A problem while performing Bufotenine extractions is an instability of Bufotenine in high pH media. It seems it gets destroyed in very alkaline conditions, while being rendered inactive. It is always just labeled as some Oxidation process and this may only occur to the phenolic OH. What I could think of would be the following reaction:



Here you can see: The phenolic proton is "acidic" with a pKs of ~ 10 and can be deprotonated by strong bases. This requires a more alkaline environment than the regular freebasing step of the amine - which is pH 9-10 for most alkaloids. Using very strong bases like NaOH is therefore not advised when handling Bufotenine, as it will most likely destroy the compound, hence every TEK recommends to only use soda (Na2CO3).

Now across the internet you can find some quotations of "Calcium-Bufotenate". This would be a salt formed when deprotonating the phenolic OH in conjunction with the counter ion Calcium. In theory one would easily achieve this by a reaction of 2x H-Bufotenine and 1x Ca(OH)2 (= Lime) and then evaporating the 2x H2O to give Bufotenine-Ca-Bufotenine aka. Calcium-Bufotenate:



Ca(OH)2 is exactly inbetween Na2CO3 and NaOH in terms of base strength. Therefore it should be strong enough to convert the phenol, but not as strong to cause immediate decomposition, like NaOH is reported to do. Here is some stuff that you can find about it while browsing the nexus or other sites:



On Erowid you will find a post reagrding how to produce it:

- Dissolve Bufotenine in a minimal amount of IPA
- Add the same amount of water
- Add some Ca(OH)2
- Let it sit for 2-6 h
- Evaporate everything
- Extract Ca-Bufotenate with Acetone, evaporate

On the other hand you can read the post by Entropy Mancer, which states that it should be impossible to form it: Ca(OH)2 does not dissolve in water and therefore both compounds will never be in the same phase in contact. This will practically render the reaction speed to 0, making any reaction impossible.

Now I tried to reproduce this myself:

50 mg Bufotenine + 39 mg of Ca(OH)2

In theory to fully transform 50 mg Bufotenine to Ca-Bufotenate, you will need 9 mg of Ca(OH)2 = 0,5 mole : 1 mole Bufo

Now by conducting the procedure mentioned above, one should get a leftover of 30 mg Ca(OH)2, IF Ca-Bufotenate is formed and IF it is soluble in Acetone.
If Ca-Bufotenate is formed, but not soluble in Acetone, then there should be a leftover of 89 mg after the Acetone pull in the end.
IF no Ca-Bufotenate is formed, then 50 mg of Bufotenine should be dissolved, leaving behind 39 mg of Ca(OH)2 after the Acetone pull in the end.

So I let it stirr for 5 h with just a minimal amount of IPA + Water. Afterwards evaporating everything only granted 69 mg in sum, even though the initial material was 50+39=89 mg. The lost 20 mg are exactly the amount of water, that is created upon combining 2x H+ with 2x OH-, evaporated as 2x H2O for every 1x Ca(OH)2.

I threw Acetone on it, stirred it for 10 minutes and evaporated the Acetone.


Weight:

Residue, not dissolved by Acetone = 60 mg
Residue, dissolved by Acetone = 8 mg

If no reaction happened, then ~ 50 mg of Bufotenine should be removed by Acetone, which it wasn't obviously.
IF Ca-Bufotenate formed and is indeed soluble in Acetone, then only 30 mg should be left over. No real answer to be given here ...

Now I placed both samples in water (what Acetone pulled over and what it left back) -> nothing dissolved
So either Ca-Bufotenate is not water soluble or no reaction happened (Bufotenine is only slightly soluble in water and Ca(OH)2 nearly not at all).


Evaporation:

My freebase Bufotenine that was used melts at ~ 104 °C (literature says 146 °C, still I can confirm I have pure Bufotenine) and starts evaporation at 180 °C. So by throwing both the Acetone-soluble and Acetone-insoluble samples on a hot plate and measuring the Temperature with a IR-Thermometer, I thought I may compare that new stuff's phase transition with pure Bufotenine.

But there is NO phase change. Even at 400 °C the stuff just remains brown powder. Not even a slightest hint to fumes. Then I torched it with a lighter from ~ 3 cm distance. The flame is at max 1200 °C and the samples just started to glow, not releasing any fumes nor melting.

IF Ca-Bufotenate is formed, it seems to have an insanely high melting point / vaporization temperature.
IF no Ca-Bufotenate formed, then of course the Ca(OH)2 has an insanely high melting point, indeed it decomposes instead as per Wikipedia. But still this remainder should consist of mostly Bufotenine and if the Ca(OH)2 inside of that sample is not melting, then the Bufotenine should definetly make any macroscopic change visible.



Left: both samples from that "Ca-Bufotenate conversion", left: Acetone soluble, right: Acetone non-soluble remainder
Middle: Torching the non-soluble remainder with a Butane flame. No visible degradation, just glowing
Right: Mixture of Bufotenine + Ca(OH)2 powder, starting to melt at 105 °C+

So in summary:

Sadly no clue what happened. I cant conform that a new compound was formed that is soluble in Acetone - only 8 mg of theoretically 59 mg was dissolved in Acetone.

But also in case there was no reaction and both Bufotenine and Ca(OH)2 are still present as monomolecular, separate compounds, then there should be a distinct temperature where you can observe the Bufotenine melting and evaporating.

To proove this I just mixed 10 mg Bufotenine and 10 mg Ca(OH)2 and mixed it to a homogeneous mixture. Now I placed it on a hot plate and the Bufotenine starts melting at 105 °C+ and it turns dark after 160 °C+ while releasing fumes.

So there must have been a conversion somehow, but whatever came out, it did not show the reported properties of a hypothetical Calcium-Bufotenate and it is not smokable.

I don't have much to add on the science but I'm interested in this as well. Last time working with yopo I mixed it all at once with calcium hydroxide and it ended up all destroyed, totally inactive. I did try a few hits of it at around the 2 hour mark and it was fantastic. I had smoked the seeds straight and there was body load and not many visuals even with multiple seeds torched. After about 2 hours with the lime just like ron said, a lot like DMT visuals but felt a lot less scary and more pleasant. I didn't smoke much only a few hits and was surprised at how much it hit me, when I wanted to smoke more I tried more from the same batch but found it was all now inactive and smoked the entire rest of the batch (50 seeds or so?) with no effects or barely any.

Once I mixed water, lime, and toasted ground yopo I got a very clear ammonia smell coming off my container. I still need to try with just washing soda and see if ammonia smell is there again but I think it's likely the lime causes some reaction.

I'm still trying to work out how to separate all the actives from the lime as soon as it's done before it gets destroyed. Maybe neutralize with vinegar, boil down, and then basify that with ammonia or sodium carbonate? I want to use all food safe if possible.

Wow, this is interesting.

But i have an old batch of yopo mixed with lime, and the last time i touched it, it was still active. Sublingually that is.

So the destruction of the molecule would happen when attempting to vaporise it then, i guess.

Yeah it just happened again actually. Just got some more seeds (vilca, colubrina kind rather than yopo peregrina this time) and they're way more potent. 1 or 2 seeds not even freebased can give me substantial visuals. I learned from last time and tried only 10 seeds toasted then mixed with lime and water. Tried smoking like 5 seeds worth and no effect not even body load. Smoked 1 seed raw/whole and instantly got the classic bufo body load and bufo vibes. Maybe I toasted too long or toasted when drying too much but I think it was probably the lime. I'm going to try washing soda tonight instead as ron who experimented a lot said that didn't react with bufo. ron was adamant about there being some chemical transformation happening while jamie disagreed. well i keep destroying it anyway so im just gonna use some washing soda now and maybe experiment with lime later.

im not going to try the inactive product sublingually because im not ready for that yet still dipping my toes in bufo space. maybe it is still active only sublingually. smoking is quite nice and easy to handle dont want it to get too intense.

Edit: got the seeds in with sodium carbonate right now. i just noticed this also appears to give off that ammonia smell mentioned by 69ron and others which i have noticed from pickling lime too. i mixed just sodium carbonate with water to make sure it wasn't just the smell of that and no it appears to be some reaction between the sodium carbonate and the seeds. sodium carbonate max PH is 11.6 and calcium hydroxide is 12.5 so maybe it's still high enough to do the destroying. i don't know if that's what the ammonia smell indicates

I seen this on another website which might explain the missing 20mg.


https://bluelight.org/xf...s-out-there.61866/page-4

Could it be the missing 20mg is the water created during the chemical reaction and was evaporated?

Aaaah great that is exactly the missing link! Ca(OH)2 is ~ 52 % Ca2+. So when doing the math, from 39 mg of Ca(OH)2 there should be 19 mg lost upon combination and evaporation ... so ... 20 mg lost is just about that

Great thanks for the hint and now corrected it upwards in that text.

Perplexing. The conclusion drawn from your experiment is that the bufotenine is somehow destroyed by the conversion method and also that it doesn't vaporize, yet it's contrary to multitude of reports of extractions being conducted this way from yopo seeds with active substance being yielded and vaporized. All this even though your experiment closely as possible replicates the original steps taken. I am perplex as you are.

The only difference I can think of is that the original extracting and basification also included the alot of the water soluble plant molecules and lipids, plus a whole bunch of hydrochloric acids.

Does the combination of 2x H+ with 2x OH- and loss of 20mg in evaporation mean that the calcium hydroxide and bufotenine conversion took place?

Also I'm wondering, if sodium carbonate was used instead of calcium hydroxide, as it regularly is in freebase extractions, would it not likewise form a sodium bufotenine salt, as [Sodium Carbonate Na2CO3 is the disodium salt of carbonic acid with alkalinizing property. When dissolved in water, sodium carbonate forms carbonic acid and sodium hydroxide]. So there is the same hydroxide and sodium in place of calcium.
I wonder what would happen if the same experiment was conducted using sodium carbonate.

This debate has been ongoing for over 10 years on the internet drug forums and the science is still not settled, as far as I can tell. I want to know what is being extracted using calcium hydroxide and what is being vaporized... what further experiments are needed to finally settle the science?

Also is this a typo in your orignial post. The word permitted. Should it read unpermitted?

No it is not destroyed within the conversion method, but it simply does not vaporize. If you heat it, it cannot vaporize, so you would use more and more heat and then ultimately it is destroyed, instead of giving off psychoactive vapor, that could be inhaled.

People who create a snuff that should at the end representate Ca Bufotenate could indeed be snorted and have psychoactive effects. I am just pretty sure that the "real" compound Ca Bufotenate cannot vaporize, which I think makes sense regarding its chemical nature. If people have smoked that snuff then getting vapor is still quite plausible, as it still contains all sorts of other things, that could be vaped. And it could be even psychoactive, as maybe a portion of Bufotenine is still in its freebase state and will vaporize. But when going 100 % pure it will not give any vapor and just be destroyed upon further heating.




I mean there was no advanced analysis done, but everything looked exactly like the conversion happened just as it should be. The weight change is now exact the water that should be lost. Also from solubility it acts exactly as I would assume (not soluble in water or acetone).




Here something different would happen: The base CO3 (2-) is not strong enough to react with Bufotenine in terms of Bufo-OH --> Bufo-O(-).
So the maximum reaction that could take place is conversion of Bufotenine(H+) --> Freebase Bufotenine, uncharged.

That is even desired in the TEKs here, as people have claimed (although no verification given) that Bufotenine would degrade at very high pH. At very high pH the only possible reaction pathway (although maybe triggering a cascade of other stuff, also discussed in this first post) would be the deprotonation. So for my TEK the goal was to NOT trigger this reaction, although no idea if that really leads to Bufotenine degradation over time.
In any way I have a true reason to not go with a strong base, because it will make Bufotenine insoluble in Aceton (as Bufotenine-O(-) instead of Bufotenine-OH) and my TEK was designed to extract with Aceton. So definetly Na2CO3 has to be used, to not over-deprotonate the Bufo salt. Also Freebase Bufotenine definetly evaporates, as seen here, but Bufo Benzoate works much better.




An easy proof to check if Calcium Bufotenate CAN be vaporized is to extract PURE Bufo, convert with PURE Ca(OH)2 and then deploy this sample to a Thermogravimetric Analysis. This will heat the sample and check if it gets less weight AKA evaporates. If it truly does not give off fumes (which is exactly what I saw) the weight should remain pretty constant at ~ 90-100 °C until 400 °C and then it would just disintegrate like any other molecule due to pyrolysis.

But I am now done with all my experimental stuff and probably will stop all activities so I tend to not buy or analyze anything anymore

Alternatively people could just place 30 mg of this compound on a 1 g microscope glass slide, place it on a hot plate at 250 °C for 5 min, breath strongly with air over it and then afterwards record the weight. If you still have > 20 + 1000 mg then you can be sure this is nothing that can be evaporated, hence be used as a psychedelic drug for smoking. If weight is at < 10 + 1000 mg I would say it could vaporize strong enough to get a true psychedelic effect.




Aaaaah yes I'm no native speaker and I thought permitted means forbidden corrected now.

Still I have to say I took that information (Bufotenine degrades at higher than pH 12) directly from Bluelight and 69ron. Still, I dont know if there has ever been a proof for this. I tried to get some insights into this here, but found no true conclusion.