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DMT extraction question


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#1 SlipperyJack

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Posted 03 April 2021 - 12:20 PM

I recently developed an interest in exploring DMT.

I was a bit overwhelmed with the complexity of it all, but after doing a bit of research (thanks for some videos from Chris Cantelmo), I realized that it is actually quite simple.

So I am pretty sure that I understand that purpose of each of the steps, enough so that I can get through my first extraction, at some point.

But one question keeps popping into my head:  How is the DMT targeted by the extraction?

No doubt there is a lot more in the MHRB than just DMT.

The vinegar and the heat must release other stuff.

How is it that just the DMT migrates into the naphtha?

Is it related to the pH?

 

While not critical to the success of the extraction, it will be a while before I will be able to commit time to this experiment... so until then, I am just trying to learn as much about the process as possible.

 

Thanks for any light you can shed.

 


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#2 YoshiTrainer

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Posted 03 April 2021 - 02:39 PM

Hopefully this helps!

https://mycotopia.ne...s/#entry1480707

#3 SlipperyJack

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Posted 03 April 2021 - 02:50 PM

 

I read this the other day.

I just read it again.

So in the context of my original question... is DMT the only 'salt' that is present in MHRB?

Or, would there be other salts that end up in the crystals alongside the DMT?


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#4 Norman

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Posted 03 April 2021 - 04:36 PM

Hopefully Phin will jump in here and put some specifics to the vague generalities that I’m about to post but here goes-
What we’re doing here is isolating a molecule from among many by playing with solubilities. DMT is present in MHRB - to use an easy example - along with lots of other chemicals, other alkaloids, acids, fats, proteins, starches, etc. DMT is present in MHRB as probably DMT tannate saltt because MHRB contains a lot of tannic acid. DMT tannate is somewhat soluble in water and we make it more soluble by adding a large quantity of another acid the DMT salt of which is very soluble in water, say acetic acid in distilled white vinegar. After boiling and straining you have a solution that has only water soluble material left in it but still with a lot of stuff that is not DMtT. Some of that stuff is other alkaloids that have converted to acetate salts and some of them are psychoactive. If you drank some of the solution with an MAOI and then compared the experience with taking an equivalent dose of extracted DMT with an MAOI you would see the difference very clearly.
Some plant material contains a large amount of fat which can come over in the solution because though it isn’t actually soluble in water it’s a liquid when hot that can come through the filter. MHRB doesnt have this problem but for plants that do the solution is defatted with a non polar solvent which isn’t miscible in water.
So at this point we’ve removed the DMT from the bark into the water, removed the water from the solids, and removed the non water soluble fats and oils from the water.
Now we basify the solution to convert the DMT and any other alkaloid salts to their freebase state, making them insoluble in water. Some alkaloids will clump together enough to precipitate out at this point and they can be collected by simply decanting the solution off of them. DMT and other MHRB alkaloids won’t, so we have to remove them from the solution with more NP solvent which the alkaloids are now soluble in. How we do this is where the refinement comes in because of the varying solubilities of the different alkaloids in different types of solvents at different temperatures.
Naptha has become the standard because DMT and similar alkaloids are very soluble in it when warm and not very when cold so it extracts well and is easy to freeze precipitate. If you evaporate your naptha you will get a far different product than the precipitate.
The alks are more soluble in xylene and won’t freeze precipitate at all and more of the alkaloids in the solution are soluble in it so you get a much broader range. This is why xylene is often used at the end of an extraction- to get everything that the naptha left behind. Methylene chloride and chloroform are even more broad spectrum. Lighter solvents like heptane are much more selective and can be used to separate broad spectrum extractions into their components through temperature control and crystallization.
Acetone is extremely broad spectrum but is miscible in water and so can’t be used in an A/B but is often used in dryteks. The fumerate salt of DMT is not soluble in acetone so if you dissolve your extracted DMT in acetone and add it to fumaric acid saturated acetone, near pure DMT fumarate will precipitate out. 5MEO DMT fumarate is soluble in acetone so people use this method to separate the two when dealing with a plant that contains both.
So anyway that’s how it works. You just get rid of more and more stuff by playing with the solubilities until you have a workable amount of concentrated alkaloids that you can play with and fine tune into anything from gooey red jungle spice out to pure clear freebase crystals. Whatever you like.
When you do extract, don’t throw anything away. Label it and hang onto it until you’re sure you’re done. I’d go with a standard A/B using naptha and a freeze precip like Marsofold’s and don’t try to do too much bark at once. Easy things become a pain in the ass with large volumes. 100 grams of MHRB will give you a gram of DMT if you do it right. Save some bark back for a second go around once youve ironed out the kinks.
Hope this helps. Good luck and be safe.
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#5 SlipperyJack

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Posted 03 April 2021 - 06:18 PM

Thanks Norman.

 

I think that help a lot.

So, basically, there is a lot of stuff that we boil out of the MHRB, but because we use naphtha, pretty much only the DMT crosses over to be crystalized?  Other solvents would result in other compounds crossing over?

That's what my non-chemist brain took from that... and if that is anywhere close to accurate, then that is enough for me, at this point!

 

Thanks again.


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#6 Norman

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Posted 03 April 2021 - 06:58 PM

Yeah pretty much. Naptha seems to be in the sweet spot for DMT selective solubility and a few things adjacent depending on the temperature.
In a nutshell you’re removing as much NP soluble material as possible while the alks are in salt form and then converting them into NP soluble freebase before extracting.
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#7 SlipperyJack

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Posted 04 April 2021 - 09:40 AM

Thanks so much.

 

Another question has popped into my head.

Many techniques use heat to pull the DMT out of the MHRB.

Is it possible to over-boil?

Or, more specifically, is it possible to boil it in water for too long and risk losing the DMT to evaporation or breakdown due to heat?

Mr. Google told me that the boiling point of DMT is 160*C.

So as long as I keep it below that, theoretically, I can keep adding water and simmering for as long as I want?



#8 Phineas_Carmichael

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Posted 04 April 2021 - 12:18 PM

Hopefully Phin will jump in here and put some specifics to the vague generalities that I’m about to post but here goes...

Norman pretty much got everything I would have said in that post. The only specifics I could add would be to start drawing the molecular changes & I wouldn't do that to you (unless you want me to)

That 160°C figure that Mr. Google gives is for a DMT salt (which one I do not know) and is higher than the BP of water so as long as the pH is less than 6.68 it can't get hot enough to hurt the target molecule. The only danger is walking away, getting stoned, & forgetting about the pot on the stove for so long it boils dry and burns.

The freebase, however, has a BP of around 80°C so we need to be more careful in the basic portion of the extraction & make sure everything has cooled down sufficiently before we convert to the freebase.

Edited by Phineas_Carmichael, 04 April 2021 - 12:22 PM.

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#9 SlipperyJack

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Posted 04 April 2021 - 02:52 PM

The only specifics I could add would be to start drawing the molecular changes & I wouldn't do that to you (unless you want me to)

 

Thanks for your insight Phineas.

 

If you have the time, please go ahead and do it!

I may not get it, but I'm willing to give it a try.



#10 Norman

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Posted 04 April 2021 - 04:12 PM

Second that.

#11 Phineas_Carmichael

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Posted 05 April 2021 - 01:34 AM

Ask and ye shall receive, but don't say I didn't warn you! Also please excuse my terrible penmanship and the dull state of my sharpies...

Here comes your totally unnecessary Organic Chemistry Lesson
I'll walk through a standard Acid/Base extraction of DMT using Acetic acid aka Marsofold's Tek
=====
This here is freebase DMT - C12H16N2 - Go ahead and count the atoms.
Structurally it is composed of a large indole ring on the left, and a tiny little carbon tail on the right:
1 - DMT.jpeg
Each line connecting atom to atom indicates a covalent bond, double lines indicate double bonds.
Notice how each carbon atom has 4 bonds, each hydrogen has 1, but each Nitrogen has only 3. This is because Nitrogen likes to keep a pair of electrons in it's back pocket, just in case. We call these a "lone pair" because they aren't bonded to anything and they form the basis of the entire process.
The Indole ring is flat like the paper it is drawn on, but the carbon tail is actually 3-dimensional so the solid triangles indicate the bond is sticking out of the paper towards you while the dashed triangles indicate the bond is sticking out of the paper away from you.

That's a really bulky way to draw it though, so we leave off all the pesky hydrogens and just draw the basic skeleton and assume that each vertex is a carbon (unless otherwise noted) atom with enough hydrogens on it so that each atom has the right number of bonds:
2 - DMT Simplified.jpeg

Same thing goes for Acetic Acid (vinegar):
3 - Acetic Acid.jpeg
That thing on the left is messy & hard to draw, the diagram on the right is much cleaner.

The first thing we do is create an acetic acid solution by adding glacial acetic acid to water:
4 - Acetic Disassociated.jpeg
The water breaks the O-H bond in the acetic to form a positively charged Hydronium Ion [also called a Proton] and a negatively charged Acetate Ion.
Vinegar is usually a 5% acetic acid solution so this is already done for us in Marsofold's Tek.

When the Proton finds some DMT in solution it gloms on to the lone pair of the Nitrogen in the carbon tail, like your "buddy" from High School who only shows up when you've got weed. This gives us Protonated DMT which has a positively charged carbon tail:
5 - Protonated DMT.jpeg
But wait! Why doesn't the Proton glom on to the lone pair of the Nitrogen in the Indole ring? That Nitrogen has a 10π orbital---
*Record Scratch*
[Shut up Phin, you're over-complicating things]
*Record Scratch*
The Indole ring is big and strong and "protects" its Nitrogen from the Proton like a big brother on the playground.

Once the DMT has been Protonated that negatively charged Acetate ion comes in and sticks to the positively charged carbon tail like a magnet:
6 - DMT Acetate.jpeg
Which leaves us with DMT Acetate, a molecule that can withstand very high temperatures & wants to be in water.

So now, in our extraction, we have an acidic solution containing DMT acetate and a whole bunch of other Stuff. Lots of that other Stuff would rather be in Non-Polar solvents like naphtha, xylene, methylene chloride, etc, so we take a minute to mix our solution with some Non-Polar solvent and let the Stuff migrate over. That way we don't have to deal with it later and it doesn't dirty up our final product.

Sodium Hydroxide (lye) is an Ionic Molecule consisting of a positively charged Sodium Ion and negatively charged Hydroxide Ion that break apart completely when dissolved in water:
7 - NaOH Disassociated.jpeg

Now we're ready to convert our DMT Acetate back into the freebase. Adding an excessive amount of NaOH ensures that the equilibrium of the reaction favors the right side, the product. The first thing that happens is that the Sodium ion rips the acetate off to form Sodium Acetate and Protonated DMT again:
8 - Sodium Acetate.jpeg

And immediately thereafter the Hydroxide Ion grabs up that Proton to form water, leaving us with DMT freebase in solution.
9 - Freebase DMT.jpeg

That DMT freebase really doesn't want to be in the water so we extract it with naphtha and freeze it out to form a crystalline solid.
=====

This concludes your totally unnecessary Organic Chemistry lesson. As Shulgin said, "You may not understand it all, but you'll be able to hear the music."

Please ask any questions you might have, sorry for Nerding all over your thread.

Edited by Phineas_Carmichael, 05 April 2021 - 02:57 AM.

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#12 Norman

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Posted 05 April 2021 - 03:51 AM

Greatest. Shit. Ever.
I’ll be rereading that with my copy of Organic Chemistry for Dummies open beside me.
My lips moving the whole time.
Thanks Phin!
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#13 pharmer

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Posted 05 April 2021 - 02:43 PM

Thanks Phin.

 

and thank your parents for that expensive chemistry education we all get the benefit of :)


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#14 SlipperyJack

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Posted 05 April 2021 - 03:55 PM

Thank you so much for taking the time Phineas.

Largely over my head (as expected), but I will gratefully read it a few times and maybe a little bit of it will sink in.

 

Send me your address and I will mail you a brand new pack of fine-tipped Sharpies!


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#15 Phineas_Carmichael

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Posted 05 April 2021 - 11:52 PM

Thanks for the compliments, folks. Believe it or not my degree is actually in Biology. I would have gotten a Chem degree but that would have meant taking a 2nd semester of Calculus & it took me 3 tries to pass the first one! I noticed that 1 extra Organic course would buy me a Chem minor so I went for it, mostly so I could have another semester tinkering in the lab. I crash-landed in the Lecture portion with a 27% (the Curve adjusted it to a low C-) and a 98% in the Lab portion. Applied Chemistry is my strong suit.

Keeping all my Chem textbooks for "applied studies" like this was perhaps the best thing to come out of my Education. I'll be sure to tell Mr. & Mrs. Carmichael that my druggie friends on the internet sure appreciate their investment!

Funny enough Jack, the sharpies I used were from my lab coat. I usually use them to write temporary notes on the stainless steel surfaces in my lab at work so they don't need to be that fine. I made sure to stop by the office supplies cabinet today and pick up some fresh ones just in case.

The beauty of clandestine chemistry is that one doesn't really need to understand the nitty-gritty Chemistry to get great results. One really just needs to play around (safely!) in the Lab and find what works for them.

Edited by Phineas_Carmichael, 06 April 2021 - 02:32 AM.

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#16 TheObserver

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Posted 08 April 2021 - 10:43 PM

This is fascinating! Thank you for explaining it for us non chemists.
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