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The Bufotenin Problem - and potential ways around it

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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.


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:


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 ...


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 %.

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.

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 ...
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