Research 2020 Bufotenine Extraction TEK + Analytical Data

[Woolmer]

So I wrote in regards of Woolmer that the tan colour seems just like what I had observed for Bufo Benzoate. But then I again read your wiki article that shows super nice clear crystals of Bufo Benzoate. That would then make up the question why seems in our case Bufo Benzoate be more of a dirty tan opaque powder instead of your crystal clear beauty crystals? Actually expecting a pure product the nice pictures in your TEK look much more of a reasonable candidate for a pure product. And therefore I believe what you actually have received might be the true Bufo Benzoate instead of the dirty stuff that we have obtained.

The actual difference is:

I took some Bufo Freebase and converted it to Bufo Benzoate in the minimal amount of liquids to maintain minimal solubility. Woolmer took EA and then evaporated it further down. That means both our products were crystallized at pretty harsh conditions, while you crystallized your Bufo Benzoate straight from the extraction liquid. Therefore I am sure your conditions were much smoother, potentially resulting in a slower and therefore well-ordered crystallization.

BW please see the method I used in post #69 and the final results in post #71.

I never used EA or evaporated anything. It was acetone pulls without any prior defatting to which benzoic acid was added. After each addition of BA, the colour got whiter as is seen in post #71. I am sure a prior defat would have yielded a whiter product.

A thought I have re _Trip_'s larger crystals is that he left the acetone pulls for a few days (post #68 ) after which it would have picked up some water thereby increasing the solubility of bufo benzoate and leading to slower crystallization. Was your acetone dry before the extraction?

My acetone was dried beforehand and kept as dry as possible during extraction. After the pulls, it was dried again. The addition of BA immediately made small chunks of precipitate and after 20 minutes a sheet would cover the bottom of the dish.

I think adding water or not drying your acetone could lead to larger crystals, but may decrease yield. Should not be difficult to test I may give this a go.

Would love to hear more feedback on activeness of the crystals when you're up to explore it further Woolmer. I think lab testing would really bring this home and give us a good idea of what's exactly being yielded.

I will have more chance to assay in a few week's time. Unfortunately, I think it will be very long before lab test results come in. Our postal system is very poorly run and packages take months to reach their destination, if they ever do. I will try to get hold of some TLC plates in the meantime to do qualitative analysis.

 

[_Trip_]

There could be several reasons for the larger crystals. My seeds were well spent by the time I did the acetone experiment. I had experimented with the 50g of seeds I had in every way possible. Multiple defats with different solvents etc. Likely the lower yield on the spent seeds likely cause the slower crystallisation. I left it for weeks before I checked it.

Regardless woolmer love your work.

 

[Brennendes Wasser]

I never used EA or evaporated anything. It was acetone pulls without any prior defatting to which benzoic acid was added. After each addition of BA, the colour got whiter as is seen in post #71. I am sure a prior defat would have yielded a whiter product.

Ah then there was some mis-read. But then this is pretty forward, just extract with Acetone and dump the Benzoic Acid.

I think the water was not the reason, so better not add water further into the Acetone. Should be always fully dry.

And yes that defat would probably have changed something. Its quite easy to simply do the boiling Naphtha rex, as it luckily should take away all other (potential) alkaloids and fats. I guess that could have been a reason for the super nice crystals of _Trip_. But even when getting brown flakes with defat, it could still be pure regardless of shape/colour. As I said when going with minimal solvent amounts the bufo benzoate crashed out as some tan powder also.

So just as a sidenote to crystallization, even small impurities can greatly change the shape/colour of any crystals. Any crystallization act is a process of slow molecule aggregation, whose orientation is determined by a specific energy minimum that each molecule will have when incorporated in the crystal grid. That energy minimum is an inherent property of the molecular structure, so any change in functional groups or constitution might completely change the whole appeareance - as seen with the pictures I posted here across from DMT / Bufo / 5-MeO. Now if any impurities are present, they might steal their way into the growing crystal, effectively creating defect areas within the grid. At these positions the molecules cannot exhibit their thermodynamically-designed orientation and thus the growth of the crystal itself will get a defect. Therefore even small impurities might change the appeareance and mostly for the bad, meaning that sometimes crystals will not even form.

A lower concentration in general might prevent building-in of defect areas, as the impurities are also simply diluted and not so prone to snatch into the growing crystal. Therefore creating crystals from a really low volume will mostly give uglier crystals, also because the overall crystal growth speed is much higher (if precipitation is then much faster due to low volume). This itself can also create ugly crystals even without impurities.

If you all have Benzoic Acid you could make a cool experiment. Dissolve quite some in hot Toluene or Naphtha or Limonene and then let it cool back to room temperature. Even with super fast precipitation Benzoic Acid will give crazy needles, looking quite cool. Still I guess there is no tool to foresee crystal geometry based on molecular structure. But maybe in the case of benzoic acid this really well-ordered crystallization comes from the fact that it has 2 very different structural features (Benzene-Ring + R-COOH) which are truly forcing the molecule to only have 1 very specific orientation, making it hard to ever create defects. On the other hand Tryptamines have their flexible side-chain, which can have a multitude of orientations and therefore cause some anger when trying to crystallize it.





Furthermore a funny anecdote:

Speaking of harsher crystallization conditions when impurities are present, there is a funny story from biochemistry research. In protein analysis it is obviously one of the most important things to access the 3D shape of a protein, as this will make you able to understand its function. This is generally done by crystallizing the protein and then using X-Ray spectroscopy to create a 3D Map of the individual amino acids. I cant remember which protein this is about, but a pretty "important" protein never could be analyzed and the 3D shape was unknown, as the Protein was never pleased to crystallize in any lab conditions. Then finally the mystery got solved as crystallization worked and the 3D shape could be uncovered - but then there was the super funny realization that when building up the protein with Amino Acids, there was actually a "defect", unintentionally exchanging 1 Amino Acid with another one due to bad lab work. And this single exchanged Amino Acid (from 100+) suddenly enabled the Protein to crystallize

Quite a funny story how 1. bad lab work made a great next step in science and 2. actually incorporating an impurity was the only (yet not even planned) chance to even get a crystal.

 

[Brennendes Wasser]

Just a small idea here, when _Trip_ came up with the idea to directly salt out Bufotenin with Benzoic Acid and use it straight away I was arguing that the salt might still contain some contamination, which is removed by toluene. Luckily you still tried it and got those super nice bright crystals. Just based on the look I was thinking that looks definetly not defiled with any other stuff, which would go straight against having any more gunk inside.

Check what I meant on the picture on the right.

Furthermore I would even have no idea what this powder could be in terms of contamination. It is also coming from the salting step, so it has a N in its formula, most certainly being an Alkaloid just like Bufotenin. But it would be even more polar and not dissolving in boiling Xylene. That would be reaaaally weird and unusual. On top of that, what alkaloid would that be ??? I mean I dont know too many unusual ones, but the only more polar are stuff like Bufotenidin (= NMe3+ instead of NMe2) and this stuff would be only present in traces. Actually at 140 °C you also degrade Bufotenin already slowly, but then it will form a dark-brown layer burned into the glass and not fine powder. So this all made 0 sense so I was thinking about this again.

Now I think I came to a logical solution, but of course cannot prove just now. And if this would be right, then I was telling crap that there would be any contamination left behind in the final product.

Idea is:
In this TEK the freebasing of the Alkaloid(Bufotenin?)-Fumarates is done by adding them in water to another water + saturated Na2CO3. Then the freebase is instantly created, forming a goo, which will collect to a ball. This formation is pretty fast so it will be voluminous, incorporating lots of the liquid around it. This liquid is water and is boiled off when doing the Xylene-REX at 140 °C. So I believed nothing would stay behind. BUT the water is saturated with Na2CO3. Of course this does not evaporate. And while the Freebase is constantly travelling into the boiling Xylene, it will start revealing the incorporated Na2CO3 again. And the more the Na2CO3 is getting uncovered, it will form more and more a solid powder. Voila! Now why is this powder brown as seen in the picture? The Bufotenin that partially degrades already at 140 °C will burn into the Na2CO3 instead of into the glass. This will give it the brown shape, yet being free-flowing as seen in the picture.

So I have no proof for this, but in my mind it makes 100 % sense and therefore it that would be true, you could directly salt out Bufotenin and use it. People who just want to eat it could directly use stop at the end of step #4. And people who want to smoke it could simply salt it out with Benzoic Acid - without boiling Xylene stuff. Pretty much the TEK that you already wrote at the wiki! And Woolmer may have simiply gotten not that nice crystals, because of no Naphtha defat, that would have removed other trace Alkaloids, that now co-precipitated and disrupted formation of the nice bright needles and stars. So long story short, no proof for this but I believe my argument for not-skipping that toluene REX was pointless and your TEKs should might likely give same purity with way less steps.

 

[Loveall]

Thanks for all this work

I followed _Trip_'s published TEK (in his signature) with a few simplifications (no seed toast or washes). The process is similar to what Woolmer did and product looks similar.

- Ground 4g of seeds on a mortar and pestle
- Mixed in 1g of Na2CO3 and 3g of water which was plenty to wet it all. I'll use even less water next time.
- Dried in the oven at low heat (170F).
- Single acetone pull (~40ml, did not measure exactly)
- Dried over CaCl2, decanted/filtered acetone
- Added a dash of benzoic acid to acetone. Didn't cloud so I though I had failed...
- Put in the fridge since the TEK says to be patient...
- Seeing beautiful xtals this morning (see first image). What a nice surprise!
- Caught xtals in filtere and washed with acetone. Also ground them up for intranasal route. They are sparkly and slightly tan (second pictute).

I think I have enough to do a bioassay. Up the nose? Dosage? I know nothing about bufotenine, so following in Ott's intranasal suggestions (see attached) will start at 20mg for the benzoate salt (Ott used free base up to 100mg).

Notes: I guess the oven dry dry also toasted oils and proteins (?). Perhaps if the intial toast is ommited a heated dry is necessary (?). Or maybe no heat is overall OK and perhaps better if bufotenine is sensitive to heat(?). Skipped the boiling naphtha and xylene cleans hoping that benzoic acid is selective and the smaller ammount of benzoates can be washed later if needed. Finally, how does bufotenine dissolve in acetone? Sodium carbonate should add OH- to it and make it not soluble in acetone (???). Perhaps drying with heat makes bufotenine neutral????????????? Drying alkaline mescaline paste with heat makes it insoluble in solvents which has allways baffled me (wetting the paste makes mescaline soluble in solvents again). Perhaps drying can change some alkaloids???

Cheers

 

[_Trip_]

I wish I hadn't mixed up my samples and got them tested (which really made me doubt myself). Then we'd probably have a better idea. Have you got any reagents to confirm we definitely have bufo benzoate.

Defatting could be essential? I think if anyone can get some samples off we'll have an easier time dialing it in. But thanks for giving it time Loveall.

I never tried it via intranasal but I think Ott said it was active at 6mg via smoking. I found it quite active at low doses with the small amount I originally pulled.

 

[neurobloom]

Quiet brilliant work guys. I personally haven't worked with bufotenine before but my recent experiments trying to crystallise phalaris aquatica freebase oil lead me here.

I was actually able to get decently clean crystals from fresh leaves using a standard a/b extraction with no defatting step and salting with oxalic acid. It's unbelievable how easy and rapidly the oxalate salt form crashes out as crystals. No evaporation is even required. No heat or cooling.. the crystals crashes even while separating the salted aqueous layer. Some crystals also crushed inside the non polar solvent.

I tried to redissolve the tryptamines oxalate crystals in water but it was poorly soluble. It took considerable amount of water to only dissolve half of it..so I gave up trying to dissolve it completely and added base and pulled again to end up with clear light yellow oil again. However the bioassay proved the extract was so much cleaner in quality.

I wonder if the success using oxalic acid on phalaris extract could be transferred to crystallise bufotenine.. having low solibility with high tendency to form crystals plus being non hygroscopic. It seems to be like oxalic acid is a great candidate..

I also thought about drying the O.A and sublimate it to obtain it in gaseous form which I can bubble into a non polar solvent saturated with the desired Tryptamine or better yet dissolved the dried O.A in dry solvent of choice and add it to your solvated tryptamine like you would do using fumaric acid in acetone.

I don't know why the GIFs does not play unless I tap to save them on my phone so you might have to tap to save if you run through the same issue.

Second GIF is trying to dissolve the tryptamines (haven't analysed the extract yet) oxalate salt in water. While it didn't all dissolve the left crystals got even cleaner.

Third GIF is the basing step of the partially dissolved crystals. It clouded exactly like the GIFs I saw above on this thread. Upon addition of chloroform to the based solution the cloudiness decreased substantially but not completely.

 

[Brennendes Wasser]

Notes: I guess the oven dry dry also toasted oils and proteins (?). Perhaps if the intial toast is ommited a heated dry is necessary (?). Or maybe no heat is overall OK and perhaps better if bufotenine is sensitive to heat(?). Skipped the boiling naphtha and xylene cleans hoping that benzoic acid is selective and the smaller ammount of benzoates can be washed later if needed. Finally, how does bufotenine dissolve in acetone? Sodium carbonate should add OH- to it and make it not soluble in acetone.

So you say maybe a heat dry would be mandatory, but just from the appereance your crystals look pretty cool? So I would assume when extracting from a wild mix like in any plant matter and actually getting something which is as crystalline (and light coloured) as yours it looks already pretty great. So even based on your results, maybe all that additional dry etc. is not mandatory?

Maybe if you could do a TLC it might be interesting to see if it only shows 2 spots (Methanol + 1 % NH3 = Bufo roughly in the middle and Benzoic Acid running totally on top). Of course it could still contain some Terpenes and similar, but those should pretty surely be cut off when doing the salting. So if truly only Alkaloids were extracted, you could only have a DMT/5-Meo-"Contamination".

About the Sodium Carbonate and neutral Bufo:

So it indeed dissolves perfect in Aceton, but if you wonder because it should be actually Bufotenate/DMT-O(-):

Indeed from pKs it looks like Na2CO3 would also react with the phenolic R-OH, but it seems in reality it does not happen ... that is why Na2CO3 seems to be the base to go to freebase Bufotenin. Everything with Hydroxide definetly produces Bufotenate. But Carbonate seems ... still not strong enough?
You can easily still dissolve whatever comes out from reacting a Bufo Salt with Na2CO3 in suitable NPS. So I simply assume that either there is no reaction of CO3(2-) and Bufo-OH or it is negligible.

OR last option it reacts with partial Bufo molecules, rendering only some insoluble. But then the yield could be actually even higher, if some Bufo might get lost there.

Sadly there is no inorganic base exactly between NaHCO3 and Na2CO3 that came to my mind, but at least with Na2CO3 you can freebase, while also extracting the product into Aceton.

I know nothing about bufotenine, so following in Ott's intranasal suggestions (see attached) will start at 20mg for the benzoate salt (Ott used free base up to 100mg)

I dont remember what I tried, but Ott's values were definetly not really psychoactive, a true "trip" would need more from my experience ... But not sure if ingesting as salt vs. freebase makes any difference here. Worst case you could store it as the Bufo-Benzoate and then upon need just quickly transform with a tiny amount of Ca(OH)2. Would be still much more relaxed to ingest than full seed powder.

Put in the fridge since the TEK says to be patient...

I wonder what would happen if you put into Freezer - Aceton cannot freeze (also you already removed all the water), so would be good to know if even more precipitates. Would otherwise be a pity to loose some goodies unnecessarily. That might be interesting, because _Trip_'s TEK is sparing out the nasty Xylene boil and goes directly into the favorable product, so it would be the preferred way to go for Bufo in general.

I wonder if the success using oxalic acid on phalaris extract could be transferred to crystallise bufotenine.. having low solibility with high tendency to form crystals plus being non hygroscopic. It seems to be like oxalic acid is a great candidate..

Cool finding, I thought Phalaris was mostly too difficoult to get crystallization happening. Oxalic acid seems to be indeed a good candidate, but what sets it apart from Fumaric Acid is that too much of this would be maybe not favorable, due to the kidney-stone formation over time Principally could be indeed used to crystallize Bufo here, but then I would not know why not to directly use Fumaric Acid or (in this special case) even Benzoic Acid from Aceton.

Normally Benzoic Acid dissolves so well in Aceton on its own, that any Alkaloid-Benzoate will not precipitate, but Bufotenin seems already so Polar on its own, that then after salt formation Aceton cant even handle it anymore.

Second GIF is trying to dissolve the tryptamines (haven't analysed the extract yet) oxalate salt in water. While it didn't all dissolve the left crystals got even cleaner.

Oxalic Acid on its own already has only a mediocre solubility in water, so I would maybe not be too astonished to see the Tryptamines only moderately dissolve. Could be a reason to go back to Fumarate, but of course not if Oxalates are better at generally remove the Alkaloids from the Phalaris Mix.

Same interesting story with the Kidney Stones upon eating too much Oxalic Acid:

Kidney Stone = Calcium Oxalate

Oxalic Acid = low-solubility Acid
Calcium(2+) = low-solubility Kation

On the other hand this unusual property of Calcium helps a lot in CIELO TEK, as the low solubility of Ca(OH)2 is the reason that we get the grainy consistency of the Paste, that can easily be stirred and decanted, while any high-solubility Base (NaOH, Na2CO3) would produce a sticky goo. So even low solubility might be helpful in certain scenarios.

 

[Loveall]

Indeed from pKs it looks like Na2CO3 would also react with the phenolic R-OH, but it seems in reality it does not happen ... that is why Na2CO3 seems to be the base to go to freebase Bufotenin. Everything with Hydroxide definetly produces Bufotenate. But Carbonate seems ... still not strong enough?
You can easily still dissolve whatever comes out from reacting a Bufo Salt with Na2CO3 in suitable NPS. So I simply assume that either there is no reaction of CO3(2-) and Bufo-OH or it is negligible.

OR last option it reacts with partial Bufo molecules, rendering only some insoluble. But then the yield could be actually even higher, if some Bufo might get lost there.

Sadly there is no inorganic base exactly between NaHCO3 and Na2CO3 that came to my mind, but at least with Na2CO3 you can freebase, while also extracting the product into Aceton.

Edit: OK, I had a bad theory I deleted. Thanks BW/DFZ.

 

[downwardsfromzero]

Indeed from pKs it looks like Na2CO3 would also react with the phenolic R-OH, but it seems in reality it does not happen ... that is why Na2CO3 seems to be the base to go to freebase Bufotenin.

Indeed, we can see here that phenol itself is not sufficiently acidic to react with Na₂CO₃: Phenol Preparing, Reactions, Physical Properties
Phenol will be released from sodium phenolate by carbon dioxide/carbonic acid, since carbonic acid (pK₁=6.77) is a stronger acid than phenol (pKa=10.0).

I would strongly suspect that indol-5-ol is even less acidic than phenol itself, making the situation for bufo freebase even more favorable.

 

[Loveall]

Indeed from pKs it looks like Na2CO3 would also react with the phenolic R-OH, but it seems in reality it does not happen ... that is why Na2CO3 seems to be the base to go to freebase Bufotenin.

Indeed, we can see here that phenol itself is not sufficiently acidic to react with Na₂CO₃: Phenol Preparing, Reactions, Physical Properties

But, according to this, phenol does react with Sodium Carbonate (and not sodium bicarbonate):

With sodium carbonate or sodium hydrogencarbonate

Unlike the majority of acids, phenol doesn't give carbon dioxide when you mix it with sodium carbonate or sodium hydrogencarbonate solutions. It isn't acidic enough...So sodium carbonate reacts partially with phenol to produce a solution containing sodium phenoxide and sodium hydrogencarbonate, but doesn't go any further. And, of course, it won't react with sodium hydrogencarbonate itself.

For bufotenine pKa1=9.23, pka2= 9.91

Therefore, the ideal pH is 9.57 to extract bufotenine with acetone. Above pH 9.9 we should start to lose yield.

What confuses me is that with sodium carbonate (pH ~11), we should be getting sodium bufotenate and no yield.

BUT, I think we don't have sodium carbonate alone. Yopo seeds have a lot of alkaloids. A significant ammount of sodium carbonate reacts with the natural salt of bufotenine to create sodium bicarbonate and "freebase" bufotenine. Other plant stuff (proteins, etc) also may react, increasing the buffering effect.

We therefore have a buffer.

I think it is the buffer system that makes this process work! Also, drying may help as excess sodium carbonate drops out of solution lowering the buffer pH.

One can play with the buffer calculator taking into account that 100g of seeds at 8% bufotenie salt will consume 4.1g of sodium carbonate when "freebasing" and generate 3.3g of sodium bicarbonate.

Ideal sodium carbonate considering the bufotenine salt conversion seems to be 6g. But there is other plant stuff so the ideal will be higher.

Overall, using too much sodium carbonate alone may risk some bufotenine not being neutral. Or maybe the natural buffer with all the other plant stuff is good enough if only sodium carbonate is added, especially when drying as not as much sodium carbonate can stay in solution and the smaller amount of sodium bicarbonate becomes more important (?).

Perhaps it is worth testing an extraction with leass sodium carbonate (~10g to 15g range per 100g of seeds). This may be especially true if we want to use a wet paste and ethyl acetate.

 

[Brennendes Wasser]

Therefore, the ideal pH is 9.57 to extract bufotenine with acetone. Above pH 9.9 we should start to lose yield.

What confuses me is that with sodium carbonate (pH ~11), we should be getting sodium bufotenate and no yield.

BUT, I think we don't have sodium carbonate alone. Yopo seeds have a lot of alkaloids. A significant ammount of sodium carbonate reacts with the natural salt of bufotenine to create sodium bicarbonate and "freebase" bufotenine. Other plant stuff (proteins, etc) also may react, increasing the buffering effect.

Yes indeed it simply looks like it still works. Yields of 1-3 % are also quite in the expectation range. That one report in the internet which is commonly cited with 6 % seems a little odd, not sure if thats more of an oddity.

Overall, using too much sodium carbonate alone may risk some bufotenine not being neutral. Or maybe the natural buffer with all the other plant stuff is good enough if only sodium carbonate is added, especially when drying as not as much sodium carbonate can stay in solution and the smaller amount of sodium bicarbonate becomes more important (?).

Still quite sure that this is also true! So at least some Bufotenin could very likely get Bufotenate'd :twisted: Maybe NH3 / NH4OH could be an alternative, but if I remember correctly it was not enough to fully freebase a DMT solution once, so I lost something back there ...

Organic amine bases which magically would sit somewhere in the suitable pKb range are bad, as they will be not removable ...

Perhaps it is worth testing an extraction with leass sodium carbonate (~10g to 15g range per 100g of seeds). This may be especially true if we want to use a wet paste and ethyl acetate.

Good call on your thoughts about Ethyl Acetate. I was worried when seeing you can crash out Bufo Benzoate from Aceton, that this reaction might not be running at 100 %. Solubility of any other Tryptamine-Benzoate is really high in Aceton. So naturally I would expect even IF you get Bufo Benzoate crystals, still a good amount might be hiding in the Aceton. With EA it would not happen pretty surely.



In general it would be cool if DMT-" and 5-MeO-DMT-Benzoate would stay dissolved in Aceton and/or EA. Because then you would not even need to do a hot Naphtha boil at the beginning.
Normally people might think, why exclude these? But at least for Freebase, removing them would be important for crystallization, but anyways on top their content is probably anyways always reeeeaaally low. Only for Yopo isntead of Cebil might be bigger. So when even doing the job of getting those seeds, you would probably prefer going to pure Bufo anyways. Plus it has the benefit that you can much better control your dosage, if no 5-MeO is present.

So the ideal new TEK might look like this:

Grind seeds to powder
Mix with Na2CO3
Extract with (boiling) Aceton/EA
Add Benzoic Acid, put into Freezer
= done (also wash crystals of course, optional = REX in suitable NPS, first try Xylene, then EA, then IPA)

The amount of steps here would be exceptionally low compared to original TEK No defat needed, because fats will stay in Aceton upon adding the Benzoic. But if you say pull from a Paste similar to CIELO, it might not work too well, because Na2CO3 will be sticky and not like the Ca(OH)2 in CIELO. But then if you use Ca(OH)2 you might will probably overshoot with pH. Another consideration should be: In CIELO you found the water content being perfect for later crystallization. But with Benzoic Acid any water will be a big problem, so you would need to totally dry your Aceton/EA before salting.
Other than this the Philosophy behind CIELO truly should be adapted to as many TEKs as possible :d Direct precipitation of a salt from the pulls is much better than anything comparable. Just finding the suitable salt-NPS pair is the task ... I'm astonished that it works for Bufo Benzoate in Aceton actually, as _Trip_ found out.


Just a small disclaimer: At least I commonly write BUFO for Bufotenin, maybe that could create confusion, as 5-MeO is commonly called Bufo in spanish communitys, as you derive it from the Toad / Bufo.

 

[Loveall]

I think _Trip_ tried the wet yopo paste and it did not work. Perhaps pH was top high in his situation.

If the ammount of sodium carbonate is reduced and a good pH is achieved, a wet CIELO paste could work. Ott was able to xtalize freebase bufotenine from ethyl acetate, so hot pulls are reccomened.

Fully drying the paste may shift the pH down as sodium carbonate crashes out making sodium bicarbonate more important, and bothe ethyl acetate and acetone could work.

_Trip_ did you ever try EA pulls on a dry paste? Or was it wet?

 

[Loveall]

Thanks for all this work

I followed _Trip_'s published TEK (in his signature) with a few simplifications (no seed toast or washes). The process is similar to what Woolmer did and product looks similar.

- Ground 4g of seeds on a mortar and pestle
- Mixed in 1g of Na2CO3 and 3g of water which was plenty to wet it all. I'll use even less water next time.
- Dried in the oven at low heat (170F).
- Single acetone pull (~40ml, did not measure exactly)
- Dried over CaCl2, decanted/filtered acetone
- Added a dash of benzoic acid to acetone. Didn't cloud so I though I had failed...
- Put in the fridge since the TEK says to be patient...
- Seeing beautiful xtals this morning (see first image). What a nice surprise!
- Caught xtals in filtere and washed with acetone. Also ground them up for intranasal route. They are sparkly and slightly tan (second pictute).

I think I have enough to do a bioassay. Up the nose? Dosage? I know nothing about bufotenine, so following in Ott's intranasal suggestions (see attached) will start at 20mg for the benzoate salt (Ott used free base up to 100mg).

Notes: I guess the oven dry dry also toasted oils and proteins (?). Perhaps if the intial toast is ommited a heated dry is necessary (?). Or maybe no heat is overall OK and perhaps better if bufotenine is sensitive to heat(?). Skipped the boiling naphtha and xylene cleans hoping that benzoic acid is selective and the smaller ammount of benzoates can be washed later if needed. Finally, how does bufotenine dissolve in acetone? Sodium carbonate should add OH- to it and make it not soluble in acetone (???). Perhaps drying with heat makes bufotenine neutral????????????? Drying alkaline mescaline paste with heat makes it insoluble in solvents which has allways baffled me (wetting the paste makes mescaline soluble in solvents again). Perhaps drying can change some alkaloids???

Cheers

Scaled up this for 100g of seeds and will measure yield. Less water used.

- 100g of seeds ground
- Mixed in 25g of sodium carbonate and 50g of water
- Dried paste in oven at 170F
- Pulled with acetone 3x (~175ml each time) trough filter
- Drierld over CaCl2 overnight which also allowed sediment to settle to a clear solution
- Carefully decanted and salted with 10g of benzoic acid

Brown xtlas are slowly forming (see image). Will post yiled when done. Will try to wash the dry xtlas to be white, hope simple acetone works...

 

[Loveall]

Saled up this for 100g of seeds and will measure yield. Less water used.

- 100g of seeds ground
- Mixed in 25g of sodium carbonate and 50g of water
- Dried paste in oven at 170F
- Pulled with acetone 3x (~175ml each time) trough filter
- Dried over CaCl2 overnight which also allowed sediment to settle to a clear solution
- Carefully decanted and salted with 10g of benzoic acid

Brown xtlas are slowly forming (see image). Will post yiled when done. Will try to wash the dry xtlas to be white, hope simple acetone works...

Yield was 7.7g of tan xtlas (1st image) after 24h. Roughly 4.8% freebase (minus any contaminants). Unfortunately xtals smell faintly of yopo seeds (nutty smell). Want to do a wash on this.

Washing with fresh acetone next to try to remove tan color. The tan color does not wash away quickly (very different than the EA wash for green mescaline CIELO which is instant), so I swirled the tan xtlas a few times in boiling acetone. Finally, after about an hour color cleared up significantly. Will update again with the yield and appearance/smell post hot acetone wash. Washed product is currently resting in the fridge with the fresh acetone cooling down.

 

[Brennendes Wasser]

- 100g of seeds ground
- Mixed in 25g of sodium carbonate and 50g of water
- Dried paste in oven at 170F
- Pulled with acetone 3x (~175ml each time) trough filter
- Drierld over CaCl2 overnight which also allowed sediment to settle to a clear solution
- Carefully decanted and salted with 10g of benzoic acid

Cool thing, quite low amount of steps! Also was the Aceton at Room Temperature? I think there is no reason why you cant also go to boiling @ 56 °C.

Also cool picture with the crystals ... I think just even getting ANY crystals is a high chance of having the desired product. Upon salting there is no other Alkaloid which should precipitate as "-Benzoate other than Bufotenin.

Yield was 7.7g of tan xtlas (1st image) after 24h. Roughly 4.8% freebase (minus any contaminants). Unfortunately xtals smell faintly of yopo seeds (nutty smell). Want to do a wash on this.

Holy crap thats a lot! When I did that old 2020 TEK it was always just 1-3 %.

So as you said, maybe there is the risk of partial Bufotenin-Bufotenate equilibrium, thus loosing some goodies at the end. But even on top the old TEK uses soooo many steps, that this is just alone a big reason for yield reduction.

The tan color does not wash away quickly (very different than the EA wash for green mescaline CIELO which is instant)

I would not be too distracted by an off-colouration. Bufotenin on its own has an increased electron count, so naturally absorbs more extended towards the visible spectrum. Same with Harmalas, which then have a tan colour. Even my most-rex'ed Bufotenin always had a slight tan colour. So naturally for the "-Benzoate it might be the same. So getting it not totally white might not mean anything, but of course washing it would be anyways desired.

so I swirled the tan xtlas a few times in boiling acetone

Actually I found it astonishing that Bufo-Benzoate even precipitates from Aceton. I would expect there is still SOOOOOOOME solubility here. So when going with boiling Aceton on the Benzoate, maybe just be very cautious by putting that boiling Aceton later on in the freezer and check if you get any Bufo-Benzoate back. Could be also reducing your juicy 4,8 %, even though a little bit of that may be contamination, but surely not too much.

Some things that would be now very interesting:

1. Solubility of Bufo-Benzoate in Aceton. You could measure 100 mg of your multiple grams AFTER cleaning and then boil in increasing amounts of Aceton until dissolved. Then after noting that volume also check how much precipitates in the Freezer.

Then it would be interesting if solubility in Aceton might be still "too high" and you could get even more after the salting step. Then Ethyl Acetate might be the candidate.

2. Before pulling, separating your seed/base powder into 50% 50% and do the comparable extraction with Aceton and EA on the respective parts. Then compare the outcome. I could imagine EA works better here, sadly its just a little less accessible.

Reason might be: EA might dissolve Bufo a little less well, but you can boil it even 20+ °C more. Given the assumption heat does not make any problems here, this will increase solubility even higher than Aceton at 56 °C. Then later when salting and putting to the Freezer, EA will definetly have an even lower solubility for Bufo-Benzoate.

So in total EA could make for a higher yield. But your 4,8 % is already super high, so Aceton might be still efficient enough.

Now last question of course is simply if that is indeed (nearly) pure Bufo Benzoate. Considering that there was no other workup step, it means the precipitation comes directly from a wild mixture of plant-derived molecules. Considering that you got ANY crystallization is a strong sign that we truly have Bufo-Benzoate.

But reason why it anyways would be very interesting to know, is that if that truly is Bufo-Benzoate from a high purity, then the old 2020 TEK here is quite obsolete, except if you truly want the Freebase (and I would not know any reason why this would be the case).

So if that stuff you got is already pretty pure, then this is a much better 2023 Bufotenin Extraction

EDIT: So just to make a very easy purity determination, do you have TLC Equipment and could make a photo?

It should look like:

TOP Eluent
Benzoic Acid
|
|
|
|
Bufotenin
|
|
|
START

In Methanol + 1 % NH3

No spot should be inbetween and definetly no spot remaining at the START.

 

[Loveall]

Thanks, BW.

Acetone removed some color but not everyting. Perhaps this is near the best I can get with acetone washes like you said.

Weight dropped to 7.5g after washing.

It is not soluble in PG or VG unfortunately.

Vaporized 10mg on e-mesh. It vaporized at low temp 100C (lowest setting but not sure how accurate the device is). It leaves a tiny bit of black residue behind. Felt the body relax a lot, no visuals though. No uncomfortable feelings at all. Matched what _Trip_ mentioned.

Going to explore higher doses. Also want to convert to freebase and make a vape pen for sure

Edit: Vaped 20mg while the after effects of 10mg where present and got nice visuals that where vibrating. No heaspace shift, just beautiful visuals as the body relaxes. I love it lol.

 

[_Trip_]

_Trip_ did you ever try EA pulls on a dry paste? Or was it wet?

Dry, don't recall doing wet. Unless I posted otherwise, I only remember working with dry paste.


Yeah I felt like the visuals were like psychedelic digital rain, but i never went too high a dose. Definitely a different body load than nndmt. More tingly all over felt good instead of the lead blanket feel with nndmt.

Good to know the tek is working for people. Yield seems high but literature does put it at 7.4% bufo.

Do you think an initial defatting could help loveall? Might not make much difference.

Also I think I had issues with EA and crashing out bufo benzoate.

 

[Brennendes Wasser]

Acetone removed some color but not everyting. Perhaps this is near the best I can get with acetone washes like you said.

Weight dropped to 7.5g after washing.

That colouration is exactly how pure Freebase Bufo looks, so would not worry more about colour.

And also no big weight drop, probably just fine now!

It leaves a tiny bit of black residue behind.

Probably this decomposition cant be avoided completely. Also the TGA vaporization profile of the "-Benzoate does not drop near 0 % like other "well-evaporating" Alkaloids, but also stops at ~ 30 %.

Going to explore higher doses. Also want to convert to freebase and make a vape pen for sure Big grin

Regarding the process:
I think now here there is no other true option than doing the Xylene-"Trick". No solvent can reliably crystallize it and even the Naphtha-EA mixture is bad, because solubility only drops to 1/3 or 1/4 at -20 °C. But with Xylene it drops to like 1/100. Limonene should be equally usable in theory, but it look always that I just destroyed the Bufo ... if trying must definetly stop at ~ 150 °C, more is unnecessary and quickly turns it black, same reaction like when smoking.

And testing a Freebase-E-Juice might be a great idea. So while I thought Freebase Bufotenin always decomposes strongly upon heating, it might not be the case for an E-Juice. When running the vaporization without Oxygen, it perfectly vaporizes. So reaction is definetly Oxidation-driven. But I dont think that this is just a mono-molecular process like Bufotenin -> Bufotenin-N-Oxide, but rather something that is only enabled by involving the R-OH. Otherwise also DMT would show this bad evaporation.

So very likely the decomposition is a oxygen-driven Oligomerization (sadly could not get any more details when I tried to provoke it and analyzing the residue), not proven, but probably most likely. And this of course occurs the fastest in a high concentration and evaporation of a pure Freebase oil = MAX concentration you could get anyways :twisted: :twisted:

So long story short: I think it's very likely that making an E-Juice from Freebase Bufotenin will maybe not show any decomposition or maybe at least greatly reduced. I said with the Benzoate there might not be a reason to ever go to the Freebase, but maybe the Freebase in E-Juice would show even LESS decomposition than pure Bufo Benzoate.

As I understand an E-Juice cant give you a rocket shoot, as the dose builds up slowly. But with pure Bufo a very big hit - at least for me - was anyways not possible with the pure Freebase. So maybe that might be an interesting alternative??

Simply if the long-term stability is not ideal, then what could still be tried is Bufo-Freebase in PG + Benzoic Acid in PG (with little excess of Bufo to be safe not vaping acid). Maybe formation in PG causes no precipitation and then it might be a Bufo-style E-Juice with longer shelf life ...


Great results definetly. But is there no vasoconstriction or similar effects? I often felt cold feeling in hands / forehead and unpleasant tingling ... :thumb_dow

Dry, don't recall doing wet. Unless I posted otherwise, I only remember working with dry paste.

Yes with Benzoic Acid the Aceton must be super dry at the end, the Benzoate should be super soluble in water, so any residual water should make problems when adding Benzoic.

 

[Loveall]

Thanks BW, no vasoconstriction noted.

A friend has also tried the bufo. He had rapidly vibrating visuals that responded to the music. He had some minor nausea and the very beginning of the trip, but not after.

I already did a conversion attempt to FB.

Calculated the sodium carbonate needed to covert to pH 9.6 (buffered with bicarb from first pKa) to be 3.5g. Added that at the same time as a small amount of water. Insoluble brown granules formed (see image). A sample granule was put in a tiny ammount of vinegar where it dissolved. Next time, I will dissolve the salt in water first before basing. EA and heat was added and the granules dissolved and moved to the EA giving it a tan color. Kept on pulling until all the water was absorbed into the EA leaving behind solids (sodium benzoate and sodium (bi)carbonate I presume).

The EA evaporated to leave a brown oil, but upon further evaporation the oil is changing into white solid film that I hope to scrape up (see second image). I hope this white stuff is bufotenine freebase and that it will dissolve in PG/VG. Vaping will be gentle for the bufotenine as it is aerosolized.