downwardsfromzero wrote:The thinking here was that *perhaps* dehydroascorbic acid (= oxidising form) would serve to shuttle the hydrogen away from the harmaline, and the ascorbic acid (= reducing form) obviously transferring hydrogen to the harmaline to produce THH - thereby catalysing a disproportionation of harmaline to harmine and THH. I'm not saying it'll be quick though - nor even that it would work. Like I said, it was just one of those hunches. Most of my thoughts about this are already outlined above.
Maybe ayahuasca, as it seems, has other hydrogen transfer molecules such as flavonoids so the ascorbic acid idea is too over-simplified to work.
Practical experimentation has been inconclusive and as for the molecular orbital number-crunching required for a theoretical approach - that would take me rather a while from my present starting point
Mindlusion wrote:Don't you mean harmaline to THH conversion?
Depending on the circumstances, both are desirable. Getting the harmaline to disproportionate would be quite handy for making (harmaline-rich) rue brews a bit more caapi-like.
If dehydroascorbic acid (which is at least a dione) could act in a capacity similar to DDQ, well, I'd rather not have DDQ in my kitchen
This is entirely thought of as food-grade kitchen chemistry, much like ayahuasca brewing is (largely) food-grade.
Jagube - sorry, I can't answer your pH question because I don't know, although high pH should be taken to mean something more basic than neutral. But it's pretty clear that direct reduction of harmine to harmaline is difficult.
How this all relates to changes in alkaloid content during ayahuasca brewing, and the alkaloid content of
raw caapi, is a little foggy to say the least.
Ah, I read only harmaline to harmine conversion, missed the part about disproportionation.
So you're suggesting an ascorbic acid catalyzed redox process, I like this idea. Something like this must be happening in ayahuasca brews if THH is produced.
Obviously, the equilibrium leans to the side of the oxidized form of ascorbic acid, but its possible that oxygen from the air is the actual oxidant, and dehydroascorbic acid is the hydrogen sink and is regenerated.
And yeah you mentioned, metals such as copper, could certainly enhance this process. Oxygen as the starting oxidant, single electron transfer (maybe with a catalytic Cu (I)/Cu(II) cycle), to the harmaline, with the process ending with the electrons on dehydroascorbic acid.
But vitamin C alone I would think should be sufficient to reduce to THH in this case, hmm
Expect nothing, Receive everything.
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