The paper I linked proposes (and it has been shown before), that dimerization linkages actually occur from N1->C3.
This isn't particularly surprising, as autooxidation also affects that C3 position of indole.

https://www.ncbi.nlm.nih...re/F3/?report=objectonly

So would we need to worry about managing/minimizing this kind of linkage in the aqueous phase? Or do we expect the solvent to be able to break it up before precipitation? Thanks!

Most likely to happen as freebase in a concentrated non-polar solution.. especially in the presence of sunlight and oxygen, since it is likely in some part a SET process (autooxidation). Water might be involve as an addition product or source of H+. Benzyme, how is the resolution on the mass spec? enough to make out the gain or loss of 2H?, hard to say either way because in the spectrum we don't see a single mass peak but a range converging on a dominant peak. We should be able to tell in the mass spec if its a dimer + H2O or a dimer +H2


Really great paper by the way, Phil Baran is a legend. I worked on something like this too, Oxidative coupling of electron rich indole with aromatic amine (aniline, or indolent pyrrole NH) using hypervalent iodine.. this paper is a good example of showing that it's not so easy or productive with typical conditions. Thats also why I'm skeptical that the dimerization/polymerization products are anything more than trace elements, not really affecting yield, only to be concerned about in specific conditions

I should mention, while what was proposed earlier about dmt n-oxide forming a complex through non-covalent forces being incorrect, and this is testable, a mixture of dmt and dmt n oxide separate very easily in boiling hexanes. The DMT n oxide forms an oil that sticks to the glass.

Remember the use of the word polymerization should refer the reaction to form new covalently bound molecules, such as the dimerization being discussed above. The dimer being discussed now is likely produced through a radical initiator, atmospheric oxygen for example. Some amine oxides can also act as radical initators, some even form permanent stable radicals, and are used as catalysts for radical initated reactions (TEMPO). But these are formed from the oxidation of secondary amines, tertiary amine oxides have a very different electronic structure. Mind you, the presence of something like TEMPO could also have the reverse effect, acting as a radical quencher and inhibiting the reaction or interrupting it.

I just wanted to report, tired this tek with Acacia (Acuminata). As I'm sure many are aware Acacia (Acuminata) is notorious for pulling oily DMT. As are many Acacia varieties. I'm guessing this is one reason changa is so popular in Oz. I've found ways to get pure white crystals but yields drop dramatically. So this Tek looked very appealing.

When I first attempted this Tek I originally failed. Everything looked good but when scraping up the crystals I ended up with a oil that eventually turned to a wax.

However I have had some limited success with the shorter cooks (1hr) and use of KCL over CaCl₂. I also let everything cool without a fan and over a longer period of time.

Following the Tek strictly with Ascorbic/ KCL I was able to get .9% yield of very slightly waxy crystals. And managed to pull a further .8% of oily DMT using a (Toulene/ Heptane/ Hexane combination) after the naphtha pulls. (The oil pulls look like it might solidify).
These yields are decent considering its trunk bark not root bark and its not the narrow phyllode variety of Acuminata.

Also found that using a slow cooker that has a built in manual set temperature of 65c (149f) degrees to be invaluable. Set and forget.

The quality of naphtha (although is light naphtha) seems to have diminished over the last couple years in my country. So perhaps using a lighter fluid brand might perform better and crystalize better.

For anyone wondering I can't access heptane or hexane the use of a toulene/ heptane/ hexane was just a test, it was in a product I found that solely contained these three solvents mixed.


Edit: I have since refined my process with very good yields and end resulting with crystals.

Just reported in Max Ion thread, using Loveall’s improvements here, pull time down to approx 1 hour, with slightly better yield - Pure White, and significantly less work.

Great job, Loveall!

Btw _Trip_, a sous vide is the absolute best water bath tool (up to 100C) that i have yet found, better than lab equip…consistent, accurate control, in 1C or F increments, bluetooth-enabled, ramp down to ambient as slow as you want, almost hands free…then cook a gourmet meal…lol




Maybe some on this thread, could work on coming up with a very short, and equally or more effective, maceration tek that kitchen chemists can use. This would be a major practical step forward, for any extraction tek using woody material.

Yh never even heard of one might have to look into it.

It was the Taste ;D And not the smell. I guess it smelled like nothing - at least not the classic trypta tint Was like the ginger like spice, but with added sweet dash ...

Hi Loveall - Does this wiki tek refer to this process - the title is the same as another one of your teks so I assume you made a duplicate to get started and forgot to change headline since there's no mention of IPA or Acetone and much about DMT!

https://wiki.dmt-nexus.m...one_with_IPA_and_Naphtha

Yes, but based on Mindlusion's input, we only expect xtalization and polymers to form during the last part of the extraction, when the solid DMT forms. So that experimental TEK needs tk be reviewed with focus on that part.

I'm going to do some testing which I did not see in this thread.

I'm planning on performing 2 simple STB extractions with variable timing between pulls.

My procedure will be following Noman's tek, with some simple changes based on the min-polymer tek from this thread



If polymerization is happening during the base phase, we should expect lower yield on the vessel where we waited a day to do a pull.

If a test like this has already been performed, please let me know! I did not see it in the thread.

I don't believe this has been done. Perhaps is better to not add the naphtha or salt until the time of pulling? This would give a better chance to polymerize and see a difference. I think it could be could be lower yield or more DMT polymer goo depending on the pulling temperature (room temp and warm temp respectively). Thanks.

Noted. I'll make the suggested adjustments!

Jacubey - the one thing in your method you might want to change is that you add the salt before you add the lye, because salt dissolves more slowly and to a lesser degree than the lye does. That might provide a small time saving. Of course, this doesn't apply if you decide to hold off on the salt and naphtha as per Loveall's suggestion.

I think I'll go loveall's route. If the goal is to test the polymerization of DMT in the base, then the first order of business ought to be to confirm that it happens at all. I'll try to give the polymers the best chance they can have of forming.

I wonder if I should wait longer than 1 day.


Another thing I hadn't thought about last night is that dmt-oxide could still be a factor cutting in to yields. I think it would be best to do a room temp pull, immediately followed by a heated pull (say, 70C). The heated pull ought to have a higher yield in solution that's been marinating longer compared to the short, while the cold pull ought to have higher yield in the shorter sitting. This assumption could be wrong though, because the pH strength will largely determine how quickly freebase is released in to the solution. There is a chance that with this tek the pH is too low for the short term extraction to yield more even in the presence of polymerization. I'm hoping that the heavy basing alleviates this problem, but time will tell.

I imagine there is some kind of yield curve (assuming equal bark potency) that is described by:
1. ionic strength (largely driven by NaCL content in this experiment)
2. pH
3. time
4. temperature

And I feel we are very far from having any precise level of understanding of what that curve looks like. I hope to move us toward that

I'm not a chemist, so I could be far off base here.

Quick question, and sorry if this is derailing anything or if it has been covered already.

Is it possible that a larger polymer will lower the smell?

I ask as a result of my most recent extraction. Being unable to get my hands on distilled water, I decided to try regular filtered drinking water (though I have had perceptibly lower yields when using anything other than distilled; all the same Cyb mentions in the notes of the Max Ion tek why they (and apparently other chemists) prefer to avoid distilled water). I yielded 1.2% of DMT crystals that were much more yellow/orange than I usually get, and was also denser (I thought that there was maybe a half gram at most in the dish based on how it looked relative to past extractions with pure white crystals).

This batch has no smell whatsoever.

There was no gooey residue. Just DMT.

One love

Yellow yellow yellow

I have freebase from MHRB A/B that was done hot, and got lots of yellow/orange. While I believe it's "clean", I'm on a mission to obtain more pure white crystals and after reading a little bit on this thread, I tried doing backsalt with water + citric acid and then added heptane before slowly basifying all while <50°C and results are still yellow, although somehow they do look nicer to me than before (see below). At least it's all crystal and no oil, but am I correct that the yellow is from longer polymers of DMT?

One thing I'm doing that I wonder if it might play into the yellow, is I'm using Erlenmeyer flask and magnetic stir bar, with a rather vigorous vortex. I like the idea of guaranteeing that all of the spice gets maximum opportunity to transfer to NPS, but I'm wondering if the air (@ 45% RH) getting pulled into vortex is causing the yellow.

Thoughts?

Below is side by side comparison. On the left is from original A/B; on the right is after backsalt with citric acid and having heptane present before slowly basifying.

Looks like polymerization is occurring very slowly, if at all, in the base soup. Assuming this truly was a year long wait for pull 2.

https://www.dmt-nexus.me...spx?g=posts&t=102035

I too had seen not too much benefit from adding NPS before basing. If it does anything, it's not enough to considered a golden key to white. I think quick pulling is somewhat more successful, not letting the loaded NPS be too long in contact with the warm base. And heat of course, warmer is more yield but yellower. And maybe concentration too, if the base volume is small. I've had backwashes in small volumes giving oil at the bottom of the cooling to room temp NPS. My best guesses so far.