Would Gramine come through in an Ayahuasca (since it's nearly insoluble in water)?
Would acidic water pull it out?
What's the solubility of DMT in a plant in plain water?

While gramine freebase might be insoluble in water, like DMT, its protonated salt form (e.g., gramine hydrochloride/citrate/whatever) is going to be water soluble. The exact amount that can dissolve to saturation will then depend on the anion (in the case of the pure substance) or the other components of the brew, which, frankly, makes it seem unlikely that gramine will be present in high enough concentration to reach saturation. Then again, I haven't looked up the solubility of gramine salts so it's equally possible that something like gramine magnesium phosphate might prove to be highly insoluble above pH6 (just to provide a plausible but imaginary example).

At least half over my head as usual, good sir. So, DMT freebase is also insoluble and is what's found in the plant? And acidic water would make the same difference to both, I assume.

Gotta wonder if there is a way to get mostly the DMT and NMT while bypassing the Gramine in a simple brew. Also gotta wonder exactly how toxic Gramine is as well, there seems to be a question as to that. I know that Naptha extraction will leave it behind, but many seem to have been disappointed as to yield with that.

In the case of all alkaloids, gramine and DMT included, they will occur in the plant in the salt form. Purines like ceaffeine don't really count, for you pedants out there. Acidification is recommended as much because water supplies can often be slightly alkaline as it is to improve the alkaloids' solubility in the presence of tannins.

A recent thread suggests that gramine may not be all that toxic but I would still be wary of its headache-causing potential since having got one after munching a load of raw phalaris grass. In that case it could equally have been a coincidence, or due to stress, coffee or nitrates. There are still too many unknowns regarding the effects of gramine and 5-methoxygramine in humans and I think most people would be understandably reluctant to engage in experimentation. The possibility of adverse synergies cannot be discounted and, given the nature of the realms being explored here, fear and uncertainty alone can be uncomfortable travelling companions for the psychonaut, albeit not insurmountably so for a dedicated plant practitioner.

Great answer, as usual. Didn't know that about the salt forms, so thanks again for the teaching.

I am definitely experiencing the latter thing you mentioned quite a bit. I have a lot of experience with 5-Meo-DMT years ago as an RC. So, assuming fairly well made and pure.

I always got a "woozy" period right after the initial effect. The timeline was, an "alien" psychedelic effect which, after a while, turned into a woozy kind of feeling which reminded me somewhat of the feeling you get from inhaling solvents or sniffing glue (so, not good). That then gave way to a mild psychedelic afterglow.

DMT gives me the "alien" feeling initially, albeit less so. It's much more enjoyable, more importantly seems to have much more import. But, then I do get kind of a woozy feeling for a while (less so again, but definite).

So, now I tend to worry about there being solvent traces left. You nailed it. I'm probably worrying too much, but the uncertainty can be uncomfortable.

Interestingly, Acacia extractions do not give me the wooziness nearly as much. The NMT also makes things more "recreational" and less serious for when you want such things.

Hope you saw this, along with the post following it. The post preceding it was the interesting bit, but as Nen says, he deleted it. Dithyramb added a few links in an earlier post: https://www.dmt-nexus.me...mp;m=1227262#post1227262 so I hope you've been following that thread! They also provided a link to another thread about gramine.

Hey, thanks. I had been following one of those. That's what led me to start this thread.
I'm not too interested in Phalaris due to the 5-Meo DMT content.

Years ago, I obtained a "potent Phalaris clone" and started it in my garden. At the time, the Entheogen Review was touting using a wheatgrass juicer on Phalaris. I did so and got a product which was definitely mostly 5-Meo upon bioessay.
At the time, 5-Meo was becoming available on the RC market and thus this was not of great use to me.

I got one more, weaker, batch and then the Phalaris seemed to have become inactive. My theory was that it crossed or mixed with other grasses in the wild and would need to be grown separately, in a pot, to maintain potency.

It's a shame that one could not extract the DMT (and NMT) from Desmanthus with something like Limonene while leaving the Gramine behind. Extracting with a solvent like Naptha with a low yield seems like breathing the solvent would be as bad as the Gramine seems to be.
If you were going for Ayahuasca then you could even leave the DMT as a salt.

Anyway, sometime down the road I'll be seeing what I can do with my Desmanthus and am reading anything about it and/or Gramine with interest.

Preparative chromatography could be another good option for separating DMT from gramine - use a large enough sheet of paper and you might get a half-decent amount onto it.
https://www.dmt-nexus.me...spx?g=posts&t=103670

brokendownpalace10..I've put a revised assessment of Gramine in the thread DFZ pointed to
https://www.dmt-nexus.me...1229116&#post1229116
my assesment is safe in the amounts present in Phalaris, and it has anti-oxidamt and anti-mutanogenic activity, hence potential health benefits
yes you'd get it in a water boiled preparation...bothering to get rid of it sounds like a lot more trouble than its worth