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The Bufotenin Problem - and potential ways around it

Migrated topic.
So now I tried to get a peak inside of how this Polymer might indeed look like. As I told some times, Bufotenin is getting brown to dark after some minutes above 140 °C and within seconds above 170 °C. Therefore recrystallization will always destroy some of your Bufotenin, if you have some black stuff left then this is not necessarily a contamination, but more likely destroyed Bufo. This black stuff will not dissolve in anything anymore unless it is DMSO and also give off no fumes. Therefore I believe it must be some kind of polymerization reaction which is discussed in the first post.

Here you can see pure yellow Bufotenin (will never be white) and the remaining black stuff.

Bu_re-x.png

Now I tried to provoke exactly this reaction to a maximum degree and see what changes I get in 1H-NMR. For this experiment neither a base-catalyzed (Et3N) or radical-induced (AIBN) way was chosen like for DMT, because here I just want to strictly get information about the decomposition products that you will get (and partially inhale) when smoking Bufo.

Now the predicted spectra is not included, but it is the same as in the post above for plain Bufotenin. Just like with DMT we would observe some polymerization happening if the count of signals at 6,5 - 7,5 ppm would be reduced - as exactly these protons would need to chip off in order to create new C-C-bonds required for Dimers / Oligomers / Polymers of the Indol backbone. Another sign of polymerization (via chinon-like structures) is the formation of the keton group. Then the phenolic proton at ~ 10,5 ppm would disappear or get lower in count.

20 mg Bufotenin for 10 min at 170 °C without any solvent until it's black.

Here is how it looks, sped up from 1 min to 35 seconds:

Bufotenin-200-C.gif

As this was still believed to contain some non-reacted, unimolecular Bufotenin, the glas was filled with Aceton and placed in a shaker overnight to remove every last bit of regular Bufo.

~ 5 mg remained (25 %) as a black residue

Now here is the 1H-NMR of that residue. Scan-Count was doubled due to low yield. Note that the labelling by that Software is again completely different than in the post before, but don't know how to set it by hand ...

B_Poly_-_beschriftet.png

Aromat count (6,58 - 7,14 ppm):
Bad news, all the Aromats are in perfect non-reacted conditions. Integral is basically exact the regular Bufotenin pattern. Based on this absolute no C-C coupling would have happened or if any, then at the lower 1-digit range.

Chinon formation (10,46 ppm):
The signal of the 5-OH is still pretty strong at 10,46 ppm. Actually it is not 1 like it should be in theory, but reduced to 0,85. But contrary to what people might believe this reduction from 1,00 -> 0,85 is not meaning 15 % chinon was formed ... Sadly Protons of these type (NH, OH, COOH, ...) are 'loosely bound' and therefore can get exchanged with Deuterium from the solvent. This always happens to a certain equilibrium which is dependend on the solvent used. Now the sad news is: In DMSO based on all my previous measurements the equilibrium is 0,8 - 0,90 :roll: So in other words: We have basically NO chinon formation. It could be checked by C-NMR, but I would need much more material for that, otherwise with 5 mg it will not give a reasonable spectrum. And for ~ 40 mg I would need to roast more than 100 mg of Bufo and I'm already frightened I dont even have enough left to try more Protocols to create 5-AcO-DMT :(((

N-Oxide (3,17 ppm):
If we just take a look at the N-Oxide formation we can see some, but only Trace amounts. 0,26 : 5,74 -> 4,5 % only. And this is only what we have in the sample, which was removed from the whole heated material. That means if we have 4,5 % in 25 % residual material, N-Oxide formation at 200 °C over 10 min was only around 1 %.

Impurities:
There is only 1 new peak at 2.11 ppm and it's rather strong. But must be some kind of Alkyl and no idea how that could evolve from a thermo-driven reaction.

Conclusion:
Sad story is there is no conclusion. The observations in real world by eye show a definite destruction of Bufotenin. Colour gets black, it does not vaporize at all anymore and will not dissolve - except in DMSO, but DMSO is the last resort anyways so that means nothing. Judged by eye this is some completely destroyed compound which should have 0 in common with the monomeric Bufotenin. Still NMR shows EXACTLY Bufotenin, with just some trace impurities, but those are in the aliphatic range and therefore sadly not too interesting or a good starting point for further assumptions. No clue which experiment I could do from now on, especially to analyze simply this black tar that you get when attempting to smoke the Freebase. I could try also adding Et3N or AIBN, but then this does not reflect the every-day-situation of smoking Bufo ... Whatever reaction is taking place, the Combination with Benzoic Acid at least can stop it. But would have loved to know what's going on ...



This analysis made me realize that I also made a mistake with the DMT experiments :? :? N-Oxide is not at 2,5 ppm, but ~ 3,2 ppm. That means 2,5 ppm was just the solvent itself and that changes the ratio of N-Oxide, thus also will change the amount of aromatic signals (as I always used N-Oxide + Freebase = 6). Therefore we will also have different signals for DMT and they will actually increase in size, which will make them probably just having the same issue like Bufotenin here: NO REACTION :x :cry: :cry: Seems like the hopes to get closer to a polymerized tryptamine structure were not filfilled with any of these experiments.

Will be corrected in other thread soon ...
 
Has anyone ever tried or verified this?

Did we just completly missed out on this one or just nonsense chemically?

(Maybe it's just another fanatasy story from our lost friend: 69Ron > Ron > Baron?)

Vaporized Extract : Anadenanthera colubrina (extract) - Erowid Exp - 'Vaporized Extract'

Creating the basic salt: "calcium bufotenate" with calcium hydroxide (Is this not what yopo sniff is made from?)

I have no PhD in chemistry but it seams plausible maybe?

Some quotes:

While in Brazil, I started to do many experimental extractions.
I tried many A/B extractions based on DMT, using naphtha, as the non-polar solvent, and it failed completely. I tried it with xylene, then heptane, and still no results! It turns out that bufotenine, the active chemical in the beans, is too polar for a typical A/B extraction to be of much use. Eventually I tried a more polar A/B extraction based on Jonathan Ott’s A/B extraction technique. It was the first one of several I tried that actually worked.

Not being at all satisfied with Jonathan Ott’s technique I played around with the free base bufotenine extract to find out which solvents it was soluble in, in hopes of finding a better extraction technique. I found free base bufotenine was soluble in water, acetone, isopropyl alcohol, dichloromethane, methyl ethyl ketone, and not soluble in xylene, naphtha and heptane. At pH 8-9 it was less soluble in water and more soluble in dichloromethane, however at a higher or lower pH, it was much more soluble in water! This made a typical A/B extraction inefficient because even at pH 8.5, free base bufotenine was still somewhat soluble in water!

So I played around quite a bit and finally invented my own very extraction technique. Here’s how it’s done. Boil the powdered beans in water made pH 3 with hydrochloric acid for about an hour, and then filter out the beans, and repeat 2 more times with new water, also made pH 3 with hydrochloric acid. Concentrate the combined water extracts down and evaporate to leave some solid brownish gunk. Weigh this gunk and measure out an equal portion of calcium hydroxide (the same pickling lime used to make Yopo and Vilca snuff!).

Evaporate the combined acetone to get an extremely potent extract that is nearly 90% pure calcium bufotenine, which is one of the most potent forms of bufotenine. It’s the form found in properly make Yopo and Vilca snuff that has been used for thousands of years in South America. It’s more psychoactive than free-base bufotenine and much more psychoactive than the acidic salt form found in the unprocessed beans.


I’ve read other reports of people getting nausea and vomiting from Anadenanthera colubrina beans. This is most likely do to the acid salt forms of bufotenine. The bufotenine in the beans needs to either be converted to free base bufotenine or calcium bufotenate or the effects are not as enjoyable. I experimented with different forms of bufotenine. I found the most unpleasant forms were acid salt forms and the most pleasant form was the calcium based basic salt form of it. For example, bufotenine hydrochloride can be made my dissolving calcium bufotenate (a basic salt form) in dilute hydrochloric acid.

In one test I took 10 mg of calcium bufotenate, a very strong visual dose for this form, and I converted it to bufotenine hydrochloride inside a test tube. After the liquid evaporated, I vaporized it. The effects are dramatically different. 10 mg of this acidic salt form produces very slight visual shimmering, no actual shapes or patterns are seen, I feel pressure in the head and body, and unpleasant nausea is felt for 2 hours straight! However, there is more euphoria felt. The pressure and nausea ruin the experience.

I also played around with free base bufotenine. This is more psychoactive than the acidic salt versions, and almost like calcium bufotenate, but not quite as visual, and produces a little nausea sometimes. I found that calcium bufotenate produces the strongest visuals and the least nausea of them all, if any. However, not as much euphoria is felt.

When calcium bufotenate is vaporized, even at high doses, at most I might feel a little uneasy in the stomach for about 1 minute. That’s it. The remaining 2 hours are purely enjoyable. I’ve never felt actual nausea from vaporizing calcium bufotenate. I’ve also used it sublingually. Sublingually the effect is more like psilocybin or LSD, with a deeper psychedelic experience that is not as visual as when vaporized. Again, I’ve not felt any actual nausea from using it this way.


Bufotenine is rather stable, even samples of snuff several thousand years old still contain quite a bit of bufotenine in them. When I came back to the US, I had left some calcium bufotenate sitting on my desk in the open air back in the humid hot Brazilian summer climate for many months. When I returned to Brazil, the calcium bufotenate had become a sticky goo, but when I tested it I found no noticeable loss of potency.
 
Bufotenines activity as a potent visual psychedelic has been talked about to an almost exhaustive extent here, for over a decade. Multiple people including Ott have shown this. No news here, but this thread is great and full of great data.
 
Also IME, and I did a lot of experiments with Bufo…it never mattered what it was based with, how it was extracted etc…it was always highly visual vaped as any base and always produced the same side effects.

I don’t see any real reason to believe Amazonian snuffs made by the Piaroa or the Andean snuffs etc to be anything more than freebase bufotenine. Salt form is used orally traditionally as well. It seems unlikely natives were seeking out calcium bufotenate etc though I guess it’s always possible.

For myself, I was able to verify it’s full activity, mirroring what Ron was saying at the time and what it had already said.
 
I am talking about using calcium hydroxide to convert the free base into calcium basic salt form called calcium bufotenate. Which should be both more potent, most visual and most euphoric with the least side effects. It can be smoked or taken sublingually (don't swallow!).

Normally I only see using sodium carbonate to convert it to freebase. But just as I suspected 69Ron talked about it (which doesn't make it untrue or is it debunked already?)


wow oh wow bufotenine success!! (wow oh wow bufotenine success!! - Bufotenine and 5-MeO-DMT - Welcome to the DMT-Nexus)

SWIM uses either sodium carbonate or calcium hydroxide and a little water. He’s shied away from using calcium hydroxide because it reacts with bufotenine. There are three stages of reaction between bufotenine and calcium hydroxide which are time dependant, the first is that it gets freebased, the second is that it gets converted to a different more hallucinogenic nicer compound of unknown identity, and if reacted further, it seems to inactivate it (at least for vaporization purposes). Sodium carbonate can only freebase bufotenine and doesn’t react with it. I don’t know why, but that’s the case.

The problem with using calcium hydroxide is that if left to react for too long, it alters the bufotenine making it inactive by vaporization, thereby ruining your extract. If only reacted for a few minutes, it just freebases it, and all is well. However, the intermediate reaction between freebasing and ruining your bufotenine, is an extremely nice compound, much better than bufotenine, DMT, etc. It is the best psychedelic SWIM knows of, but unfortunately to make it requires that the reaction time be just right. Too little time and the bufotenine is just freebased, too much time and your bufotenine can no longer be vaporized. I don’t know the optimal time to use. SWIM tried many tests and could not find a time frame that always worked. What he knows is that 24 hours is too long and converts the bufotenine into a non-vaporizable compound. 15 minutes is not enough and just freebases it. The time needed is somewhere between 2-6 hours, and seems to vary every time. The safest reaction time is 2 hours. That seems not to be enough time to get to the third reaction stage. And if it doesn’t work, and just freebases the bufotenine, and then you can do another 2 hours and it will usually work.

I HIGHLY RECOMMEND PLAYING AROUND WITH THIS REACTION. When the calcium hydroxide reaction hits stage 2, the results are nothing short of amazing. But when it hits stage 3 your fucked. So don’t do the reaction with all of your bufotenine. That’s why SWIM doesn’t use calcium hydroxide for extractions, and uses sodium carbonate instead. With sodium carbonate there’s no worry about ruining your entire extract, but with calcium hydroxide there is. I think probably sodium hydroxide would have similar reactions with bufotenine so it also shouldn’t be used for extraction.

The product of the stage 2 reaction with calcium hydroxide is smokeable,
about 1/2 the potency of bufotenine, has the same duration of effects (2-3 hours), the same onset of effects (2-5 minutes), and same peak (10-15 minutes). It’s visuals are of a completely different character. It’s more DMT-like, but much nicer than DMT. It’s extremely euphoric, up there with mescaline in that respect, and completely without side effects. It has a much milder feel on the body compared with bufotenine. It feels like an entirely different compound. It’s actually SWIM’s favorite psychedelic (bufotenine is his next), but since it has no name and it’s structure is unknown, SWIM doesn’t refer to it normally when talking about psychedelics. It is without the “mind fuck” of DMT, but visually almost identical.

When Yopo is made properly, the effect you get is from this stage 2 compound. It’s very DMT-like, and you might easily mistake it for DMT, except that the duration is 2-3 hours even when smoked and it lacks the “mind fuck” of DMT. Also you feel “grounded” with this compound whereas with DMT you can feel disoriented. It’s like a friendlier version of DMT. I think most people would prefer it over DMT. SWIM has given some to other friends and they all liked it more than DMT. However, that’s not the case with bufotenine. Some people like it, some don’t, and some people don’t get much visual effects from it. SWIM likes them both very much, but prefers the unknown stage 2 compound. It’s more visual and far more euphoric, and feels more body friendly.
 
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Sorry Jamie don't know if I understand? What is said already?

For myself, I was able to verify it’s full activity, mirroring what Ron was saying at the time -> So you did got and verify reproduce it to get this second stage compound? If true, then I seems that this should be superiour form and "the way" to go?

Reading about this form is actually the only reason that let me thought bufotenine maybe actually is worth a try.
 
I was never able to produce anything that was different from simple freebase before nine. AFAIK neither did jorkest. Phlux did a lot of work and concluded that it was the oxidized form causing side effects but I can not speak to that.

What I do not believe is that native amazonians or those in the Andes are making calcium bufotenate. I think Ott had this covered.

Freebase bufotenine is active enough to explain the traditional uses.

For this same reason I believe ppl could have used bufotenine containing toads providing other compounds don’t kill them.

I’m not disputing that maybe you can make something else, I’m disputing the idea that piaroa shamans were.

No one knows what Ron reall did, but it was clear to a number of us back then that bufo freebase was already a highly visual hallucinogenic tryptamine.
 
As far as I'm aware, "calcium bufotenate" is a hypothetical compound in that there has been no analytical proof of its existence. As a metallic salt it would also be involatile, making it implausible that this suggested compound would be behind the effects of vaporisation.

Personally, I've never prioritised yopo extraction since the side-effects always sounded too unappealing, but we still have to consider how the material which gave rise to 69ron's glowing reports was never subjected to any formal analysis. It's not entirely clear whether the nuances of subjective effects described for the products of each of the different stages of "calcium bufotenate" formation were consistent and repeatable. Perhaps it was autosuggestion, or variations in the source material or even subtle aspects of the extraction process itself giving rise to batches with a higher or lower content of DMT, 5MeO-DMT and bufotenine, and quite possibly also affecting the levels of unspecified unpleasant impurities.
I was never able to produce anything that was different from simple freebase before nine.
I've read and re-read this but still fail to grasp quite what you mean by "before nine". Could you clarify?

@Jahvisions - with 69ron and his glowing reports one always has to bear in mind that he was probably trying to sell something. In this case he probably had a ton of yopo to shift. Making unverifiable claims about the product of a hard-to-replicate process was typical of his approaach.
 
Hello, have you seen this thread?


Conclusion was that we were likely dissolving freebase in acetone (not a metal salt).

Because of buffer effects and drying, the thought was that after drying the alkaline paste, bufotenine was in freebase form therefore soluble in NPS.

Regardless of the experimental interpretation, several of us we were able to produce clean organic acid bufoenine salts with a relatively simple process. I believe none of us isolated a metallic salt experimentally.
 
Hello, have you seen this thread?


Conclusion was that we were likely dissolving freebase in acetone (not a metal salt).

Because of buffer effects and drying, the thought was that after drying the alkaline paste, bufotenine was in freebase form therefore soluble in NPS.

Regardless of the experimental interpretation, several of us we were able to produce clean organic acid bufoenine salts with a relatively simple process. I believe none of us isolated a metallic salt experimentally.

To add, a preliminary Tek was published by _Trip_

 
Transform…sorry the “before nine” was a typo…the sentence was to end at before. I can’t see the edit button but could also be my phone.

…And to clarify I am not disputing the existence of calcium bufotenate. I am not a chemist. My point is neither is a piaroa shaman. I strongly believe bufotenine both as an oral salt, as well as freebase snuff etc to be the active molecule such these people used.

Something new would be awesome, but I think it would still be new.
 
Transform…sorry the “before nine” was a typo…the sentence was to end at before. I can’t see the edit button but could also be my phone.

…And to clarify I am not disputing the existence of calcium bufotenate. I am not a chemist. My point is neither is a piaroa shaman. I strongly believe bufotenine both as an oral salt, as well as freebase snuff etc to be the active molecule such these people used.

Something new would be awesome, but I think it would still be new.
There's a time limit on edit availability. This is to help preserve continuity in the threads, so I'll delete the superfluous word for you.
 
Jah…it’s hard to say what was going on with the stages Ron talked about. This was like 15 years ago and still no one afaik has produced anything other than bufotenine. I think it’s reasonable to want to rule out the elimination of secondary compounds and oxides, like phlux was suggesting. Really everyone should go and find his posts on this, because he was convinced he could produce a cleaner extract by elimination of the oxide.

Personally I have broken through with freebase bufotenine into intense visionary worlds. Never did I extract something that lacked side effects, but at times those side effects could vary substantially.

Haven’t touched it in over a decade. It’s not as interesting as DMT.
 
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