I am not denying that yellow cannot be dmt, and never have.

Some seem unable to admit that yellow can also be contaminated dmt.

Come on, get off the high horses, and down into the crystallization trenches, with some practical applications, rather than arguing about nonsense.

the only way to know that is with data.

speaking of data...that fantastic 2013 paper, the one of scanning calorimetric determination of polymorphs of dmt, did show certain solvents recrystallized dmt to a yellow, low-melting solid, particularly acetonitrile.

Thanks for the edit, but not good enough.

Perhaps do the experiment, decant an amount of loaded solvent with a few drops of the tar…look at the pics of dmt that some people post, it is not all pure dmt that is yellow.

What a ridiculous argument that yellow product is necessarily pure dmt.

that's not the argument....the argument is that the yellow color is not necessarily indicative of impurity. A pure dmt sample will turn yellow just sitting there, exposed to ambient air. It does that because that's an inherent property of indole, which also readily turns yellow, and eventually, ochre.

If we want to split hairs and claim it's impure because it's lacking some electrons, then sure.

there's also 'forced degradation'. applying heat, especially to certain solvents, accelerates oxidation (this doesn't mean N-oxide formation, it just means loss of electrons). A recrystallized product may turn yellow in this manner, and still have a sharp melting point, indicative of a highly pure product...and sensitive instruments wouldn't even be able to tell the difference between white and yellow crystals (which was the point of my experiments).

What I'm basically saying is that it's absolutely plausible for an impure product to have yellow color, and it's also just as likely for a pure product to turn yellow just sitting there...then the question becomes, is that product then impure? semantics. if highly instruments like a fluorescence spectrometer can't tell the difference..

I can/do/will provide data, and others should as well; consistent data leads to correlation. conflicting data just raises more questions. But, this is science, and it's independent on what I think/feel/believe, which is subject to change with supporting evidence.

Seems the hair splitting started, after i had already stated that both conditions were possible.

With direct assertion that I am “wrong”, then echoed by implied support for this assertion.

You still can’t seem to directly say, in plain english, that both conditions can exist. But, I’ll take it as so.

Now, can the obvious big guns of chemistry here actually deliver some practical info to improve the tek?

Maybe, How to significantly improve the maceration and pulling processes and reduce their time, while consistently delivering pure, WHITE crystals, at high yields.

This was posted while i was replying to your previous post.

I don’t appreciate the patronizing attitude, but thanks for at least going this far..

Now, to what you're asking about a tek that preserves that pure white color...that seems like a tall order. aside from complexing as as salt, I don't see any way to preserve the initial brilliant white color. This is quite likely due to the properties previously discussed; I postulate that the polymorphic properties, specifically how that terminal amine is oriented in proximity to the indole nitrogen, affects how readily that C3 on indole loses its electrons. A free base molecule has nothing to stabilize its structural orientation.

And I don't mean to patronize, I'm sorry if that's how you take my responses; I'll admit when I'm wrong, and I also admit that I don't know for sure, but my assertions are based on experimental data. I admittedly need more data to form a more concrete argument.

Here is some of that data, the same sample, white at t = 0, and orange at t = 6w.
The orange sample had larger peaks, because it was slightly more concentrated; but there are no extraneous peaks.

To preserve that initial lack of color, the best thing to do for a freebase, is to purge it with inert gas, and store in the freezer.

I accept your statement about your intent. You comments (as well as others on this site, at your chemistry level), here and in other threads, do come across to lowlings like me, as patronizing and smug, sometimes. I have experience in a number of “expert” cohorts, and this is very common when dealing with “non-experts”…something to be mindful of.

As far as “tall order”, wrt my “Maybe” comment (which appears not to be completely understood): it may seem so, but i think not.
For example, i think, and the literature shows, there are much faster ways to extract alkaloids from roots and lignified plant tissue. Yes, much of it is beyond kitchen chemistry, but if I had the appropriate chemistry background, i bet I could adapt some of this technology for our circumstances. An easier to defend example is Loveall’s work (as well as his humble approach, given his obvious expertise): he has already demonstrated significant pull process time reduction vs Max Ion (while maintaining good yield and WHITE crystals).

If you don’t set high, but achievable goals, you keep using old technology. I look forward to seeing some of the brainpower and expertise on this site, get back in the game of improving the extraction technology that was developed going on 10 years ago.

there's no doubt that some methods give the desired results more effectively than others. What I'm saying is keeping them in that desired state, in freebase form, is a whole other discussion.

I guess i don’t see the purpose of theoretical discussions that don’t provide practical applications on a site like this. My bad.

In practice, freebase definetly changes over time. This is a minor inconvenience for flame, but for sensitive and precise e-devices or e-juices tuned for fresh free base, it is a significant inconvenience for me (and I understand it may not be for others)

At some point it also becomes personal preference, not everyone prefers the same thing.

I personally really like e-juice aerosolized DMT salt. Near physiological pH it tastes mildly salty on the lips, not alkaline/numbing. Has great shelf life so far (not changing color like FB does). I'm leaning towards forgoing handling freebase altogether and simply moving towards a salt soluble in PG (like DMT citrate).

Thanks for the diversion, Loveall.

On my next Max Ion run, which acid, citric or ascorbic, and what pH range, would you suggest?

I've seen good results with citric around pH 4

Thanks

Sure, All white dmt can be yellow, but not all yellow dmt is white. Nobody is arguing that the yellow is always the result of polymorphism, this should go without saying. For example, if you have some dark yellow coloured naptha sitting in an extraction, you can be certain the color is coming from elsewhere..

The reason why some of us restate this is not because we're unwilling to believe it's something else, but because people tend to hyperfocus on these trival things and end up chasing ghosts when they aren't being guided by fundamental principles.

For example, any organic chemist can tell you that practically every pure organic compound which is white or colorless in its absolute pure crystalline state, is in practice, almost always off-white or yellow. Especially aromatic compounds, and even simple amines such as trimethylamine, colorless when freshly distilled, even despite best efforts to exclude oxygen and light, in no time at all reverts back to its classic yellow urine colour.

Now the budding chemist might be curious and wonder what is causing this, so he runs HRMS and proton NMR, except he sees no additional peaks, perhaps a slight broadening of peaks to the baseline.. meaning whatever this impurity is, its concentration is likely in the ppm range, and is considered negligible. To complicate things further, you have other effects going on that can contribute to the color change. This is why I said, to avoid pitfalls, color change first and foremost indicates a change in absorption, before anything else. After one begins to see this for virtually every compound he is working with, he becomes less concerned with the color, and more concerned with what the spectrometry is telling him.

It's not just theoretical, it's pragmatic. When you have the foundational principles guiding your thought process , you spend more time focusing on variables that matter ( solvent, temperature, concentration, etc) and employing the right techniques when they are useful, and so less time chasing ghosts. Even the best chemists make mistakes and chase ghosts, that's why it's often useful to re-evaluate what you think you know, your assumptions, and find out what you really know. This is what separates the masters from the beginners, because in practice it leads to success, faster problem solving, leading to successful reactions, higher yields, successful and fast purification, mastery of different techniqies and knowing which to use and why, especially in something like crystallization, this comes with the experience of dealing with many different organic compounds in various mixtures all with different properties.

You need to be specific. This is why you got in a spat with benzyme and got all defensive. What is "goos"? is goo supposed to mean just anything and everything that came out of a dmt extraction, no matter how sloppy it was carried out? Be specific. If it is goo that has some yellow black tar in it because you were sloppy in the extraction, then specify that. Then it becomes very easy to make the distinction where the impurity is coming from. Usually when people ask questions, its AFTER they followed everything that was neatly written for them in the cookbook tek. Otherwise I could have just as easily pissed on my crystal dmt and it would be equally yellow goo by your definition. So when someone posts 'what is my goo?' without being specific you have to basically assume that they could follow the tek and not spill any tar into it, because if they are asking the question why is my DMT goo you would hope they have at least covered the bases properly and not made any obvious mistakes that would account for discolouration or 'goo'.



Again, really?



Last time I checked, this thread was called Advanced/Enhanced chemistry » Polymorphic properties of DMT
not
Basic DMT Extraction help » Cheelin's extraction philosophy
Your 1-3 word posts are also bad mannered and not appreciated by anyone on the forum, since it forces people to click page after page to find the posts that actually have content.



have you ever heard the expression, give a man a fish, feed him for a day, teach a man to fish, feed him for a lifetime?

You've been here what, 4 months?

Its like your walking into a Michelin star restaurant, as a dishwasher on day 1. You ask the chef, "hey what do you think of my Bolognese? I tried this and that and it tasted like this." The chef responds not in the way you were expecting, instead of giving you a recipe for a Bolognese, he starts talking about things like flavor, fat and acidity balance, tasting the sauce and adjusting. And you hear that and begin to get frustrated "Why won't you give me a straight answer? why is he telling me all this esoteric nonsense why can't he just give me his recipe! He must be trying to guard it because hes smug!"

The problem is that you are looking for a new cookbook, the chef is trying to teach you how to think so you can write your own cookbook.

I listen to a lot of experts too in fields I am less familiar with, but I very rarely find them to be smug, very much the opposite. When I first joined this forum 12 years ago, benzyme was my senior and I didn't find him smug either. Actually the people who tend to be the most smug and conceited, are typically the ones who think they are experts but really don't know what they are talking about. They always eventually get found out, too. Loveall is a very smart and humble guy, but that is because he has an attitude which is the opposite of yours. He is always learning and he is always enthusiastic, he doesn't get defensive when he is wrong about something, he digs deeper so that he can understand it, he has good intuitions and knows his limitations, I admire him too.


Again, really? I'm still really struggling to find justification for such poor attitude. Sounds more like its coming from someone with a bruised ego because they fell off their high horse and is eager to get back on. Read the part again about the Bolognese.
---

Ok, back to polymorphs.

Here is some DMT (11g) that was extracted with ethyl acetate, and evaporated under vaccum.

It did not crystallize even when placed in the freezer for 48 hours.

On the third day, with the addition of a seed crystal, it finally began to crystallize into this amber colored mess. (picture 1)

I took this mess and dissolved it into 500mLs of boiling hexanes, I decanted from the residual insoluble (that is what is called an impurity). (picture 2)

The now colorless solution, was allowed to cooled, formed these dense solid crystals. (picture 3,4,5)

So clearly, the dmt here had some impurities, but it's origin was synthetic. An important thing to note, is that the impurities are not soluble in boiling hexanes, and neither would be expected polymerization products, although these are only trace impurities at best, in this case, less than 1% by weight. Thee crude product when it finally crystallized, appears different than the recrystallized final product, but without knowing about the x-ray diffraction study on dmt polymorphs, or at least by measuring their m.p. individually, I couldn't have said this. But it does serve as an excellent explanation for why the dmt did NOT crystallize even after sitting in the freezer for 48 hours, and being vigourously stabbed and scratched with a glass rod (as in, not supersaturation, but a m.p. depressed mixture of polymorphs)


I uploaded the 1H NMR spectrum of the above DMT sample, along with the 1H NMR of a MDxx oxime I was working with.

NMR can provide more information about structure than mass spec, but it has its limitations. Mainly in terms of sensitivity, you won't be able to discern anything useful below 1% of the primary molecule. If a molecule has interactions that change its structure in the solvent-phase, it will be apparent in the NMR spectrum, since we take the analysis when the sample is dissolved in some solvent (CDCl3). The oxime possess real rotational barriers that persist even at high temperatures, due to the N=O double bond, which results in the complex spectrum that seems like two different molecules. If we were to heat the oxime up enough to break the rotational barrier, we would see the separate peaks merge into a new single peak. In the case of DMT, in the solvent-phase, this rotation is so fast that it averages out to nothing, we see a single set of peaks. If this were solid-state NMR, and we were looking at each individual polymorph, then we would see some differences. But prior to the phase change, they are identical.