I've been going over the gist of the limonene techniques for the past week, but the theoretical justification for the initial acidification step just does not make any sense to me, even though it apparently works. I started with the intial belief that the acid would be added later to possibly salt DMT out of a basic aqueous layer, but from what I can tell this is not the case either. Why do we take it as a given from this technique (what is the original source?) that any of the target tryptamines exist as tannates? I have found no suggestion of their being tannins per se, though MHRB may contain some of them, but why would the plant conjugate a relatively simple indole (or multiple conjugated molecules) with a hugely complex polyphenol like tannic acid, for which I haven't yet found the definitive isoeletric point or individual pKa's for any of the phenolic hydrogens--even for the free, in vitro species, though Wikipedia says that "its pKa" is around 6--or 10? (which? who knows). Drinking water pH is by no means exactly or even within +/- 0.1 units of pH 7 anyway--in my experience it is often still slightly basic already because of dissolved carbonates, bicarbonates and hydroxides. It seems in my head that all we are doing is giving the calcium hydroxide something to react with.

Furthermore, this does not even sound like a reasonable metabolic step for something trying to solubilize a small molecule like DMT or other small, foreign molecules for excretion--though I concede it may be possible that it is involved in biosynthesis in some species. Biosynthesis is on my plate for next year, so maybe I will be able to understand something I'm missing then. Would it not at this point be ether linkages (consider the fact that tannic acid is not a carboxylic acid), anyway? (Or would there be only weak H-bonding? Surely it does not form hydroxylamines?) In some cases ethers can be easily cleaved by acidic conditions, but I don't think adding 5% acetic acid (typical vinegar, among the other junk in there if extracted from a natural source) is going to make this happen at atmospheric conditions at an appreciate rate.

If it were indeed some mono- or poly-tryptamine complexed solid, I have read commercial descriptions stating that tannic acid is at least modestly soluble in plain water or alcohol (as one would expect it to be). Considering the huge difference in size and sheer number of phenolic hydrogens of tannic acid, it seems reasonable to assume that any DMT tannate complex would at least be modestly soluble in plain tap water as well--possily even lyzed by water? All of this seems even more confounding when one considers other tryptamines--even N-oxides!? I've scanned through the 20 pages of topics containing the word "tannate" and don't see anything very pertinent, so if I've missed something, please learn me and I will happily shut up. /ramble-off

Anyway, I'm trying what I would suppose is just a "straight to base" ( or: "god-I-hope-I-know-what-I'm-doing-so-I-don't-look-stupid" ) tek without the initial acidification after a bit of reading about DMT's chemical properties. I'm okay with this for now as I'd rather have answers to these questions than naphtha-soaked crystals sitting in my refrigerator at this point. I will spare details for now, but I had a 2:1 v/v mixture of very basic water:limonene with root bark sitting capped after vigorous agitations for about eight hours. After this period, there were three layers apparent from the outside.

After a single vacuum filtration of the whole shebang, there is already apparent crystal growth along the main interface (quite a thick layer, it seems; I'd be happy with anything above 0.25%) at room temperature, assumedly from evaporation of the limonene, but it looks like there is some emulsion or fatty material sitting near it that must've escaped the filter--although I'm not sure how: the aforementioned third layer. After I scrape the filters and hit the filtered solids again with limonene, I will run the combined fractions through the separatory a few times, evaporate the limonene layer and report back; if my yield is awful and further extractions don't bump it up, I will accept my foolishness and take this as a lesson.

Thanks, and sorry about the raving walls of text. I'm certain I'm just making this more difficult than it has to be, but my brain is fighting me to understand before I break down and get some 5% acetic acid and start over.

P.S. Anyone know a good substitute for silicon joint grease that works and would be compatible and relatively non-toxic if ingested?

good post
STB works very well with rootbark
A/B does not seem to offer and advantage in my experience

AllIDoisSWIM, are you talking about the acid soak before adding the base in BLAB tek (or the same with q21 etc?) ? In that case, I dont think the point is to really increase the solubility of DMT, because whatever salt form it is in mimosa, it is certainly already very water soluble. I think the point is more that the extra acid can further help breaking down bark and further releasing DMT to the acqueous layer, but IMO and IME this will make no difference with powdered bark, it might if its shredded bark (but then I would say its much more recommended to blend/powder the bark before using anyways)

As for the original question, no, its not accepted that it exists as tannates, but considering the tannic acid content, its an educated guess.. are there stronger acids naturally present in mimosa that we know of?

AlbertKLloyd, one great advantage of A/B is if you have a separatory funnel, otherwise all the mimosa solids will block the stopcock (unless of course you are using a solvent like DCM to pre-extract).

Along with that posted by endlessness, I like the fact that you can reduce the solution. I don’t personally like working with multiple litres of basic solution. Nowadays, even with larger extractions, everything can fit into a litre container.

Yeah.. I've done many different A/Bs and STBs and lately I rather work with A/B, I feel its much nicer and cleaner to work with two liquids than it is with a thick solution + solvent. There is easier separation of layers too.