Does THH suppress the effects of DMT?

[Mindlusion]

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

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

 

[downwardsfromzero]

Revisiting this old (tangential) discussion, recently I did a crude comparison of rue tea made from boiled raw rue seeds and a brew made from ground, roasted seeds. The thing that was immediately obvious was the practically complete destruction of harmaline in the roasted seeds. This was very obvious when comparing the two brews side by side under a bog-standard 357nm disco blacklight. The roasted brew had only a pale bluish fluorescence compared with the intense yellowish-green of harmaline that could be seen with the raw seed brew.

It seems to be a reasonable hypothesis that at least with dark roasted rue seeds the harmaline is fully converted to harmine in under ten minutes. It's hard to say whether any THH was formed as well since only 3g of seeds was used, which doesn't exactly lend itself to an extraction and alkaloid separation on the kitchen level. It would still be sufficient for producing a sample for something more technical like GC/MS and is also very easy to replicate.

Pics attached below, although the camera doesn't do justice to how different the two brews appeared to the eye. The roasted seed brew is on the left, and the pic with three brews has a simple hot water wash of raw seeds in the middle.

 

[dithyramb]

I cannot say that I detected a feeling of higher THH in my roasted seeds experiences. If you ever do analysis please let us know.

 

[downwardsfromzero]

I cannot say that I detected a feeling of higher THH in my roasted seeds experiences. If you ever do analysis please let us know.

It makes more sense that the harmaline would simply get converted to harmine by roasting in the presence of air rather than magically disproportionating to THH as well, so it's not at all surprising to hear of your qualitative experiential assessment. The blue fluorescence from my roasted seeds does strongly suggest that practically all of the harmaline was converted by roasting until the seeds stopped popping.

From what I gather, harmine has a bluish fluorescence which is much weaker than that of harmaline. This was mentioned in the forum in some post or other. Can someone confirm this? My experience with the roasted seeds was also lacking in any of the effects that might be attributed to THH.

This roasted seeds question deserves its own thread, we're rather off topic now. Meanwhile, I'll take a look whether a more specific "roasted rue effect on alkaloids" thread exists already.

 

[Sabnock1990]

This could be why when i've roasted my seeds (in the oven), they seemed weaker in a way, but cleaner, and i still felt Harmine i'm pretty sure, but i didn't feel Harmaline from what i remember, it just felt different, which is one reason i went back to raw seed. It does make me wonder if Harmaline is either breaking down or converting into Harmine, i've actually still got a good bit of roasted seed iirc stored in a bag, so i may cook some up at some point soon and try an extraction on it perhaps.