So sadly currently I cannot find my original thread, where I was asking why the hell Bufotenin is stable for years, while Psilocin is accepted to be prone to fast oxidative decomposition.
Obviously if left non-extracted in mushrooms any enzymes can reversibly break down the Psilocybin/Psilocin again.
But even extracts of *pure* Psilocin were told to be non-rewarding, as also any (at least partially) refined material would quickly decompose.
An obvious answer would be that Bufotenin has a 5-Position -OH and for Psilocin it is at the 4-Position. But that is of course not the true reason behind that, so I was wondering in that thread what the hell that 4-Position would do. But I always thought the break-down is simply an equimolar reaction of 1 Tryptamin with 1x O2. And that really would not care too much about the OH- position.
Now since some years there has been research into the Psilocybin colouring reaction, where damaged tissue of mushrooms gets blue. Haven't read that articles except a summary, but I think the message was the tissue damage induces some oligomerizatiion of the Psilocin by oxydation. That compound is blue and therefore visible for us and may have a defending mechanism instead of the more obvious psychedelic effects of the Monomer that would scare off any intruder (except Psychonauts).
So here I just found a picture which is nicely demonstrating why the 4-Position is causing an oxidative reaction, which might not happen for Bufotenin. Therefore answering my question from 1-2 years ago. Probably you have seen something like this in that other papers, but here it's just easy to discuss the difference to Bufotenin - and that picture is cool:
Read the article
here. It must be said that this picture shows only a Dimerization, which normally does not occur - it goes straight to Oligomers. But still it shows the possible construction of higher molecular molecules from plain Psilocin.
What you see is a Quinon-like structure, meaning a 1-4-conjugation of both Indol-Bodies. That is also called Para-Substitution regarding the positions of the Oxygen and the coupled sister-molecule. Now if you compare with Bufotenin:
As you can see there is no 1-4 AKA para conjugation possible. That is why this pattern would be restricted for Bufotenin.
Still it has to be said that the authors also found an 1,2-substituted pattern. That would be an ortho-conjugation. This substitution mostly is also favored by effects that lead to para-conjugations. So in theory that could be also possible for Bufotenin as you see in the picture. Still, this 1,2-conjugation would be not favored for both Psilocin and Bufotenin if you consider steric hindering - also in aromatic reactions a 1,4-conjugation is therefore still preferred chemically.
So as a potential oxidative break-down of either pure Psilocin or pure Bufotenin by ambient oxygen is not mediated by Enzymes (which can sometimes easily overcome otherwise problematic steric hinderance) the disfavoring of a 1,2-conjugation might explain why STILL there is no oxidation for Bufotenin, even though it could form this 1,2-chinon-like Dimer.
So that all is just speculation, but in any case Bufotenin does not degrade at all and this could be a viable explanation.