other salt form that we use to extract are more water soluble than dmt tannate ?

The hypothesis that's been discussed on the nexus is that it's tannate, but as I said earlier, afaik, no literature has been found that actually shows this to be the case.

The purpose of acidifying the bark is to help lyse the cells and improve the efficiency of the extraction. Alkaloids are located within the cells and acid, heat, pressure, sonication, etc. are all just means to the end of breaking cell walls to get at the goodies.

 

[aliendreamtime]

Ah breaking cell membranes, I wasnt sure if acids would do this. Good call. Also H3O+ is more polar and would help pull the based trypatamines out no?

I'll revise today.

Thanks gentlemen/women

 

[Ambivalent]

i read here on nexus that mhrb contains tannic acid, so i guess it can be as a tannate salt. now why adding acid before extracting. maybe other salt form that we use to extract are more water soluble than dmt tannate ?

The hypothesis that's been discussed on the nexus is that it's tannate, but as I said earlier, afaik, no literature has been found that actually shows this to be the case.

The purpose of acidifying the bark is to help lyse the cells and improve the efficiency of the extraction. Alkaloids are located within the cells and acid, heat, pressure, sonication, etc. are all just means to the end of breaking cell walls to get at the goodies.

its another reason yes. but if the bark is processed and pre powdered, than this lysing of cell's is more or less unimportant. it seems that with pre powdered bark alot of this cell structure is destroyed. but in any case, acid increases solubility of the dmt salt in water IMO, so even with pre powdered bark it benefits in some way.

 

[SnozzleBerry]

if the bark is processed and pre powdered, than this lysing of cell's is more or less unimportant. it seems that with pre powdered bark alot of this cell structure is destroyed.

Afaik, powdering/grinding plant material is a very inefficient method for lysing cells. There are a number of papers on RNA extraction that essentially mention this when using grinding to prepare material for further cell disruption (lysis). This tutorial elaborates on it (note that most plants have strong cell walls).

 

[Ambivalent]

im sure its not the most efficiant way of doing it, but there is obvious difference. And is very easily observed :

"For example you soak 100 g of whole bark pieces in half a litre of water, and in a different container soak 100 g of pre powdered material. The difference can be observed with naked eye."

The pre powdered material is extracted very easily with water only. This for me is good enough indication, and this is only as far as it goes with mimosa bark experiments. I am sure there are plants with even stronger cell structure otherwise.



ps.

thanks for the paper you posted.btw, looking for a second through it i saw that the main disadvantage in mechanical cell disruption is that it destroys cells completely and alot of the unwanted material in the cells is released in solution. which means more work for filtering and purification, again depending on the wanted substance.
in our case this thing isnt a drawback, at least in my experience.

and the thing is, theres always a combination, a chain of processes to get the job done. freezing, heating, acidifying, even mechanical disruption if needed.

 

[SnozzleBerry]

"For example you soak 100 g of whole bark pieces in half a litre of water, and in a different container soak 100 g of pre powdered material. The difference can be observed with naked eye."

The pre powdered material is extracted very easily with water only. This for me is good enough indication, and this is only as far as it goes with mimosa bark experiments. I am sure there are plants with even stronger cell structure otherwise.

Certainly...but in the case of adding acid to your water, is it further lysing cells, increasing solubility of the alkaloids or both? I'd lean towards both, but it would be cool to be able to verify this

thanks for the paper you posted.btw, looking for a second through it i saw that the main disadvantage in mechanical cell disruption is that it destroys cells completely and alot of the unwanted material in the cells is released in solution. which means more work for filtering and purification, again depending on the wanted substance.
in our case this thing isnt a drawback, at least in my experience.

and the thing is, theres always a combination, a chain of processes to get the job done. freezing, heating, acidifying, even mechanical disruption if needed.

Agreed, glad you found it to be of use. I thought it was a pretty good and concise write-up.

 

[Ambivalent]

Agreed, glad you found it to be of use. I thought it was a pretty good and concise write-up.

yea, thanks again. it cleared the fog of certain things for me. still a newbie to this world. still expanding my views.

 

[nen888]

..re the salt form of DMT in plants:
sorry i don't have refs handy, but almost all plants contain some form of acid, hence alkaloids are almost always in salt form in the plant..plants have to have a certain acidity to be able to take in water..Dennis McKenna once commented that DMT is usually present in plants as the salt of various krebs cycle acids..
..so, it is not essential to acidify the solution, however, to 'break' the alkaloids off other molecules (like tannins) further acidification may be required..

as far as the DMT-Tannate thing goes, after a lot of research i believe this is simply an internet-myth..i have never seen any evidence for this claim, nor has tannic acid (which is just one of many kinds of tannins) been reported from M. hostilis..in fact tannic acid is not massively widespread in plants (tannins are though)

thanks for all the work and thought aliendreamtime..

 

[Ambivalent]

..re the salt form of DMT in plants:
sorry i don't have refs handy, but almost all plants contain some form of acid, hence alkaloids are almost always in salt form in the plant..plants have to have a certain acidity to be able to take in water..Dennis McKenna once commented that DMT is usually present in plants as the salt of various krebs cycle acids..

this makes alot of sense to me. today i was also researching on this matter and stumbled on a phytochemical profile of jurema preta or mimosa hostilis. in this study there were mentioned all these forms of acids which were unknown to me. i will try to find the paper, it had a good amount of information.


edit : i found the paper i was reading, but i was wrong about one thing. these forms of acid i read on the paper are not from tenuiflora. but from a plant belonging to the Asteraceae family. Anyway heres the link of the paper, cant be downloaded though.

http://www.docstoc.com/docs/122663878/Phytochemistry-of-some-brazilian-plants-with-aphrodisiac-activity

 

[nen888]

..just posted on salt form of dmt in acacias in Trying to Improve Acacia info thread..
mimosas are, of course, 'cousins', if you like, of acacias..here's the info..