Thank you Jees. That all makes sense and you definitely helped me understand the goo a lot better.

Interestingly, after 1.5 hours in hot naptha (simply in a jar placed in boiling water) what used to be goo is now freeze precipitating as mostly xtals. At the begining of the process, for a few minutes some of the goo remained as a separate layer at the bottom of the naphtha before dissolving in (see image below). It is interesting that this layer (which looks like a candidate to decant from the hot naphtha) eventually dissolved and later on freezed as mostly crystals. Therefore, I think naphtha re-X can not only separate impurities from DMT, but when kept hot enough time, it may also break up DMT goo so it can crystalize better. I do not know how long this takes to complete though.

To summarize our preliminary findings:

1) Orange goo can be (and probably is) mostly DMT in a "condensed" or "polymer" form.
2) At high pH + high ionic strength goo seems to form and separate.
3) Goo can be broken up in acid water (exact acid type, temps, times needed are unknown).
4) Goo can also be broken up in hot naptha (needed time/temp unknown).
5) Goo is less readily soluble in naphtha than crystals.

So perhaps to change goo to crystals: a long acid boil, not being too aggressive with the base/salt, and keeping the pulled naphtha hot before freezing could all be beneficial.

Since DMT is in salt form in the plant, I don't think it would start as goo. However, it could become goo during the basing step. Perhaps choosing the base condition carefully (pH and ionic strength not too strong) and minimizing the time spent in the base could be ways to avoid the goo to begin with. Making the naphtha pull hot for some time before freezing could break up goo formed in the base step.

I'm not sure about the zinc. At this point it does not seem needed. Would be interesting if it did something in tests.

Another alternative that is testable would be to add some acetone to the naphtha, it may help break up the goo and not interfere too much with crystalization (I remember benzyme mentioning acetone worked pretty well).

I'm not going to extract very soon, next time I will address it differently. That goo'ing batch of this thread sat many many days in STB lye, not going to repeat that.
Lysing bark/cells can also be done in strong acid instead of lye.

I wonder how much potent material has been thrown away by individuals doing reX and finding all that 'alleged gunk impurities' at the bottom.


Another thing crossing my mind:
I remember reading one of the home chemists here washing his loaded naphtha first with water/Sodcarb to get all base accents out, but then also ran the naphtha over magnesiumsulfate, then went to freeze precipitation.
This drying of the naphtha got my attention and I wonder if the long naphtha boil is just doing the same namely cooking out the assimilated water. Suggested mechanism: the low partial pressure presence of water in this case lowers it's cooking temp enough for this to happen in boiling naphtha (in analogy of industrial oil refineries). If so then a cook with a lot of reflux (semi closed vessel) would be counterproductive to rid of the water.

Hydrocarbons can hold a tiny amount of water [see attached pic] without separating and I'm wondering if that could interfere with the precipitation characteristics of deems.
If you pull warm the solubility of H2O in HC rises, going from 20 to 40 degC it's like X3 for hepthane, I used to pull at around 40degC.
By cooling off, the water seeks to drop out of the HC simultaneous with the deems, do they marry to make goo???
Dunno if a pushed far up water pH would skew this solubility in HC even higher??? The lye-water experiments lean in that direction anyway, this could be coincidental.
The exercise would then be to compare a naphtha MgSO4 treatment to a naphtha boil.
I'm just freewheeling some thoughts here, if it's nut's please chime in, perhaps the numbers of solubility are of a non-issue at all?

Pic from here. Dunno about larger aliphatics.

I remember fiddling with some goo many years ago. It was during a recrystallisation of freeze precipitated crystals in light naphtha. An orange goo separated on dissolving most of the very pale apricot yellow crystals. On heating the naphtha to about 60°C, the goo would dissolve, causing a noticeable darkening of the solution. Some, but not all, of the goo reprecipitated on cooling to around 40°C.

The yellowish solution was pipetted off and a small amount of new warm naphtha was added to the remaining goo, which again dissolved on heating to around 60°C. I recall having repeated this a few more times with ever-diminishing amounts of goo and feeling baffled that the 'contaminants' didn't seem to be getting any more concentrated.

If only I had kept better notes back then, but that's the general gist of it.

All-in-all, it seems to indicate some validity to the polymerisation hypothesis.

Thanks DFZ, makes sense.

Jees, for what it is worth, I once tested magnesium sulfate to thoroughly dry naphtha before freezing but did not notice a significant difference in the final product.

Here are two pictures from some of the earlier discussion above as reference.

First picture: Orange goo from an A/B extraction (pH above 12, and NaCl used to increase ionic strength). How I got 3 jars: Warm naphtha pull was allowed to cool to room temp. As this was happening clouds formed and eventually a thin orange layer appeared at the bottom. This was decanted off, but the same layer settled on the new jar. This was repeated until the red layer stopped appearing. The decanted jars are shown in the picture.

Second picture: Goo from all jars was dissolved in vinegar and combined. Vit C and citric acid were added to this and it was left to stir overnight. Quick A/B was performed (no salt was used this time) and fluffy white-ish xtals formed upon freeze precipitation (image taken after pouring off naphtha). There is still a little off color (light yellow towards the bottom). That could be some remaining DMT polymer that crashed out first (or something else of course).

What I will try during my next extraction is to be quick during the base step and back off on the pH and ionic strength. Also, will add a new step where the naphtha is kept hot for a couple hours before freeze precipitation. Maybe all this put together minimizes DMT in goo form.

Not that the goo is necessarily a bad thing. It is just difficult to handle and also difficult to distinguish from non-DMT stuff if any of that comes through. It has been said many times that goo is fine as is, we are just wanting to understand what determines if DMT decides to show up as humble sticky goo or in fancy designer clothes (aka crystals). This is something I think we all agree on (and dozens of nexus threads discuss), just making it explicit here too

I'm now wondering about extractions that also have NMT (like acacia). Not sure if NMT can crystalize/polymerize too, but if it does, the modulators we are exploring here may be relevant.

Here are the pictures for the 1.5 hours of hot naphtha (jar in boiling water) treatment of the goo. 1st picture is starting goo, second picture is freeze precipitation result. Not as impressive as the overnight acid treatment with stirring from the previous post.

I'm going to try low heat hot plate stirring of naphtha next to see if the conversion from goo to xtals is better.

Benz, how sure are you about the polymerization occurring in the solvent? From what I've seen supersaturated solutions of DMT/naptha don't polymerize and can grow very large xtals when evaporated slowly (see example below). Also, stirring and heating goo in naphtha alone seems to break up the polymer goo (preliminary results).

However, I don't have experience with evaporating other solvents with DMT (e.g. acetone).

On the other hand, we have some evidence of polymerization during the basing step. Looks like we can even get concentrated DMT to separate out as a layer above alkaline water of high ionic strength. Would it make sense that in such conditions DMT free base would want to group together surrounded by ions?

Thanks!

There goes my suspicion about assimilated water in hydrocarbons being a culprit here, thanks for narrowing down

Maybe there is also some polymerization when heating your stuff while vaporization. Even if you use no open flame, a brown residue may remain, even if the starting material was plain white. This residue will also not vaporize any further, even if heat above 250 °C is used.

So is the idea that if there is un-vaped melted spice, some of it will form a strong polymer while cooling that will be more difficult to vape at the next session?

I think that makes sense. It would explain something that has always puzzled me about my personal crafty use. I typically load it with ~150mg of spice for several sessions spread over time. After a few sessions, effects stop, but when I clean it, there is still stuff in the heat chamber that dissolves in IPA. I wonder if I could turn that back into vaporizable stuff with the methods discussed here.

Also, this proposed "hard" polymerization in my crafty takes several heat/cool cycles to complete. After the first heat cycle all the xtals melt and become goo soaked into the stone, but that still vaporizes later on. However, after several heat/cool cycles it stops vaporizing even though there is some still left (based on observations during the IPA clean). Empirically I've been increasing the temp setting for the later sessions to get the same effect. I assumed that the increased temp was because there was less spice, but more importantly, it could be that I was unknowingly adjusting for the degree of polymerization increasing with repeated heat cycles.

More speculation: I'm starting to think that maybe there are several "degrees" of polymerization. xtals would be the easiest to vaporize, then goo that is almost xtals, then goo that is closer to more complete polymerization, and then eventually heavily polymerized DMT that is very hard to vaporize. If this is true, it could be causing us some headaches when comparing low temp device settings such as e-mesh (see am example below for the big swings in melting temperature vs polymerization for polyethylene from Wikipedia - illustrative only DMT may be different). The older flame devices (GVG) would be more robust to polymerization (just bring the powerful flame in a little closer by hand).

CYB's max ion tek is interesting because (as I understand it), it dilutes the DMT with a liter of 8% salt water before basing it. I always thought that was just to later get the naphtha up to the neck of the bottle so it is easy to remove, but now I wonder if limiting to ~8% salt strength (+added vinegar/lye) also helps avoid polymerization during the basing step. As mentioned earlier, both Jees and I saw oil (DMT polymer candidate) during the basing step that gave a from milky white liquid (very high ionic strength, high pH, and "high" DMT is concentration (~1g DMT in 100ml as a guestimate))

I fear that I may have thrown away a lot of recoverable DMT over the years because I was not aware of the potential nuances around polymerization.

I've also noticed that when trying to get-it-all the last of a hit makes for a tad blue-ish smoke compared the very white smoke in the beginning, glass pipe indicating. And it starts to taste more too in the throat, even without harsh burning it gradually seems to slope into that direction and have me thinking when to stop, I rather not have to bother at all during inhaling. This promotes the idea of changa where all of that is a non issue.

Jees, what NaOH concentration do you use? NaOH will add its own ions and contribute to ionic strength. From an ionic strength point of view 10% NaOH is equivalent to ~15% NaCl.

It's unmeasured actually, dripping in 8mol lye-water drops until the pH paper (max 14) goes out of charts , so you have a point there I had't considered, it's pretty NaOH stiff. That plus some salt from the neutralization of the acid at first.

Benz, I think Jees and I are also seeing evidence that polymerization can occur over time in basic water at high pH (or high ionic strength) and high DMT concentration.

Perhaps all extractions have some degree of DMT polymerization while basing? Maybe it can be minimized by managing these factors (?).

Related:
https://www.dmt-nexus.me...aspx?g=posts&t=53101

Thanks Jess. In the paper that dreamer042 posted they found two forms from re-x crystals. I think we are seeing more forms beyond that (orange oil). I don't think that in the paper that potential DMT form was analyzed based on how they got/sourced their material. I think we showed here that the orange goo is another form of DMT by converting it back to xtals after an acid treatment.

The orange DMT oil can be separated out during re-X since it takes longer to go into naptha and also crashes sooner (I've seen it fall out from naptha at room temp before freezing). I fear that this DMT is being lost systematically many extractions. I think the researchers in the link above never got their hands on it to begin with.

For completeness, this is how the researchers sourced their natural DMT (from reference [15]):



They used about 2L of solution for 60g of bark with gentle pH and NaCl concentration of 0.1M (~6%). This is more dilute and gentle than any tek I know, perhaps the closest one is Max Ion with ~1L for 100g of bark, NaCl ~ 10%, and pH ~ 12. These gentler conditions seem to avoid the orange goo formation and may give higher xtal yield. In my experience, a more concentrated, high pH, high NaOH, high ionic strength tek will give a lot more orange oil and less white xtals. Since the orange oil is less soluble in napthata, warm pulls are needed to pick it up, but it is perfectly good stuff.

I think you're right, their main focus was determining of 2 polymorphs in the crystal form with distinct melting temps, no matter dmt-source or solvent used.

However in their course of preparation re-X stage they encountered the famous yellow bottom layer to exist (not going into solution) in warm hexane of 45degC.
Cool to see affirmation of the bottom layer of Re-x is here considered "pure DMT" and hence should not become discarded (if it's free of contaminants like carried over base).

What they found as that yellow layer in 45degC warm naphtha, I suppose it is the same stuff that we've seen crashing out at room temp before Re-X and what we're trying to get back in crystal form. Do you think it is the same too?

Yes, I do. Thanks Jees.

I take this back. Marco-molecules are common in biological systems. It is very possible that DMT is aggregated in the plant. Even in salt form, it could form a sphere with indole rings weakly bonded together in the center, and + amine charges in a shell ionically bonded to large biological cations. I have no direct evidence for this type of structure, just made this up to point out that something like this could be a possibility.

If so, the acid step is important to break down any naturally DMT aggregation and minimize goo. Perhaps acacia's have a higher degree of natural DMT aggregation, causing more oily DMT during extraction unless an aggressive acid step is done (see Northerner's important acacia result).

To complicate things further, the basing step can also aggregate DMT into goo.

I think managing DMT aggregation could improve DMT extraction and make it more reliable/predictable. It could be an important variable that has been mostly ignored/overlooked.

You are onto something here. There is a bunch of research around indole aggregation and how it affects emission. People are thinking of using it for color applications. Attached is an example paper. Image is the calculated dimer structure for several indole derivatives.

So yeah, DMT is very likely to aggregate. Explicitly breaking down to monomers and keeping it as a monomer could help control the extraction process.

Those photos are telling!

In second photo below it appears that a seperation is going on forcing the dmt to be super purified!

great work...