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DMT Molecule Smokes Changa and Laughs at Me

Migrated topic.

mikeAtHome

The only God I can imagine is a God that I can't p
Hi all.

I’ve just read a mind-blowing article about the DMT molecule that I wanted to share with you. I’ll summarize the findings and try to explain what certain procedures mean to save you time from having to read the entire article yourself and then research what certain sections mean. But first, I’m going to provide a preamble and if you get bored reading it then just jump right to the source (and spend even more time dealing with that). But here it is in case you want:

Investigations into the polymorphic properties of N,N-dimethyltryptamine by X-ray diffraction and differential scanning calorimetry


(this link works for me but I don’t know if it’s because I created an account or not, I can’t remember. If I did need to create an account, I guarantee that its free or I wouldn’t have done it.)

First, I need to come clean. I am a new member here and got most of my practical chem knowledge from the abundance of meth forums on the Internet. I spent a long time and never talked to a soul. Not because I’m shy, because all the threads and info were over 10 years old (more like 15). Nobody in the USA makes meth any more except for a few hobbyists and those able to steal lab supplies. If you look on the dark web, there are a good number of meth sellers but I’m pretty sure all that stuff is coming in via Mexico.

Meth chemistry is very interesting, especially as it developed over the years. There were tons of ways to synthesize it from easily obtainable sources. Then chemicals started getting regulated which drove down the number of reductions available. Towards the end of the meth craze (around 2003-2004) most folks were using OTC allergy meds as their precursors and doing reductions in one of 2 ways. What is interesting is in the way home chemists had to constantly keep up with new junk manufacturers were putting in their pills to prevent the isolation of the precursors. So you would wind up having to do many extractions before you could reduce and then extract your product from the freebase that the reduction left you with. The extractions were mainly targeted at pulling out contaminants. Some extractions were to extract precursors that would be used to create precursors that you needed for the ultimate reduction. It got very interesting.

While DMT can be synthesized many ways, I don’t hear of them around here, only extractions of the natural product. That’s fine. Even if I could get my hands on the precursors I’m not nearly talented or brave enough to perform a messy synth. What struck me as odd when I came here was a perceived lack of drive to perfect these extractions. When meth started getting tough, I saw everyone scrambling to identify the latest contaminant and a way to target its elimination. Yields got very important. Here, yields from bark range from under 1% to over 5% - and that’s just for MHRB! And within those extractions that used the same tek on the same strain, there were all these different results: different colored spice, spice just melting away, emulsions and so on. And nobody seemed very interested in getting to the bottom of it. I even saw one post on another forum to a guy who had just done his first extraction, managing like 0.3gr from 50gr MHRB. He had no idea if that was good or bad and could have cared less. When someone posted some advice that could possibly increase his yield, his response was, something like, “nah, that’s okay, I like the way I’m doing it.” The DMT world is so laid back when it comes to perfecting yields that it was driving me crazy. Then I read this article and all became clear.

One last thing before the article summary. I probably shouldn’t even have an opinion on this because I’ve never even performed an extraction. But I felt from the beginning that hexane (and that’s not the same as heptane) might make an excellent solvent for STB (I also think STB makes way more sense than A/B but that’s another story and again, I don’t have enough experience to be committed to that opinion but think I could provide a reasonable defense for it). NAPTHA’s inability to commit to being a solvent unless it’s warm works to the advantage of A/B. Not so for STB. I did find some validation about hexane out there on at least one other forum. And still other forums trash talking NAPTHA in favor of toluene. Opinions abound. This article makes use of hexane in a STB and nothing terrible happens. So let’s get to it:

Some background terms:
Amorphous/Polymorphous” molecular behavior, “DSC”, “Heat Capacity” (or Cp for short) and “Phase Shift.”

What “Polymorphous behavior” refers to is a compound's propensity of going from glass-like in structure to crystal-like (and back). The opposite behavior is “Amorphous” (compounds arrange their molecules in a particular pattern and stay that way). Phase Shifting is similar but refers only to the natural changes that happen to any element when it changes “phase” – liquid, solid and gas etc. We usually attribute phase change to changes in temperature. So if a compound is polymorphous then any particular sample of that compound can change phase (melt, crystalize, whatever) at a temperature that is different from other samples in the exact same compound!

As for the remaining unexplained terms:
Differential Scanning Calorimetry, or DSC, is a thermal analysis technique that looks at how a material’s heat capacity (Cp) is changed by temperature. “ I.e. how much heat is required to raise a compound’s temperature and by implication the heat required for a phase change.

One of the article’s quotes might refer to a Fast Scan or Fast DSC. That’s just a DSC that changes a compound’s temperature very fast. They do this because it fast-tracks a polymorphous compound’s inclination to shift to a new phase.

Okay, here’s what these guys did.

Actions Taken

#1. They created samples of DMT by way of synthesis and plant extraction. The extracted DMT used hexane via STB .

#2. Then they ran two Fast DSC’s of varying temperatures. I think they stashed some samples away without running any DSC on them so they could experiment with other ways of getting a sample to have a particular polymorphous property that was not the result of a DSC. For the samples that did get a DSC, the DSC did cause a change in polymorphous behavior. But other things could also change that behavior as you’ll see. Polymorphous compounds are weird not only in that they do that glass/crystal thing but they also change in other particulars like Cp, melting point and even color. The bottom line is that the two DSC’s created two more divisions among the sample for the authors to observe with the primary difference being different melting points.

#3. They re-crystallized some samples using hexane and all other samples with a different solvent called acetonitrile. Again, a sample’s method of re-crystallization was independent of how the sample was treated in #1 or #2.

So you have 3 different treatments going on and any particular sample could be the result of any combination of those three treatments. What they saw after re-crystallization is that the DMT re-crystalized with hexane had white crystals and the other samples had yellow crystals. In other words, just using a different solvent for re-crystallization had an effect on at least on polymorphous property.

This was getting confusing but they finally decided to create three named binary categories for the samples:

“…samples W1 and W2 were predominantly white crystals obtained using crystallization from hexane; whereas yellow DMT samples Y1 and Y2 were obtained following crystallization with acetonitrile. Samples W1 and Y1 were crystallized from DMT prepared by organic synthesis, while samples W2 and Y2 were from DMT isolated from the bark of M. tenuiflora.”

And then:

“…the higher melting polymorph was deemed Form I whereas the lower melting polymorph was termed Form II.”

Here what they discovered and concluded: (I’m not bothering with the quotes because I’ve condensed and re-worded a little):

-The samples with the lowest melting point encountered were described as a pale amorphous solid that melted at 38 °C–40 °C. At the other end of the spectrum were samples with a melting point of 47 °C–49 °C following its synthesis and recrystallization from hexane. Interestingly, the authors then mentioned a conversion of this sample to a form with a higher melting point (71 °C–73 °C), also by recrystallization from hexane, by seeding with an authentic sample with a melting point of 73 °C–74 °C, respectively.

-They confirmed the prevalence of Form II in this sample compared with DMT W1 and that again it converted to Form I at the slower heating rates.

-They confirmed the apparent higher ratio of Form II in sample W2.

-The recrystallization to Form II in DMT W2 was not as easily accomplished as in DMT W1.

-One attempt to obtain pure Form 1 was by heating the untreated samples to 45 °C and holding the samples at this temperature for 20 min to allow conversion of the Form II in the sample to Form I, prior to cooling and then re-scanning at 2 °C min− 1. The approach indeed worked

-DMT Y1 and DMT Y2 were both yellow and appeared denser and less crystalline.

-DMT Y2 displayed an increased prevalence of Form I in the sample at 100 °C min− 1. Indeed, at 2 °C min− 1 there was little evidence for any melting or conversion from Form II to Form I.

-They confirmed that DMT Y2 initially was the most amorphous of the samples and contained the highest level in Form 1 of DMT.

-They were able to confirm the apparent instability of the Form II of DMT (those were the samples with the low melting point and hence judged instable, I suppose).

Conclusion

The data provided in this paper have shown that DMT can be recrystallized from the solvents hexane and acetonitrile to give crystals that are a mixture of two polymorphs. The fact that two clearly exist explains the variation in melting points reported previously in the literature. It seems possible that use of the latter solvent gives crystals with a greater amorphousness and a yellow coloration. This solvent dependency was independent of the source of DMT.
The data thus suggest that this was solvent-mediated through increased amorphicity in the sample rather than a specific solvent–DMT interaction.

The data provided in this paper have shown that DMT can be recrystallized from the solvents hexane and acetonitrile to give crystals that are a mixture of two polymorphs

One attempt to obtain pure Form 1 was by heating the untreated samples to 45 °C and holding the samples at this temperature for 20 min to allow conversion of the Form II in the sample to Form I, prior to cooling and then re-scanning at 2 °C min− 1. …this approach indeed worked …

And as for yellow DMT…

“...was solvent-mediated through increased amorphicity in the sample rather than a specific solvent–DMT interaction.”

Well that’s about it. DMT is a crazy molecule. I can’t change its mind about any particular property for just about any reason it wants. I’m not sure what the actionables are. If we don’t want a low/unstable melting point does that mean that we shouldn’t switch solvents midstream, or that we shouldn’t use acetonitrile to re-crystallize or that we should use hexane or none of the above?

I liked that last comment about the yellow crystals not being caused by the solvent but by a change to “amorphicity” brought on by the solvent. I've heard so much about mysterious yellow crystaks that seem to pop up out of nowhere in someone's extraction. The question has veen anwered: THERE IS NO ANSWER!

And that's why DMT laughs...
 
mikeAtHome said:
(this link works for me but I don’t know if it’s because I created an account or not, I can’t remember. If I did need to create an account, I guarantee that its free or I wouldn’t have done it.)

No account needed, PDF was downloaded without any issue.
 
DMT polymorphism has been covered pretty extensively here. You can find discussions on it here, here, here, and here, and those are just the top search results, with the topic coming up in numerous other places as well. 😉

I saw in another post of yours that you're having difficulty with the site search engine (it's not so great). Instead try googling the following [the thing you want to search] site:dmt-nexus.me, like this

I think if you look through this site, you'll find quite a few (successful) attempts at procedural perfection. Hell, you can even find the full conceptual breakdown that should allow for maximizing yields by ensuring thorough understanding of what you're actually trying to do. There's really no need for synthesis, especially given the issues commonly encountered there and considering the fact that you can grow your own source material.

As far as 1%-5% yield claims, mhrb inner rootbark provides a pretty reliable 1.5%-2% yield. Significant deviation from that range generally indicates something else is going on. This has also been covered in numerous threads. This is, generally speaking, an entirely different issue than the one of polymorphism.
 
sorry i didn't read the article yet but i couldn't find where they mention the over 5% yield from extraction can you please show us where they mention it?
however i found this
Following the implementation of liquid–liquid extraction using 60 g of powdered inner bark of M. tenuiflora, 421.4 mg of crude alkaloids (0.7% yield) was obtained from a concentrated hexane layer at 4 °C [28]. The majority of crystal material was white in color but spots of yellow-colored crystals were also observed. In order to carry out a recrystallization from hexane the total amount of crude alkaloids was re-dissolved in 10 mL of warm hexane (45 °C) which led to the formation of two distinctly colored layers. During analytical characterization (data not shown) it was found that both layers contained DMT where the bottom layer (yellow in color and minor in abundance with regards to volume) represented an amorphous, high density, and viscous form of pure DMT. The top transparent layer consisted of DMT dissolved in hexane. The transparent layer was removed and stored at − 18 °C which led to the formation of white DMT crystals (181.0 mg, 0.3% yield). Storage of the yellow layer in the fridge at 5 °C produced a yellow amorphous solid which was not investigated further.
so just 0.7% yield of crude alkaloids???
 
My bad. The error has been corrected. It was getting late and I must have took the .7 for 7 (I just checked the article source). The reference to the extraction is on page 147.

But you did have the correct article. That website is an fun resource if you like that sort of thing. It's not overly obvious but when you follow the link, you wind up seeing the abstract. And just on top of the title, a little to the left, there's a link to download or view the PDF version.

Anyway, I shouldn't have got so stoked but the authors seemed very excited so I sort of caught the flame. Then when I was browsing for more general articles on polymorphous materials, I came across an article on that very behavior in pharmaceutical small-molecule compounds. I soon learned it was no big deal in general and maybe even more the rule than the exception when you put that restriction on it. But while polymorphous behavior isn't all that unique it also tends not to cause a lot of trouble when it shows up. So they were also talking about how often that happens and it's not that often.

Looking at some other alkaloids in the same group as DMT, I found a couple 'shroom alkaloids that were and I think ergotomine or whatever (the precursor for LSD) is also. And I didn't have to do mucdh searching. Duh.
 
SnozzleBerry said:
DMT polymorphism has been covered pretty extensively here. You can find discussions on it here, here, here, and here, and those are just the top search results, with the topic coming up in numerous other places as well. 😉

I saw in another post of yours that you're having difficulty with the site search engine (it's not so great). Instead try googling the following [the thing you want to search] site:dmt-nexus.me, like this

I think if you look through this site, you'll find quite a few (successful) attempts at procedural perfection. Hell, you can even find the full conceptual breakdown that should allow for maximizing yields by ensuring thorough understanding of what you're actually trying to do. There's really no need for synthesis, especially given the issues commonly encountered there and considering the fact that you can grow your own source material.

As far as 1%-5% yield claims, mhrb inner rootbark provides a pretty reliable 1.5%-2% yield. Significant deviation from that range generally indicates something else is going on. This has also been covered in numerous threads. This is, generally speaking, an entirely different issue than the one of polymorphism.

Yeah, I could have done more research before that post. But to be fair, it was an awfully long article and the authors' enthusiasm really did rub off.

As soon as I posted the question about the site's search functionality (which is working fine now), I saw the post on how to use Google as the search engine. I now have all 3 search URLs as browser bookmarks and use them exclusively. So while I'm a little thick sometimes, I am trainable. And before anyone else brings it up, I take everything I said about hexane back. Not the worst choice in the world but pretty bad when targeting alkaloids (mainly).
 
mikeAtHome said:
...What struck me as odd when I came here was a perceived lack of drive to perfect these extractions...
That was a hot sentence :twisted: .
My thoughts were like: "Oh this person is going to teach us how to do things properly and we'll go home with double a yield." Of course I knew that was not going to happen 😁
There could be unfair comparison between MHRB and acacia if the latter it's NMT is considered yield also. For the rest 2% DMT looks like a good works done, I'm usually tad below :oops:
BTW source material differs too, cannot count tek responsible for that one.

Glad you come around fast mAH, and I too should learn more to compile a post, let it rest, re-examine, edit, post it later. This practice saves a lot of vortexes in the forum, I am mostly telling myself here ;) Just sharing.
 
Jees said:
mikeAtHome said:
...What struck me as odd when I came here was a perceived lack of drive to perfect these extractions...
That was a hot sentence :twisted: .
My thoughts were like: "Oh this person is going to teach us how to do things properly and we'll go home with double a yield." Of course I knew that was not going to happen 😁
There could be unfair comparison between MHRB and acacia if the latter it's NMT is considered yield also. For the rest 2% DMT looks like a good works done, I'm usually tad below :oops:
BTW source material differs too, cannot count tek responsible for that one.

Glad you come around fast mAH, and I too should learn more to compile a post, let it rest, re-examine, edit, post it later. This practice saves a lot of vortexes in the forum, I am mostly telling myself here ;) Just sharing.

Amen to that. Hope you don't mind me editing the font on your quote above, just wanted to emphasize the particulars of what I was saying the "amen" to. Not that I take issue with anything else.

The fact that DMT comes from plant matter that was harvested some random time in the past and grown in a variety of environments makes a huge difference in what everyone around here much go through. As in having all supplies being fairly fresh and coming from nice stable molecules spawned in a sterile lab environment. I did not come even close to understanding this when I arrived. Doubt I'm there yet.

It would have been so much easier exploring this area a few decades ago when chemicals and plants had not yet been banned. And whatever it was that you were after probably wasn't even illegal!

Maybe in another life...
 
mAH your remark that people get a wide range of yield hold truth after all, even when given them all the same source material. I think it is inevitable to miss out on actives and it would be best to aim for best yield possible, if not only out of respect for the plants that gave the material to us. There is no verifying if the 'middle man' claims sustainable processing. You are right, people better aim for best yield.

Someone asked The Traveler once: What is the best tek?
One would think automatically the best yielding one.
Yet other considerations might interfere with the choice of tek:
* what access do you have for acid, base, solvent ...
* what equipment is available: glassware, fumehood, must it all look un-suspicious or is lab-alike no problem (e.g. separator funnel);
* do you live in an apartment where smell is a problem, or not;
* is available time a factor?
* some people only want to work with food safe components;
* does one want white crystals only or satisfied with yellow and perhaps goo;
* for acacia: you want the NMT out or comprised in the end result?
* is operator sort of clumsy or chem handy?
So it's possible a lower yielding tek is forced on by circumstances.
For myself I've never found myself doing things twice exactly the same, there's always that curious: "What if I do this now like that?" 😁
Sometimes not the best attempt was made in hobby wise fiddling about. Yet for others with more restrictions better follow a given tek down to the T. So many things play a role when it comes to what procedure to follow. The wide library in wiki might serve as an illustration of possible variety for different strokes.

:thumb_up:
 
mikeAtHome said:
My bad. The error has been corrected. It was getting late and I must have took the .7 for 7 (I just checked the article source). The reference to the extraction is on page 147.
yes that's what i realized later 0.7/7

mikeAtHome said:
Anyway, I shouldn't have got so stoked but the authors seemed very excited so I sort of caught the flame. Then when I was browsing for more general articles on polymorphous materials, I came across an article on that very behavior in pharmaceutical small-molecule compounds. I soon learned it was no big deal in general and maybe even more the rule than the exception when you put that restriction on it. But while polymorphous behavior isn't all that unique it also tends not to cause a lot of trouble when it shows up. So they were also talking about how often that happens and it's not that often.
check these beautiful rectangular DMT crystals, the polymorph fish caught, also check the whole thread if you haven't before it's amazing

mikeAtHome said:
Looking at some other alkaloids in the same group as DMT, I found a couple 'shroom alkaloids that were and I think ergotomine or whatever (the precursor for LSD) is also. And I didn't have to do mucdh searching. Duh.
i'm not sure what the "same group" means but these alkaloids and others like harmalas alkaloids, ibogaine and many others(the good kind of drugs :p) share "the indole ring" which i find very interesting
 
Saakkadelic - thanks for the links. Those xtals are beautiful. And he's going to reX 2 more times to purify!

What I meant by the same group.... what difference does it make? There seems to be at least 3 or 4 popular ways and there could be more. I'm not really all that sure which group. I'm not even sure if "group" is the correct term. It's confusing as hell not only because of the different taxonomies - historical, functional, genetic i.e. had the same amino acid pair and I read that they can also grouped by a combo of function/genetic. But those are broad strokes because there's all the sub-categories and sub-sub etc.

At least they are both Indoles. In one scenario, aren't they also in the same functional group. And they have one parent amino acid in common. I know you know this 'cause you've been a member for so long. When it comes down to grouping alkaloids, what to do? So I was thinking that grouping by functionality, you get DMT and ergotomine in a fairly tight knit group. and might as well throw mescaline in their too since it's polymorphic as well but no Indole. Which is really the reason I didn't mention it.

Wiki. also has a "Chemical Grouping" one if which is "Tryptamine alkaloids" and that throws DMT and Tryptophan in with Psilocin and Psilocybin. I guess you could probably find some grouping somewhere that had any 2 alkaloids you wanted.
 
Sakkadelic said:
mikeAtHome said:
My bad. The error has been corrected. It was getting late and I must have took the .7 for 7 (I just checked the article source). The reference to the extraction is on page 147.
yes that's what i realized later 0.7/7

mikeAtHome said:
Anyway, I shouldn't have got so stoked but the authors seemed very excited so I sort of caught the flame. Then when I was browsing for more general articles on polymorphous materials, I came across an article on that very behavior in pharmaceutical small-molecule compounds. I soon learned it was no big deal in general and maybe even more the rule than the exception when you put that restriction on it. But while polymorphous behavior isn't all that unique it also tends not to cause a lot of trouble when it shows up. So they were also talking about how often that happens and it's not that often.
check these beautiful rectangular DMT crystals, the polymorph fish caught, also check the whole thread if you haven't before it's amazing

mikeAtHome said:
Looking at some other alkaloids in the same group as DMT, I found a couple 'shroom alkaloids that were and I think ergotomine or whatever (the precursor for LSD) is also. And I didn't have to do mucdh searching. Duh.
i'm not sure what the "same group" means but these alkaloids and others like harmalas alkaloids, ibogaine and many others(the good kind of drugs :p) share "the indole ring" which i find very interesting

Yeah Jees, I wouldn't expect folks to be getting the same "yield" even using identical Spiecies and tek. With lab-made chemicals you know the exact composition of the mass you're extracting from so "yield" has a very well defined meaning. But since we never know how much DMT is contained in the mass (be it root bark or powder) and tend to state yield as "for this spieces, I extracted x grams from y pounds." I don't think anything better can be done and it's a shame 'cause the highest true yield tek could easily get over looked. Out of all the digging I've done on the DMT Nexis Wiki, I never saw any log of tek, species/format, input weight and %yield (loosely defined). It would be helpful to have that info but a PITA to keep current. As a hobbyist I would never expect the same percentage yield as the folks going after 15 times more end product. You can't match that no matter how diligent you proceed.
 
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