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NO HEAT Canola oil, Na2CO3 and vinegar extraction

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I'm unsure why vegetable oil was abandoned as a solvent by this community however there has been a recent push to use more green solvents. Vegetable oil to extract alkaloids has been mentioned in a older patents EP2475374A2 and KR20120093862A. This is the most accessible method of extraction and it seems.

Sodium carbonate saturated solution is alkaline (12.1 ph) enough for mescaline and vegetable oil is much easier to access then many other non-polar solvents people use. I needed to do a few clean up and separation of the oil layer but I don't have any glassware and did a complete noob/hobbyist extraction

There is a thread on DMT-nexus that shows mescaline acetate as soluble in isopropanol however I question if that is correct. I am not chemistry inclined so I may be wrong. However a paper shows that sodium acetate is almost insoluble in 1-propanol and 2-propanol is almost identical in properties just more toxic. Even at 30% water/1-propanol ratio sodium acetate is almost completely insoluble. So why would mescaline acetate be any different. Unfortunately I when trying to boil my isopropanol to dissolve the precipitate like people do with MEK I ended up losing 90% of my product in the waterbath so I'm unable to verify if I'm right this time. (too much to evaporate for only 300mg)

I'm sure this would also work with DMT acetate. In a old thread people mentioned losses due to dry root absorbing the oil however with a liquid to liquid extraction rather than a solid/liquid like what was attempted in the past this may might resolve that issue.

Steps to extracting Mescaline acetate.
1. Powder dry outer flesh of cacti.
If you want to use whole cactus I'd suggest a boil of the bulk material before and reducing the volume until a manageable volume of perhaps 50-100ml

2. Add a saturated sodium carbonate solution to the dry flesh 2x the volume.

3. Add the vegetable oil of your choice I'd suggest an oil high in omega 9. Sunflower oil was used in the past but choose high oleic sunflower oil. The properties seem to differ between the oils there are a few papers that go deeper into this. Olive oil is also good but more expensive. I choose canola oil since rapeseed soil isn't available here. canola is made from modified rapeseed soil.

4. I didn't use any heat so I followed the patents which say 30hours soak with mixing the two layers. I mixed every couple hours for 2 days at 20C. If heated this could be reduced to 1 hour to pull.

I did 2 pulls of oil which I believe is enough but if you want do as much as you'd like.

5. After separating the non-polar layer from the alkaline aqueous layer. I added a acidic aqueous layer to salt and pull the free alkaloids that should be in the non-polar.

I used 1-1 volume and did this step twice. I used white vinegar at 5%. Lower would likely have pulled less extra impurities but I didn't have ph paper.

6. I now have a acidic aqueous layer which is vinegar at 5%. I evaporated this and ended up with a goo after it sat for a while. which weighed 472mg

7. From here I placed the goo into a small glass vessel and placed cold 70% isopropanol and a precipitate formed. I rewashed the precipitate with fresh iso 5 times until it was a much lighter color. I collected the isoproponal washes and when dried weighs 134mg which I believe are mostly impurities/carbohydrates.

I messed up here and tried heating the isopropanol to attempt to dissolve the precipitate like I've read with MEK however the wax I used to close the glass dropped melted and I lost 90% of my product.

I don't have reagent to test the remaining material and it isn't enough for an allergy test so I'll need to reattempt this in the future and with more dry material.

This took me 2 weeks but used zero heat only at the end to evaporate final products I used open flame.


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as a general guide, two factors are considered when performing the A/B process on common alkaloids: pKa and logP. The former is relevant to selecting the optimal acids and bases for the extraction, the latter for the solvent selection. Vegetable oils may fit in the latter, but they can be quite messy because of base hydrolysis (saponification). Limonene is the commonly used green solvent for mescaline, it is effective and relatively clean.

tips (for compounds with a single pKa): taking a pH 2 units below the pKa, results in >99% salts in solution. Taking it to 2 units above, >99% free base.

The lower the logP (sometimes it goes into the negative), the more polar the molecule. Search solvents for logP as well; the more similar they are to the alkaloid, the more soluble.

Pubchem is a great resource for finding those factors; see 3.2.6 and 3.2.8.
At saturated sodium carbonate solution I didn't notice any saponification but it is limited to the 12.1 pH cap. Limonene I'm sure is a better solvent however not as readily available although not too difficult to obtain. I personally don't care much about being green over being accessible. Overseas prices are quite larger factor than in the states price difference being 5-10x between the two. Not a huge difference considering you can reuse d-limo a few times where as the oil might go rancid sooner.

I did need to clean up a few times however mostly due to lack of proper sized glassware and separation vessel. I ended up using thick straws for better separation.
Do you have any information about mescaline acetate solubility in isopropanol? The page on mescaline shows it is soluble but why would sodium acetate be so different?

Sodium acetate is almost insoluble in 1-propanol and 2-propanol is basically the same.


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The mescaline acetate salt is soluble in isopropanol because mescaline is amphipathic (has nonpolar and polar moieties); it has four proton-acceptors (the three methoxys and the amine), one donor (the amine). All of those interact with the H on the OH-group of isopropanol. The isopropyl part of isopropanol interacts with the carbon-carbon bonds of the rest of the mescaline molecule by what is known as Van Der Waal's interactions. Those interactions are also present with the acetate counterion, but for sodium acetate, the ionic interaction with sodium is stronger.

Solubility would need to be determined experimentally.
You can also think of it like that:

When introducing a charge to an organic molecule changes are much higher, that it still dissolves in a very polar organic solvent (like alcohols = IPA). Vice versa if you introduce a charge onto a metal it will most likely be not solubly (still maybe depending on counter-anion though).

Reason is you could speak of Na+ as a very *naked ion*, with its charge very much exposed to its chemical surrounding. But on the other hand an organic molecule will most likely be bigger, but in total just carry the same charge (physically all charges have the same magnitude). This furthermore could be even more reduced by some mesomery of the organic molecule, which will decrease the *overal felt charge strength* even more.

That is why Na+ -OAc will most likely not dissolve in IPA. The ion is to hard to stabilize because of its strong *felt charge*.

Now you could make some playing around by increasing the metal ion's size in a mind game. You would go from Na+ to K+ and still have the same charge, but on a bigger volume. Now for example K+ -OH is just a little bit soluble in IPA, while Na+ -OH would not. So Alkaloid+ -OAc is just a more extreme example when comparing.

In general Alkaloid salts pretty often dissolve in Alcohols like IPA when heated as much as possible. That is why these are used to recrystallize their salts, but it is always a wasteful process as you end up losing more like DMT-rex in petrol-ether-like stuff.
So I read up on what was mentioned here but then what do you suspect is the precipitate that forms upon adding the isopropanol?

It's a solid without a doubt and is soluble in vinegar. I considered that isopropyl acetate formed but after more research requires a strong acid to actually form and not just mixing acetate and iso.
I considered it was DNA but even without cold temps it falls out of solution and is not 'stringy' like I've seen DNA extractions. With cold isopropanol more salts are said to precipitate so still returns to my idea that it is mescaline acetate?

Judging purely on the weight removed since I lost the actual precipitate due to human error it matches what I'd expect the mescaline acetate to weigh. (300-350mg) I removed the colored isopropanol a few times so I could test if that has any activity. I still have 130mg which I assume are impurities from the goo. Since mescaline acetate should have dissolved in the isopropanol that should be where the acetate is right?

BTW even if it is soluble would the fact that I'm using only 2mL of isopropanol help my case? I'm not saying its completely insoluble so perhaps the isopropanol is saturated and the remaining has crashed out? I would have zero issue doing an 'allergy' test on both however amounts are too small to have any noticeable effects. I'll need to reattempt this next time with more dry material.

I'll be reattempting this procedure in the future and hope to actually test with tlc but the plates are more expensive than I thought.


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So I'm actually quite interested in this and would love to find a possible explanation.

Is it possible that since I washed and dried the acetate in 5% vinegar that makes the mescaline acetate protonated since pkb is 4.44 so at 2.4 ph 99% should be protonated.

So when adding the isopropanol it accepts the extra h and forms Isopropyl oxonium ion? doesn't react to the H on the mescaline acetate causing it to crash out of solution? IDK how oxonium ion react normally makes sense that it wouldn't just return the H+.

Found a few new terms like electrophiles and carbocation so idk if a weak acid like vinegar can do the same as hcl but following the ph alone and pkb of mescaline I think this is plausible explanation.

Please correct me and give your possible explainations whenever you have the free time.
Several things are unclear to me about your method. Was the "vinegar at 5%" 5% acetic acid, or 5mL vinegar diluted with water to make 100mL?
Was the vinegar clear and colourless? What about the canola oil? How clear did that look?
When you say, "washed and dried the acetate in 5% vinegar", what did you do with the solids, and with the solution?

Mescaline acetate, by the way, already has the mescaline protonated. The mescaline is only unprotonated at higher, basic pH.
[It may be the case that sodium carbonate is simply not strong enough to do this deprotonation very effectively, and that you need to do a lot more pulls on the cactus material to get a significant recovery of alkaloids.]
Acetate anions can, however, combine with a further equivalent of acetic acid to form a biacetate anion. Not sure if mescaline biacetate would be particularly stable, but sodium biacetate is used as a vinegar flavouring in crisps/potato chips. How does your product smell once all the IPA has evaporated?

And do you know if the cactus that you used is even active?

All in all, it would be helpful if you could re-write your extraction/purification procedures with as much precise detail as possible. And remember - rule zero of extracting is never to throw anything away until you're sure you've got the goods.

Your precipitate on adding IPA might be protein or pectin, or sodium acetate. You could look into doing a few presumptive tests that would help you to identify it.

For a more reliable and almost as eco-friendly approach, consider trying the CIELO method, which uses ethyl acetate - less toxic than IPA, btw - and calcium hydroxide aka pickling lime. Yields almost pure mescaline citrate on addition of citric acid to the solvent pulls.
Acetic acid 5%. The canola oil after the 2 days was no longer translucent but a yellow color. The vinegar was also clear and colorless until it was reduced then started to get the orange hue. The solids were with the saturated sodium carbonate solution... this was discarded but was pulled twice with the canola oil. If it didn't pull after 4 days not worth it. 2 days then 2 more days new oil

The IPA was used as an attempt to clean up the acetate further and wasn't needed really. I kept the pulls from the ipa and the precipitate but lost what I suspect was the acetate in the hot water bath and it wasn't worth boiling to me.

The cacti I used were outer green flesh from various bridgesii, pachanoi and lophophora williamsii they should be active. I started off with 9g of material so these values are not as low as they seem. "weighed 472mg"

Next time I'll keep the different steps until completion.

Mescaline acetate is protonated even between pka of 4.44-9.56? OR maybe just a positive charge under 4.44 ph? I'll likely just have to repeat this and test myself if the precipitate is worth the cleanup. I can test the ipa pulls that I believe are impurities. Assuming that the mescaline acetate is soluble it could be there.

As for the precipitate; pectin might fit but not really gel like also sodium acetate which I also suspected but since I lost most of my final product I'll just need to reattempt.

CIELO is a great method but ethyl acetate is controlled here in Brasil and requires a license. The next best step up would be d-limo but I'll reattempt my canola oil extract.


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4. I didn't use any heat so I followed the patents which say 30hours soak with mixing the two layers. I mixed every couple hours for 2 days at 20C. If heated this could be reduced to 1 hour to pull.

I did 2 pulls of oil which I believe is enough but if you want do as much as you'd like.

5. After separating the non-polar layer from the alkaline aqueous layer. I added a acidic aqueous layer to salt and pull the free alkaloids that should be in the non-polar.

Once I extracted dmt with vegetable oil, and it worked quite fine, it's not a bad nonpolar solvent, except for propensity to emulsion and high viscosity.

I would expect that oil could extract also mescaline freebase, but 2 pulls are not enough and more are needed.
Anyway, how good your oil extracts mescaline should be tested and confirmed.

Filtering/drying of oil after separation from alkaline soup would be also very beneficial. Oil should be clear, not murky, before acid pull.

I would expect mescaline acetate to be soluble in IPA, but have no experience with it. I would use different acid.
The oil got very murky from the alkaline aqueous pulls. After the acid pulls didn't change much.

I'll reattempt this in the future but don't have much means to actually test efficacy of the oil. I didn't use any filtration and had to do multiple cleanups by better separation.
Took a bit long composing all this, apols if it's a bit hazy and disjointed...

We need to clear up how it is with mescaline acetate, conceptually. Perhaps it would be more helpful, onomastically, to refer to it as mescalinium acetate, so we have a similar distinction like ammonium salts vs. ammonia. That way we would distinguish between mescaline in its freebase form, and the protonated congener mescalinium. The pKa of mescaline is 9.56, meaning it is, in bulk, 50% protonated at a pH of 9.56. Where does the pKb 4.44 come from? The pKa of acetic acid is 4.76 which will nominally be 50% protonated at a pH of 4.76, except with weak acids and bases concentration effects come into play.

All in all, I think the figures aren't altogether that important considering the materials you've decided to work with. Just make sure you really grasp what each step of the extraction process is intended to achieve, where the actives are likely to be and what you can do to get them to where you want them to be.

I think leaving the oil and base mix for 2 days each time isn't helping. It can't be taking that long to break emulsions, I hope. Better to do more mixing for a shorter time and do more, smaller pulls. This will help minimise saponification. If the oil is coming out cloudy, letting it stand in a clean container will give time for water material to settle out. And if the oil seems too viscous for that - well, what options do you have for obtaining solvents. Things like naphtha or DCM might be helpful here but I guess it's a bit tricky to find stuff like that in Brazil.

Also, considering mescaline itself is colourless the development of a yellow coloration can only be due to impurities.

Alternative is to make mescalated salad dressing :lol:
Murky solvent most likely means some water has been mixed with the oil and impurities, dissolved in it came over into water pull.

Thank you for providing info about the patents, it's very interesting and helpful. Method used in EP2475374A2 is somewhat similar to first steps in Cielo - extracting from wet basic paste directly to nonpolar solvent.
Incidentally, I recently got some seaweed oil (algae oil) and was struck by how low-viscosity it seemed to be. My first thoughts included perhaps trying it as an extraction solvent, so this is that thought being put out there. We'll have to see if I manage to use it for anything like that - it's nice on the skin, easily absorbed. A bit pricey though.

Finding a nice, clean, low-viscosity oil is likely worth parting with a few extra pennies, I'd say.
I got the pkb from here. I don't know if it helps anything really just trying to explain the precipitate. Would a positively charged molecule be less soluble in isopropanol?

The understanding I have of extractions are
Base 2ph over pka so 99% free alkaloids
free alkaloids pulled with non-polar
acidify non-polar to salt out free alkaloids atleast 2ph under pka

Perhaps the cloudyness is wax esters from the cactus flesh/skin which makes sense.

The two days isn't to break emulsions as within maybe 30 minutes the two phases are already separated and might just be a means to better absorb/transfer of the alkaloids.
Wax esters, could be.

Mixing of the phases is when maximum transfer occurs - maximum surface area cross-contact. More pulls because mescaline freebase is fairly soluble in water. 2 days just sitting isn't doing much for that. Not nothing either, just not much.

A positively-charged molecule would still require a negative counter-ion, and this would determine the solubility on the basis of, well, a bunch of factors, like the interaction strength between the ions, lattice energies, ion-solvent interactions. Crudely put, if the total energy of solvation is less than that the lattice energy, the substance will tend to precipitate.
with the acidification, it's as much about converting all the alkaloid to salt form with the minimum necessary amount of acid. A few separate washes with a small amount of acid, while monitoring the pH, will achieve this more precisely than one wash with an excess. The reason for wanting to do it precisely is in order to avoid having to evaporate of excess acid, which is time-consuming, smelly and wasteful. But you can ensure that your acidic water starts 2 pH units under the pKa, at least.

Measuring the pH change in each pull shows you when to stop (the pH doesn't go above 7 at that point).
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