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The BIG Analysis on DMT(s) [1H-/13C-NMR/HPLC/LC-MS] Options
 
Mindlusion
#21 Posted : 1/24/2019 3:18:06 PM

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Brennendes Wasser wrote:
Uh well maybe I overdid a bit in this calculation - of course there is a detection limit in the low mg range and if 100 mg were used for the measurement and we have some compounds with 0,1 % - 1 % content it will be hard to impossible to track them with NMR.

That point of retrieving the purity just by dividing the foreign peaks with the Spice peaks and counting all decimal places is not that correct, thats also a good point Rolling eyes .

Well this is from the Internet:

Quote:
The Minimum Detection Limits (MDL) for proton measurements were in the range of 3-10 µg/g. The quantitation accuracy for purity determinations was measured to be in the range of 1% relative to an internal standard. Specific MDL values should be determined for each particular matrix, internal standard, and instrument conditions.


Ok I should give up on the former number ...

But I still claim that the results are interesting, showing that you can get 99 % + purity directly from the bark Wut?


Of course, don't get me wrong this a great thread. I've come to check it for reference a few times now. Good work here. A similar experiment was done by endlessness and others with mass to show that crude spice from mhrb was still mostly DMT, >98% or 99% in most cases, and that hexane re-crystallization or freeze precipitation to yield white crystals gave a very pure product. In fact this is universal for a lot of synthetic tryptamines, which is very helpful in cleaning up a crude without the use of column chromatography.
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Loveall
#22 Posted : 1/24/2019 4:17:21 PM

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Yeah, significant digit higene is an important part of reporting results.

Now excuse me while I prepare a tea with 32.34527942956328532582456734103957257295 grams of fresh mushrooms and 208.56743228102847274929402742747 ml of water. Big grin
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benzyme
#23 Posted : 1/25/2019 5:13:11 AM

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it's nothing that hasn't already been done..
these cats have been consistently getting crystals that match up with Cerriliant purity, spectra and all.

unless you're running an instrument like a Lumos Tribrid, you won't get ultra high res. My mentor once said, "NMR is for cavemen."
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Brennendes Wasser
#24 Posted : 1/25/2019 4:39:00 PM

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Quote:
it's nothing that hasn't already been done..


I dont find anything of this here - maybe there is some HPLC Stuff, but of course with NMR (+ HPLC + MS) there is a much deeper insight.

Also I havent read about cats that posted their spectra of their crystals, I guess those spectra here are the first.

Quote:
NMR is for cavemen


Confused Rolling eyes Big grin
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
benzyme
#25 Posted : 1/25/2019 6:03:15 PM

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we (bufoman, burnt, and myself) posted GC-MS and LC-MS spectra (respectively) here in 2011. Big grin

I just recently posted crystal pics, m.p. ranges, and LCMS spectra. Hexane/heptane recrystallizations allow everyone get >99%.

the real challenge has been psilocin salts.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
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Brennendes Wasser
#26 Posted : 1/25/2019 10:40:57 PM

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Yes I read the LC/GS-MS Data already before I created this Account, but the meaning was that there are no NMR Spectra and the post implied that the first here on the nexus seemed to not grant any interesting insights, which sounds strange to me.

There is a reason NMR is the #1 analytic method in organic chemistry since ages and also in the future, IMO upon the choice of a standalone analytic method it yields the most structural information about a chemical compound available.

If we take a look at Chapter "4.) non-recrystallized impure Spice" the MS could retrieve some molar masses of the possible contaminants. But based on the NMR it was even possible to state that there are only hydrocarbon signals and no aromatic moietys / esters / carbonyles contained in all of the impurities or at least not in a detectable amount.

Also it was possible to track the formation of N-Oxide at Chapter "5.) Photooxidized Spice" with LC-MS and see the new peak forming, but with NMR it could be shown that the N-Oxidation is the only relevant reaction upon UV-exposure and the comparison of N-Oxide Signals to native Signals allowed to directly tell the ratio of oxidation. I guess therefore this experiment was t he first one here on the nexus or elsewhere to give actually exact numbers upon the process of UV-decomposition, besides giving an insight to the initial reaction.

Therefore I think those results are pretty unique and NMR is a powerfull tool, therefore I am very excited towards samples that contain only the impurities, as so far I only got molar masses with MS.


Of course the quote that people here also get 99 % + purity spice by recristalling is true, but every Chapter has a special question to be answered by that measurement and the question was:

"How pure can Spice be when derived directly out of the extraction path?"

And I think the outcome is truly interesting, as normally nobody would say you could leave out the Re-X as you would get 99%+ purity directly out of your freezing glass. Even if there may have someone been who know this for whatever reason, this is the first NMR to prove it, so why not post it here?

Sounds as if I want to defend what I posted here and why I did it - but that is simply data that I aquired. And therefore I post them here of course.
Even if all this stuff would be exactly like this on the nexus or elsewhere on the Internet - why should I still not post it here?

If there are people which get bored reading this stuff or already read it on Wikipedia, then I'm sure they wont follow this thread in the future anyways.


EDIT: Now I also uploaded the DEPT of the *Pure Spice* at #7. Well the DEPT is rather boring for this sample as it is already pure, but I measured it and forgot to upload. Maybe it will be interesting when measuring again something unidentified.
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
benzyme
#27 Posted : 1/26/2019 12:19:41 AM

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Thumbs up

welp, the more data, the better.

was good to see more MS spectra that matched what I got, for a synthetic sample.
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Mindlusion
#28 Posted : 1/26/2019 1:03:44 AM

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Brennendes Wasser wrote:

And I think the outcome is truly interesting, as normally nobody would say you could leave out the Re-X as you would get 99%+ purity directly out of your freezing glass. Even if there may have someone been who know this for whatever reason, this is the first NMR to prove it, so why not post it here?


This has been known, people usually only do the re-x to get big and pretty crystals.

I feel you. Mass spec is certainly powerful. Especially those $1M orbitrap machines, if you get a chance to play with those the power is simply awesome. NMR doesn't even compare to what those are capable of. Though, what protein biochemists can interpret structure using NOESY experiments, that is also beyond me. Insane. Each serves its own purpose and both are invaluable.

Myself, as an organic chemist, im an NMR junkie. I run 100s of them for every mass spec I run, but having even GC-MS data ontop of NMR when determining unknowns is usually necessary. As well to determine minute impurities <1%. I've posted some spectra too of different molecules but they usually remain temporarily.
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"The most beautiful thing we can experience, is the mysterious. The source of all true art and science."
 
GLTASN
#29 Posted : 4/20/2019 10:04:11 PM

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Are the images still avail. for this thread?
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Brennendes Wasser
#30 Posted : 4/20/2019 10:37:22 PM

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Crap why did they get deleted ...

Yes I can reupload them in no seconds.

But maybe it would be cool if I host them somewhere where they will never get deleted. But I actually thought that at this page they would never be??

I will upload them at the Nexus and refer to them with the [img ][/img ] function.

Will see if I do it now or the next days, but if you need the pictures RIGHT NOW then just download them at the end of each post. There you get them in the .ZIP file and they are named so you can find the connection to the text. Thumbs up
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
SnozzleBerry
#31 Posted : 4/23/2019 4:46:26 PM

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Brennendes Wasser wrote:
But maybe it would be cool if I host them somewhere where they will never get deleted. But I actually thought that at this page they would never be??

I will upload them at the Nexus and refer to them with the [img ][/img ] function.


If you do them as attachments rather than hosted on an external site (or host them via nexus and then link, as you suggested) you should be good. It appears the issue was with your external hosting site.

Nexus is now. Nexus is forever Laughing Razz Love

Thanks for the work here Smile
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Brennendes Wasser
#32 Posted : 4/23/2019 9:38:31 PM

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Yes sure - but for these Posts it is 100 % needed that all those pictures are EMBEDDED and not attached to the END of the post : /

But with a regular Upload you cannot make the first option.

Thats what I said in the last post - but I also said I may just upload it as a regular attachment to another thread and then use those to make the EMBEDDED pictures here in this one again.

I guess tomorrow I will do it, I will just use this Thread as a junk bin for all of this and possible next stuff. So dont wonder if you come along that linked thread, it can be ignored. But I dont know any other ways to do it than creating somehow 2 threads.

So if any of you also wants to embedd pictures somewhere, then you also could use that Thread as a Junk Thread for this ;D

So you will see pictures back up within the next days ...



More on topic:

Sadly I fear that not much will be continued in this thread, as it looks like my university career is going another route.

Originally I was very convinced that I would finish as an Organic Chemist and therefore have access to the nice analysis methods in this area for years on.

But now I actually decided to go another route and therefore I dont have access to NMR myself anymore - or let's better say I dont have the credentials for this, so it's nearly the same as not having access to this at all.

Therefore if this is not changing, I would have to rely on others to append samples and I dont think this is happening anywhere near. But I have to keep my fingers crossed, who knows how it's going to work out!


That makes me sad as I had some new good ideas:


- Deplete a MHRB cook with DMT and then extract the depleted soup with Touluene. That would pull only the so called *Jungle* and may give a better insight on what it may or may not be than the stuff I did, measuring *Jungle Spice* and then subtracting the Signals of Spice itself.


- Do some Analysis on the *Fats* that are in the root bark, more in Acacia then - of course it's uninteresting waste, but would be nice to at least try to get some more info about it.


- When the basic soup is heavily salted, then something precipitates and forms a black porous solid mass. Would be cool to check what this is actually. But I did not get this into solution, neither Water, nor Ethanol, nor Acetone, nor Limonene, nor Naphtha and I also think not in DCM.


Not actually DMT, but also possibly intersting:


- Do some measurements on the Stuff that you get from seeds of Anadenanthera Colubrina that still has its fearsome vomit-toxins and the junk left over after recrystallization. Would be very interesting what these *toxins* are, our nice Member 69Ron thought about N-Oxides of Bufotenine, NMT, Serotonine and therefore it would be hyper to get an actual insight.


- Do an 1H-NMR on the Harmala product from the regular TEKs without separation of both and then check their actual ratio. Also it would be interesting how much other stuff in inside of them if you do not do ANY precipitation by salting.


This is what is just in my mind now, maybe there is the possibility to still look at some of this stuff in the future.

Also I maaaaay have the credentials to use GC-MS, so maybe there will at least be a little more testing!
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
SnozzleBerry
#33 Posted : 4/24/2019 4:37:10 AM

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You should be able to upload and host on the wiki. I've done that in the past. I just went to check the exact process and the wiki is down. We're having some site issues at the moment. I just reset the forum and will try to get you the process for uploading/hosting via the Nexus wiki. Cleaner than a throwaway picture thread (at least, in theory Pleased )
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SnozzleBerry
#34 Posted : 4/24/2019 5:00:51 PM

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Ok. So go to the wiki homepage and login (or create an account if you haven't already).

Then you should see this on the lefthand side of the page:

Upload, use that link, and voila. No need for a junk photo thread Wink

Hope that helps Smile
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Brennendes Wasser
#35 Posted : 4/25/2019 12:11:06 AM

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Ok all pictures back online now again.

I also reuploaded the prediction of Yuremamine at the first page.

And that day I said *Ah well I dont see how Yuremamine could be hidden inside "3.) 1H+13C NMR Spectra of what was once called *Jungle Spice*",
but now I actually watched twice on it and I maaaay got an interesting insight on this.

In the following there is a slice of the predicted spectra and the one from 3.). And I think the Signals between the aliphatic and the aromatic range (4 - 5,5 ppm) somehow look similar. They have the same multiplicity and roughly the same shift. Also there are no other signals within that range, so IF Yuremamine would be hidden in this spectrum, these signals could indeed be those. Even the integral is correct: it's a 1:3 based on the one with further shift. Hmmm suspicious.

Here is the picture of the comparison:





Ok but how about other signals that would then also be in the spectrum of 3.)? (referring now to the numbers given by Mestrenova 12.0 at the predicted spectrum at page 1 and in the picture above)


Where is the big Dimethyl-Signal 23 + 24?

-> it could be the one at 2,08 ppm - The shape of this signals even looks very much like a strong methyl signal


Where are the aliphatic signals 9, 10, 20, 21 in the 2,6 - 3,3 ppm range?

-> they could be hidden below all those other big peaks in that range. They would just be minor artefacts - not that safe, but it could be. As the prediction is not 100 % accurate, they may indeed be hidden, even though the prediction may place some peaks outside of the measured ones.


Where are the aromatic signals 27, 31, 2, 6, 3, 17, 18, 19, 16 in the 6,5 - 8 ppm range?

--> they are definetly hidden below all those other aromatic peaks in that range. As the prediction is not 100 % accurate, they may indeed be hidden, even though the prediction may place some peaks outside of the measured ones.


Where are the phenolic protons 32, 33, 34 ?

--> they would not appear, as they are even more prone to D-H-exchange than regular alcohols. Therefore we observe proton 25 as it is not a phenolic alcohol, but not the ones above. Ok but then it is strange that phenolic proton 35 still would have been measured ... this is a contradiction to the stuff just told.


Ok so now there are only the signals at ~ 4,5 - 5,25 ppm left that should be visible definetly if Yuremamine is hidden in this spectrum - and there are some signals like those indeed in 3.).


And now why are there none of those in the 13C-NMR Spectrum?

C-NMR is way less sensitive so it may not catch up all the minor components, therefore it would not be too surprising if we dont observe any signals of Yuremamine there. Nevertheless there are a lot more aromatic signals and also (obviously) at different chemical shifts, so these still could be the Signals from that other aromatic rings in trace amounts.



Not sure if this is a tiny proof, but at least I would not totally exclude the presence of Yuremamine in 3.) anymore. Sadly I did not do a MS of that sample that days.

So Yuremamine was originally extracted using a cold methanol soak and was thought to be destroyed upon heat. It's a big molecule so that is very likely, but has there actually been a proof of this? I think nobody ever outside "serious research" had pure Yuremamine and tested what happened in aqueous solutions at 70 °C +.

Just a brief addition:
I looked for the XLogP3, which gives an idea about the polarity and therefore the solubility. DMT is at 2,5 and Yuremamine at 3,1, which would indicate that Yuremamine should be less polar than DMT. That is strange, because it seems with Naphtha Yuremamine is not extracted, only with stronger solvents like Toluene or Methanol.


downwardsfromzero wrote:
It is very likely worth taking a look at the predicted spectra for 2-methyltetrahydro-β-carboline (IMO)...


I completely forgot about what you wrote that time ago, maybe gonna add this soon and look for signs if the Tryptoline is in there. I read it's possible that under high heat tryptamines may form their tryptoline forms. But I forgot the name of that reaction ;o
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
endlessness
#36 Posted : 4/25/2019 10:44:31 AM

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Yuremamine won't be there because it breaks down with the extraction conditions like pH changes.

Did you look at the other jungle spice/dmt analysis threads to see what we have found to be in so-called jungle spice?
 
Brennendes Wasser
#37 Posted : 4/25/2019 10:55:47 AM

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Yes so during that time I wrote it cannot be in there, because the conditions will destroy it - but I thought that this was always quoted, but never tried with pure Yuremamine - at least not reported if so. Therefore I had this new idea Confused

Other compounds according to burnt's Thread and your Thread there is:

NMT
1-Methyl-Tryptoline
1,2-Dimethyl-Tryptoline
2-Methyl-Tryptoline

and trace amoutns of:
Hordenine, N-Methyl-Phenetylamine, Dimethyl-Phenetylamine, N-Formyl-NMT

Maybe I may have a look on that, I already had a prediction of 2-Methyl-Hordenine to look on for today.
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
XJ9
#38 Posted : 12/20/2019 10:44:30 PM

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What an amazing thread Thumbs up
Please contact me if you have experience working with Acacia Longifolia or Maidenii Smile
 
burnt
#39 Posted : 5/15/2020 6:07:41 AM

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Great thread. Love the NMR data and explanations.(NMR is like a god is to a prophet compared to mass spec, just kidding i love both techniques although if I had to choose I'd worship the magnet god).

Tip: if you want to use NMR to determine purity I'd suggest mixing with an internal standard. You can then use the intensity of signals from your standard of known purity to quantify signals from your analyte. There are some adjustments to parameters you typically make (I forget off hand what they are and it does depend a bit on a number of things I also don't remember) but its easy and straight forward way to get more accurate % purity on a weight basis.

 
Brennendes Wasser
#40 Posted : 5/15/2020 11:01:51 AM

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Well originally I was hoping to deliver much more stuff, but since 1-2 years I dont have credentials to NMR anymore and not sure if I get them at my new position. Therefore I can only engage another person to do it and I dont want to overengage her ... Confused

Right now I'm waiting for a measurement regarding 5-OH-DMT, but then I may finally pass over a sample with the "pure Jungle". Maybe this is then the last sample for the next time Crying or very sad but at least I would get this finally done, as the Signals may hint if there is even any common structure of a possible psychoactive compound or if its just a mess of "oils" and terpenes, which are not likely to be psychoactive at all.

Regarding purity determination that would be cool, but as long as I dont do the samples on my own I want to keep them on a minimum. Sad
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
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