TEK Ethyl acetate approach [CIELO]

[doubledog]

On the other hand, ethyl acetate is a polar solvent, miscible with water to some degree. Its use in decaffeinization of coffee also suggest that it could penetrate dry plant matter (at least I assume that this process needs dry coffee beans, I really don't know)

There are a few methods to decaffeinate coffee beans. They all use water or steam somewhere in the process. With direct ethyl acetate extraction, beans are first steamed and then soaked in the ethyl acetate to remove the caffeine.

How is decaffeinated coffee made? The chemistry of coffee decaffeination

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www.compoundchem.com

Thank for clarification, shroombee. So it seems that some water is really needed.

Another useful information is that mescaline freebase can be extracted from dry cactus powder using ethanol. Maybe EA behaves more like ethanol, than like limonene.

Does ethanol work on dry power because we're using 70% ethanol and thus there is quite a bit of water present?

I meant extraction of mescaline in form of freebase by using alkaline ethanol, not typical maceration of dry cactus powder in 70-90% (acidic) ethanol.

 

[Loveall]

One idea is to dry the paste enough with CaCl2 so it can be ground in a blender to fine particles again. That should do it. Limonene was not good at pulling dry paste for me, but maybe ethyl acetate is different

Loveall, this would be interesting to find out.
Issues with limonene pulling dry basified cactus are not surprising, considering non polar (lipophilic) nature of limonene. It was discussed on the forum somewhere that even two-phase liquid-liquid extraction is tricky with limonene, as it is difficult to mix it with water properly.

On the other hand, ethyl acetate is a polar solvent, miscible with water to some degree. Its use in decaffeinization of coffee also suggest that it could penetrate dry plant matter (at least I assume that this process needs dry coffee beans, I really don't know)

Another useful information is that mescaline freebase can be extracted from dry cactus powder using ethanol. Maybe EA behaves more like ethanol, than like limonene.

Makes sense. In someblackguy's original work, the lime paste was dried completely and actives where indeed extracted with ethyl acetate based on his bioassay. Ethyl acetate was evaporated (not salted) leaving an oil behind. So drying the paste should work (?). His result was a green extract, so maybe microwaving to partially dry + extracting at 0F is more robust because the extract is near colorless.

One interesting thing about the microwave (which I think you don't have) is that we may be doing something called Microwave Assisted Saponification (MAS).I believe it breaks down esters (generally soluble in ethyl acetate which is itself an ester) into carboxylate ions and organic alcohols. An important example is,

Chlorophyll + 2OH- ⇒ Chlorophyllin-- + Phytol + Ethanol
​

So less matter is soluble in ethyl acetate. In the example above, assuming ethanol mostly evaporates, only phytol is available for ethyl acetate to pick up. It has an amber color (apparently) and when extraction at 0F it does not appear to be picked up (since extract is colorless).

 

[doubledog]

It turns out that really important thing in every mescaline extraction is how to NOT extract some compounds.
Microwaving and low temperature apparently help with this in case of EA.

Main hassle in the extraction with alkaline ethanol is this green chlorophyll fraction. It's really nasty stuff.

 

[shroombee]

In someblackguy's original work, the lime paste was dried completely and actives where indeed extracted with ethyl acetate based on his bioassay. Ethyl acetate was evaporated (not salted) leaving an oil behind. So drying the paste should work (?). His result was a green extract, so maybe microwaving to partially dry + extracting at 0F is more robust because the extract is near colorless.

Reviewing someblackguy's thread, he doesn't say how long he pulled with ethyl acetate. I'm guessing it was a lot longer than the pull times we're currently working with.

Short pulls from dried paste might be more colorless?

 

[Loveall]

It turns out that really important thing in every mescaline extraction is how to NOT extract some compounds.
Microwaving and low temperature apparently help with this in case of EA.

Main hassle in the extraction with alkaline ethanol is this green chlorophyll fraction. It's really nasty stuff.

I agree. I think chlorophyll itself and maybe other plant stuff interacts with mescaline in solution and makes it more difficult to crystalize.

Whatever the reason, microwave + quick 0F cold extraction seem to make a very clean extract (near colorless) that xtalizes well experimentally. I think I may get an insulating liner for my making jar

The nice thing about ethyl acetate is that if you overloaded with citric acid and/or give it enough time, mescaline citrate does xtalize, even for the dirtier extracts (room temp and whole plant). Not the prettiest xtals, but active as we have seen so far.

Putting it all together (microwave saponification + cold short extractions + citric acid excess), seems like the process could be robust and give needle xtals in general/reliably.

 

[Loveall]

It turns out that really important thing in every mescaline extraction is how to NOT extract some compounds.
Microwaving and low temperature apparently help with this in case of EA.

Main hassle in the extraction with alkaline ethanol is this green chlorophyll fraction. It's really nasty stuff.

I agree. I think chlorophyll itself and maybe other plant stuff interacts with mescaline in solution and makes it more difficult to crystalize.

Whatever the reason, microwave + quick 0F cold extraction seem to make a very clean extract (near colorless) that xtalizes well experimentally. I think I may get an insulating liner for my making jar

The nice thing about ethyl acetate is that if you overloaded with citric acid and/or give it enough time, mescaline citrate does xtalize, even for the dirtier extracts (room temp and whole plant). Not the prettiest xtals, but active as we have seen so far.

Putting it all together (microwave saponification + cold short extractions + citric acid excess), seems like the process could be robust and give needle xtals in general/reliably.

Yep, and cold 0F extraction even more so. Could be very clean extracting chilled and without water. Or microwaved+dry+chilled. Question is do we need to fully dry? We got some colorless extract already without fully drying. However, fully dry powder could be better, I don't know. Tests are needed to know.

It may be worth to make the paste, microwave to remove 100g, dry the rest in the oven at low temp, grind to a fine powder, bring powder to 0F, extract with 0F fresh ethyl acetate quick pulls. That should be very clean I think (all in). Wonder what yield would be...

 

[doubledog]

I think I may get an insulating liner for my making jar

The nice thing about ethyl acetate is that if you overloaded with citric acid and/or give it enough time, mescaline citrate does xtalize, even for the dirtier extracts (room temp and whole plant). Not the prettiest xtals, but active as we have seen so far.

Putting it all together (microwave saponification + cold short extractions + citric acid excess), seems like the process could be robust and give needle xtals in general/reliably.

You should be awarded with Honorary Insulating Liner from Nexus members :d
Really great method :thumb_up:

Xtals from not super clean extract could be easily cleaned or recrystalized.

 

[Loveall]

Update to post #286/289

Crystals where large and white (some ~ clusters 8mm in diameter - see second image with scale in mm). Product was white straight out of the extract and did not need a wash.

Yield was low, 0.6% (1 to 1.2% is reference for this material). Not surprising because the paste congealed after adding NaCl. I kept the paste and plan to recover the yield with longer room temp pulls that will need extra citric to xtalize and washes.

Next will try the same technique (MAS + 0F quick extractions), but replacing NaCl with CaCl2. No congealing is expected, so hoping for white xtals with high yield of the 0F extractions are efficient.

When I combined this product with the previous extractions the difference in color became apparent (see 3rd image, MAS+0F is towards the top).

 

[merkin]

Quick update: Added total of 18g Citric acid. The solvent cleared up completely (not color, just clarity). Very little precipitation a day later (a small amnt of gold-ish goo). After decanting there was some stickiness and something on sides. Dissolved in 30ml hot water as suggested to clean bottle sides, evaporating that now. Otherwise pretty much nothing except two blobs of the gold/brown goo in filter paper.

I guess either my source material is no longer much good or I got the pulls wrong somehow. But going over notes I cant see, but then the pulls kinda took all my attention and I only made notes afterwards.

Have more of the powder so I will try again. Bit disappointing but seeing the crystals above keeps me excited! I will start the harvest process with some pedros and bridges I have in the hope that that improves things!

 

[Loveall]

Quick update: Added total of 18g Citric acid. The solvent cleared up completely (not color, just clarity). Very little precipitation a day later (a small amnt of gold-ish goo). After decanting there was some stickiness and something on sides. Dissolved in 30ml hot water as suggested to clean bottle sides, evaporating that now. Otherwise pretty much nothing except two blobs of the gold/brown goo in filter paper.

I guess either my source material is no longer much good or I got the pulls wrong somehow. But going over notes I cant see, but then the pulls kinda took all my attention and I only made notes afterwards.

Have more of the powder so I will try again. Bit disappointing but seeing the crystals above keeps me excited! I will start the harvest process with some pedros and bridges I have in the hope that that improves things!

Let's see what yield you get from the 30ml evap and blobs. Usually we wash the walls with ethyl acetate before dissolving in water to recover, not sure if you did that.

Do you still have the source cacti? You can try a warm pull on that and see if it still giving clouds and precipitation.

I don't think dry cacti powder goes bad over time, but not sure.

One very important thing is to make sure there are no droplets or debris in the extract before salting. Something I always check (and you may have done that already).

 

[starway7]

your crystals look good..but have you tryed them yet?

years back..i used the ...[simple three step mescaline citrate] method i posted above...

And once after letting a fan evaporating all night,,,[in the morning]... i had a nice amount of white beautyfull crystals in the evaporation dish!

...But i wasnt shure those crystals were mescaline!

I taste tested.. some on my toung..and it burnt or stung my toung...


and ... [because i used a lot of lye and citric acid]... i was afraid it was just citric acid crystals.. or even lye crystals?!

I threw it away...but maybe i shouldent have?

I believe i remember it said mescaline crystals should be quite Bitter !...if put on toung...

but should not sting or burn the toung...

It felt like it was stinging my toung and i wasnt shure of its purity!

there is sooo much goo and slime in cactus it was so much work ..and that smelly exylene!

It takes a lot of work to extract it right!

 

[Loveall]

starway7, multiple bioassays from our approach here from myself and close personal friends, plus Metta-Morpheus and shroombee - have worked as expected. On top of that we have the GC-MS analytical result from Benz, the clouds that crash are mescaline citrate.

When it comes to the extraction you screenshot, I think you are referring to the method someone posted on the shroomery. I read it a while ago, going off memory it is a base lye extraction with xylene salted with aqueous citric acid, and evaporated. The water salting isn't titrated, so there will be mescaline citrate but also a bunch of excess citric acid (that may have been what stung your tongue). I don't think it is a proper process because of the random over titration. If using xylene, Kash's extraction seems like a good process to me.

 

[Loveall]

Update on the congealed sodium pastes with low yields (one using Na2CO3-0.7% and one using NaCl-0.6%).

Yields recovered (back to 1%) by doing long warm extractions on the congealed paste. Product was more difficult to xtalize and crash (was sticking to the walls, had off colors, etc) and ended up having a slight tan color that did not wash off.

I've started the MAS (microwave assisted saponification) + quick 0°F (using CaCl2 to avoid ice) extraction. I have a silicone coozy for the mason jar . Will report on this later this year, hoping for:

- Near colorless extract with very little plant matter thanks to microwave breakdown/saponification and low temperature
- Good yield (1%) - thanks to calcium making cacti in ethyl acetate sandy (large surface area)
- Robust process to different starting cactus material giving large white crystals
- Solvent reusable many times

 

[Loveall]

Results from MAS + CaCl2 + chilling both paste and solvent to ~0°F

Paste was not very loose/sandy unfortunately. Yields was 0.75%. Will do a messier pull to recover the last 0.25%.

So far the process in the published TEK is gives the best result, but the extract is green (trying to keep it more colorless for increased robustness and less sensitivity to plant matter).

So, next I'm testing a version of what doubledog highlighted (full dry)

- 300g water/25g lime/100g cactus powder past
- Complete dry in microwave. This was pretty easy with a shallow baking dish. Was 17 minutes of 1000W irradiation with several stirrings in between. Was less than 30 minutes of work. Paste went from clumpy to smooth/wet to clumpy again
- Run dry alkaline paste through blender again to maximize surface area
- 0°F extraction 60s x 5 (both solvent and powder are chilled in freezer first)

I'll update with yields. This is similar to ACY's process but with no chemical drying agent and with ethyl acetate instead of acetone.

 

[doubledog]

I think this is the tek mentioned:

Easy Three Step Mescaline Citrate - The Psychedelic Experience - Shroomery Message Board

and it's quite interesting for us, because it involves crystalization of mescaline citrate from cold water at the end.
Without that step it produces mescaline citrate mixed with citric acid and maybe some sodium citrate.

 

[Loveall]

Results from MAS + CaCl2 + chilling both paste and solvent to ~0°F

Paste was not very loose/sandy unfortunately. Yields was 0.75%. Will do a messier pull to recover the last 0.25%.

So far the process in the published TEK is gives the best result, but the extract is green (trying to keep it more colorless for increased robustness and less sensitivity to plant matter).

So, next I'm testing a version of what doubledog highlighted (full dry)

- 300g water/25g lime/100g cactus powder past
- Complete dry in microwave. This was pretty easy with a shallow baking dish. Was 17 minutes of 1000W irradiation with several stirrings in between. Was less than 30 minutes of work. Paste went from clumpy to smooth/wet to clumpy again
- Run dry alkaline paste through blender again to maximize surface area
- 0°F extraction 60s x 5 (both solvent and powder are chilled in freezer first)

I'll update with yields. This is similar to ACY's process but with no chemical drying agent and with ethyl acetate instead of acetone.

Update: full dry does not work for me. The extract is cloudy and unfilterable - a mess. Fortunately, adding 100g of water to the paste clears up the ehtyl acetate very quickly making the process easy. The paste was nice and sandy after adding the water, expecting good yields. Thick clouds forming now, expect to measure xtal weight tomorrow.

The published TEK remains the best approach. I am going to try the microwave process, stopping when the paste becomes sandy (but still wet). That may be the only way I can think of making the current process more robust and still having a sandy moist paste that is not loaded with ethyl acetate soluble chlorophyll (which is the ideal situation as far as I have seen experimentally).

 

[shroombee]

I am going to try the microwave process, stopping when the paste becomes sandy (but still wet).

What do you mean by sandy? How does sandy compare to my photos here? I describe this texture as moist fluffy/crumbly.

 

[Loveall]

I am going to try the microwave process, stopping when the paste becomes sandy (but still wet).

What do you mean by sandy? How does sandy compare to my photos here? I describe this texture as moist fluffy/crumbly.

Yes, your pictures look sandy. What you call loose, I call sandy. That gives the best yields for me.

This is what I'm seeing/thinking,

- Raw paste (300g water) nice and sandy, good yield for you and me, but a lot of green plant matter comes with the pulls. Some people have issues with fast/easy xtalization. This is the current published tek.
- Microwave paste A (200g water, 100g water evaporated): No green super cleaner extract, should be more robust in general for xtalization, bit yields are 30% depressed because paste is not as loose (sandy).
- Microwave paste B (100g water, 200g evaporated): Paste is loose/sandy again. Best of both worlds (high yield, less plant matter, more robust)? -> I'm testing this next
- Microwave paste C (0g water, 300g evaporated): Ethyl acetate is a mess (cloudy unfilterable). Does not work. Had to add 100g of water (reconstitute what would be Microwave paste B?) to get things to work again.

Pulling with chilled (0°F) ethyl acetate for all of these.

Hope the current work makes sense. Published TEK works for me every time, but want to make something more robust that is less sensitive to different kind of cacti material.

Cheers

 

[merkin]

Let's see what yield you get from the 30ml evap and blobs. Usually we wash the walls with ethyl acetate before dissolving in water to recover, not sure if you did that.

Do you still have the source cacti? You can try a warm pull on that and see if it still giving clouds and precipitation.

I don't think dry cacti powder goes bad over time, but not sure.

One very important thing is to make sure there are no droplets or debris in the extract before salting. Something I always check (and you may have done that already).

Thanks Loveall, the water is still evaporating! Don't hold much hope for any crystals tho. Yes I did swirl/wash with room temp ethyl actetate before the water. Honestly there was negligable residue on the sides of the lower end.

Unfortunately I dried and then discarded the source cactus mix into the compost heap already. But I have almost a half kilo left to play with before I start harvesting my own plants, something that's very difficult to contemplate! So many years of nurture, but then...why else? I am getting more ethyl acetate tomorrow as I only had around a litre of lab sourced. Had to buy a minimum 25l so thankfully its not that expensive! Might be a bit more 'industrial' than the EA I used before. We don't have such products in hardware stores here. But the chemstore AR version is literally 10x the price.

As for 'no droplets or debris' I fear I might have blown right through that stop street. I did have to decant the entire pull once due to some stuff on the bottom but didn't note at what point. Maybe this is where it went wrong. I was a little unsettled doing the pulls, stirring and trying to keep everything frosty freezing and around a minute I probably rushed things a little? Do you recommend filtering the raw extraction liquid?

@shroombee -
Would you please elaborate how you go about the salting with the acid using the stirrer? I have one. I maybe got a bit literal on the 'allow crystalization to complete undisturbed' part of the tek.

Anyway, I look forward to trying again. Really keen to see those crystals! Reminds me of a rue Manske but with green instead of gold.

Here's the bunch of pedros that need a little thinning, especially the large group. I planted three way too close to each other, but who knew they would get so big when you're just dealing with little cuttings

 

[shroombee]

@Shroombee - Would you please elaborate how you go about the salting with the acid using the stirrer?

Sure. I put the beaker on the magnetic stirrer and get the stir bar spinning at the fastest speed where droplets of solvent don't splash out of the beaker. Using a beaker size in which the beaker is half full with solvent seems to work best to reduce splashing. I put an upside down paper bowl over the top for safe measure. There should be a nice vortex in the middle of the solvent.

Weigh out your citric acid - from 5 mg/gram up to 20 mg/gram (mg of citric per gram of solvent). Then dump it all into the beaker. The solvent should immediately turn cloudy and you won't be able to see the vortex. You should notice many grains of citric acid sliding around the bottom edge of the beaker. Within 60 seconds you might notice xtals that look like snow spinning within the solvent. It can be hard to see when they start appearing because the solvent will still be cloudy.

Within maybe 3 minutes the solvent will clear up enough that you can see the vortex and most of the citric grains should be dissolved, replaced by xtals. A flashlight helps to see the vortex. You might think all that snow spinning around is citric acid grains, but nope - they're xtals.

If you stop the stirrer at this point you'll see snowy xtals continuing to swirl around the solvent. They will settle to the bottom of the beaker within a couple minutes and the solvent will be clear, indicating to me that xtalization is complete. I like to run the stirrer for a total of 5 minutes for good measure.

Edit: I run the stirrer a total of 10 minutes, which is probably overkill.

Optionally, after 5 minutes, you can knock xtals off the walls by carefully manipulating the beaker so that the spinning stir bar and vortex gets close to the walls.

BTW, I haven't done rigorous A/B testing, but it may be more reliable to bomb with citric and aggressively stir right after the pulls, rather than waiting around or using slow diffusion. Bombing with aggressive stirring is when I've gotten my best yields. But there might be other factors involved and I'll have to do some A/B tests to know for sure.

Regarding how much citric acid to use: We believe 5 mg/gram works fine if the extract is relatively clean of plant material. 20 mg/gram may be necessary to force xtalization when there is more plant material interfering. You can try lower amounts and increase if necessary. I've done A/B tests with different amounts of citric and yields are the same (assuming full xtalization). Lower amounts of citric produce larger, fluffier xtals that stick to the walls but are easy to catch in a coffee filter. Higher amounts of citric produce small xtals that don't stick to the walls, but a negligible amount of xtals will slip through the coffee filter.

I also recommend running 50 gram batches of dried cactus rather than the typical 100 grams, until you get a repeatable process. Just to conserve your precious material.

Hope that helps. Good luck!