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2019 paper using hexane, ethyl acetate, and other solvents

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Loveall

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In the following paper (attached):

"Internet method for the extraction of N,N-dimethyltryptamine from Mimosa
hostilis roots"

the nexus STB process is evaluated with different solvents. Turns out that ehtyl acetate worked pretty well for extracting DMT (carrying ~6x as much DMT as hexane - see image below).

Has anyone used ethyl acetate with STB? It has been discussed, but haven't found any results on the nexus as far as I can find.

As mentioned in the first post of this thread, ethyl acetate is very efficient at extracting caffeine from whole beams after a steam treatment that opens up pores (commercial decaffeination process).

One path worth investing could be:

- Make an alkaline paste with rootbark/lime/water
- Microwave to open up pores (many not be needed, but could help more with larger bark pieces?)
- Extract with ethyl acetate
- Try to crystallize in freezer (it may not crash) or salt with an organic acid (e.g. citric).
- If salted, wash with fresh ethyl acetate and convert to FB. This process should be very clean/pure.
- Solvent should be easily reusable

Any thoughts on this? Has STB + ethyl acetate been tried before at the nexus (I searched but could not find any work on this)?

As I understand it, ethyl acetate is relatively low toxicity (~half the LD50 of Limonene) and used in the food industry (naturally occurs in low levels during fermentation). The human body can break small amounts of this solvent into ethanol and acetic acid without issues. Smell is pleasant to most people. It is available over the counter in many hardware stores where it has been replacing MEK as a less toxic and environmentally friendly alternative.

Disclaimer: I am partial to ethyl acetate because of several magical mescaline experiences and may not be very objective when it comes to this solvent.
 

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Thanks for tracking down the paper. It was referred to in a recent thread regarding using butanol.

I have to admit, the idea of using EA to extract DMT has crossed my mind as a result of your CIELO tek. I guess the next question might be, what else can it be used to extract?

We can be pretty confident that it'll do a good job using the method you've outlined - although I'd be very surprised if anything freeze precipitated using a normal freezer.
 
Thanks DFZ.

After posting I did a quick test. Couldn't help myself.

300g water, 25g lime.

Mixes in powdered MHRB. 100g at first, them 75g more (175g total to get a good consistency).

Paste looked good (turned a nice gray color) so I went straight to extracting (no microwave).

128g of ethyl acetate added, 46g recovered on first pull. Next pulls should be better recovery (near 100% I expect, ~75g absorbed by the paste to equilibrium is fine with be it it says at that number. The paste is loose and sandy, seems to be getting in the bark really well. Subjectively it works great so far.

46g of extract was cloudy, same look as naptha when it is loaded up. White stuff is crashing after a few minutes in the freezer.

I agree that a lot could remain in the solvent after freezing. I can add citric acid after the freeze precipitation is done to check how much still crashes as a salt. If reusing the solvent, it would be a one time penalty I guess. However, I think I'm also seeing ice xtals, that could be an issue, perhaps this time the solvent needs to be chemically dried before xtalizing.

So far looks very promising 🙂
 
Update: the appearance of ice made me ditch the attempt of FB precipitation.

I let the extract warm up and a water layer appeared. Decanted that off. Added 5mg/g of citric acid and massive milky clouds are forming.

Letting it rest now, will see if we get xtals.

It's only a few minutes of "work" to get to this stage 🙂
 
In that paper, they applied alkaline hydrolysis of the bark with sodium hydroxide for 2 weeks.
(btw. I did some test of the same method in the past and 2 weeks is too excessive, 3-5 days is enough)

Lime is not a very strong base and MHRB is quite woody material, but EA seems to be very good in penetrating processed plants, so it will probably works well.

Edit: Availability of EA is dependent on locality, unfortunately around here it's not easy to get.
 
I've come across this paper in the past and coming on the heals of the success of the CIELO tek, I was also curious as to whether ethyl acetate could be used to extract DMT.

From the paper:
"Finally, the major limitation of this work is the lack of purity assays of the extracts, due to law restrictions in Brazil regarding the possession of isolated/purified DMT."

So what does that mean? What is being reported on in Table 2?

Also, the researchers tested hexane. How does that yield generally compare to heptane and naphtha?
 
Update: Cloud after adding citric acid precipitates as what looks like honey (see image below).

Turns out that honey is what DMT citrate looks like according to this post dmt citrate chemistry - Advanced/Enhanced chemistry - Welcome to the DMT-Nexus

So next time will use fumarate to get xtals.

The solution was still alkaline (based on pH paper) and more citric acid was needed to make it acidic. There should be over a gram of DMT in the 1st short pull based on rough titration.

@shroombee: not sure how to answer all your questions. A reference is good to check for purity analytically (see how well it matches in the instrument). In the old days they would mix the product with the reference and scan with heat, see if they got a single or double melting peak. Essentially, with the standard in hand you run it through the same test and you don't need to worry about absolute calibration.
 

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Loveall said:
A reference is good to check for purity analytically (see how well it matches in the instrument). In the old days they would mix the product with the reference and scan with heat, see if they got a single or double melting peak. Essentially, with the standard in hand you run it through the same test and you don't need to worry about absolute calibration.
Oh is that what they mean by the lack of purity assays? Meaning they technically don't have a pure sample to use as a reference. I thought there was some implication that the values reported in Table 2 might be inaccurate. But that isn't necessarily the case.

Just ordered some fumaric acid. Looking forward to running these experiments. :)
 
Loveall - you're always so quick!

It looks like DMT citrate is pulling water out of the EA with it, which is to be expected. It will be good to see what the fumarate does but it's also fair to anticipate that it might behave similarly to the citrate. Fumarate syrup does crystallise after standing for a few days after the solvent has been removed - I wonder if your citrates might do this as well?
 
Dumping these potentially useful references here:

Water-enhanced solubility of carboxylic acids in organic solvents and its application to extraction processes (Solubility of fumaric acid in some solvents including butyl acetate - but not ethyl acetate.)

Descriptors for the α,ω-dicarboxylic acids from oxalic acid to sebacic acid. (Gives solubility of succinic acid in a variety of solvents.)

Here's a hint why DMT salts with carboxylic acids might tend to be gooey:
The formation of room-temperature liquid eutectics is favored by the mixing of a hydrogen-bond acceptor (e.g., a quaternary ammonium salt) with a strong hydrogen-bond donor (e.g., a carboxylic acid).
(In C.F.Poole, "Liquid-Phase Extraction" Chapter 2 - Solvent Selection for Liquid-Phase Extraction, section 2.5.4 Deep Eutectic Solvents.)
 
downwardsfromzero said:
Loveall - you're always so quick!

It looks like DMT citrate is pulling water out of the EA with it, which is to be expected. It will be good to see what the fumarate does but it's also fair to anticipate that it might behave similarly to the citrate. Fumarate syrup does crystallise after standing for a few days after the solvent has been removed - I wonder if your citrates might do this as well?


This is exactly what happened. Fumaric started to crash as what seemed like xtlas but quickly turned into a golden honey, just like citric. Excellent prediction DWFZ.

Maybe this could be useful for conversion? I think I'm gonna try to decant, add naptha, then add sodium carbonate. Hoping the sodium carbonate reacts with the watery citrate/fumarate and releases DMT FB into naphtha (?).

Will give it a try see what happens...
 
downwardsfromzero said:
Fumarate syrup does crystallise after standing for a few days after the solvent has been removed
Loveall said:
Maybe this could be useful for conversion? I think I'm gonna try to decant, add naptha, then add sodium carbonate. Hoping the sodium carbonate reacts with the watery citrate/fumarate and releases DMT FB into naphtha (?)
Could you decant and let the remaining solvent evaporate? Then see if the fumarate xtalizes after a few days?
 
shroombee said:
downwardsfromzero said:
Fumarate syrup does crystallise after standing for a few days after the solvent has been removed
Loveall said:
Maybe this could be useful for conversion? I think I'm gonna try to decant, add naptha, then add sodium carbonate. Hoping the sodium carbonate reacts with the watery citrate/fumarate and releases DMT FB into naphtha (?)
Could you decant and let the remaining solvent evaporate? Then see if the fumarate xtalizes after a few days?
Unfortunately I've already started converting the oils to FB.
 
Got the oil that precipitates form the ethyl acetate extract to convert to beautiful white FB.

Simply decanted, rinsed once with naphtha added sodium carbonate and a few drops of water. Bubbles and loose excess sodium carbonate formed as the honey broke down. The naphtha was decanted and put in the freezer where white crystals formed.

However, the paste is absorbing too much ethyl acetate. Currently the process is not practical I would say. Going to try NaOH see if that releases the solvent. In the paper above, it was mentioned that NaOH worked well.

So a possible process would be STB paste with NaOH, ethyl acetate extraction, crash DMT oil (e.g. with citrate), decant, cover with naptha, react oil with sodium carbonate and some water (water ends up being absorbed with more sodium carbonate addition), decant, freeze, decant.

Not necessarily practical unless there is a big step up in yield. Purity looks good from what made it through. However, it may be better to simply extract with Naphtha to begin with (~Lazykan's TEK).
 
Tested again. This time I used sodium carbonate (200g water, 30g Na2CO3, 100g bark) and steamed off 100g of water in the microwave. I let ethyl acetate extract by diffusion (like with coffee beans), based on pH paper something alkaline is being absorbed over time.

This time I dried the extract with anhydrous CaCl2 before salting. Some gunk precipitated at this step.

Split and salted dry extract two ways:
- Citric acid. Pink gunk crashes with some crystalinity to it.
- Fumaric acid. White xtals crash.

So fumaric acid is the way to go to get loose xtals.

Right now this approach seems like a curiosity (STB + naphtha is simpler since conversion to FB is not needed). If ethyl acetate yields more with less work (because it penetrates the steamed bark better) that conclusion could change. Also, if DMT fumarate is the desired final product, this process could be less work (no need to manage a FASA jar, just drop in fumaric acid into the chemically dried ethyl acetate).

It is interesting how different the DMT citrate and fumarate salts behave in ethyl acetate. I wonder why/how the citric acid addition has a pink precipitate.
 
Thanks for the updates. I like the food-safe aspect of the tek (at least up to using naphtha to convert to freebase). Especially since a lot of the videos out there that explain how to extract DMT using lye don't include enough safety recommendations (IMO).

I'm also partial at this time to oral pharmahuasca so I don't need freebase DMT.
 
Good progress, well done.
Loveall said:
I wonder why/how the citric acid addition has a pink precipitate.
Probably something to do with the ionic charges on the coloured material that is dissolved, suspended or held colloidally in the EA. It goes pink because of the acid, in the solution it will have contributed to that greenish cast there appears to be. It doesn't come out with the fumaric acid, so maybe either the hydroxy group of the citric acid pulls it along, or perhaps it's the tribasic nature of citric that makes the difference whereas fumaric acid 'locks' quite snugly between two DMT molecules, leaving the pink/green stuff untouched.

Citric acid is as well more bulky in comparison with the essentially planar fumarate ion - bits of it could poke out and stick onto other stuff - and then there's the possibility of the intramolecular hydrogen bonding playing a role in this by reserving that portion of the molecule for a chelating effect, which is essentially a combination of the hydroxy group and the third carboxy group mentioned above. It would be interesting to check the stoichiometry of the DMT citrate in view of this.
 
DWFZ, I think your "chelating" suggestion is spot on.

The citric salting is clearing up a lot quicker and precipitate is pink.

Fumaric is still crashing, but some pink had appeared at the edges of the jar among the whiter xtals.

So, there is this pink stuff that is present in the dried ethyl acetate extract from bark. Citric acid crashes it all quickly, but Fumaric is slower (slow enough that DMT xtals precipitated first).

Also, yields are not very good.

I can't get the ethyl acetate approach to work well for bark/DMT. A STB naphtha TEK such as Lazyman's process is much better from what I can tell.
 
I'm going to work on this more. Reason is because the dmt citrate honey obtained in post #7 when lime was used to base should be soluble in PG/VG and vapable. Solvent loss was a problem, but going to lower water concentration has solved that issue (85% recovery in first pull and 95 to 100% recovery in subsequent pulls).

Here is what I'm gonna try:

- 1:1.5:0.25 finely powdered MHRB:water:lime
- EA pulls (~5 x 1.5)
- Settle combined coffe filtered pulls in fridge until clear and decant
- Salt with citric acid (~0.05) and allow oil to settle
- Decant and rinse with fesh EA
- Air dry
- Dissolve dmt citrate oil candidate in ~2 to 3 parts PG/VG

This may be a quick way to make e-juice for vaping. For me, making a quality e-juive is cumbersome because the DMT needs to be very clean to avoid clogged atomizer coils. Extra purification steps are needed compared to direct heat vaporizing methods (at least for me).
 
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