Welcome to my Thread of DMT Analysis

In the following I have some interesting stuff with you to share. I did not implement this into that other plant-analysis thread, because I want to make a bigger concentrated post here and I also want to expand it over the time. Now this thread is quite crowded with a lot of data and pictures. If you just search for more focussed short information about DMT and it's analogues then I would recommend to check this other thread.




I did multiple different analysis on DMT for different intentions and conclusions. Here you see I made 1 new post for 1 new analysis, so it is easier to read and keep the overview.
If the extraction process for the samples or the analytical setup or machines are of interest, I may answer to this later, to save space I won’t write too much about that here. Last Info: NMR was done for all samples, but HPLC / LC-MS was only done for a few. May come back with more later.

NMR Info: 300 MHz in CDCl3-Solvent,
HPLC + LC Info: Reverse Phase C18 with Water / Acetonitrile Gradient,
MS Ionization Method: ESI

In case the Pictures are offline, you can still download them from a .ZIP file after each post. So that stuff won’t be lost even if I vanish here = )
Also if it's hard to see anything: Right click -> View Image or just download the .ZIP package.

The content so far is:

1.) The predicted 1H/13C NMR Spectra of DMT (done with Mestrenova 12.0)

This will be the base for my samples to be compared to and check what’s going on there. Of course the prediction is not a tool to be totally free of mistakes, but I was never disappointed by this function at all at any time, also for this work. (Predicted with Mestrenova 12.0)

2.) 1H+13C NMR Spectra of yellowish-white DMT

This DMT is not perfectly pure, but what you get when you have white crystals with some yellow to brown colour. I wanted to use this example to show, that even this visibly orange impure stuff is already very good in terms of purity for usage as you will see.

3.) 1H+13C NMR Spectra of Jungle Spice (I posted it in the original Plant Analysis thread).

I will incluce some little thoughts of what I think about the idea of *Jungle Spice*

4.) 1H+13C NMR Spectra + Mass Analysis of non-recrystallized DMT = with lots of impurities

I wanted to use this example to show what you get, when you have this brown crude oily stuff and what you can expect in terms of DMT-content when using this. Of course non-pure can be non-pure in any means, so I can just share what MY impure Sample is and only what I got at that specific moment. Still possibly interesting. I also tried to subtract the Spectra of the more pure DMT from this one to show only the Peaks of the contaminants. Sadly I dont have much to tell about them, but a future plan is to add a spectra of ONLY the contaminants, which are washed away by recrystallizing. This will be intersting for sure : ).

5.) 1H+13C NMR Spectra + Mass Analysis of photooxidized DMT

Here I wanted to investigate WHAT is happening if you don’t store your DMT correctly. We all know it breaks down, but here I unveiled in what dimension it will be destroyed and what is formed. At the end I can now finally tell how much DMT is destroyed within that exposure time given. Also I may post a longterm expure within the future.

6.) 1H+13C NMR Spectra of DMT which is exposed to high Heat (100 °C only so far).

Here I wanted to check, if DMT is truly sensitive to Temperature only, or if Temperature alone is not a problem at all when UV-Light is not combined.

New additions:

7.) 1H-NMR + 13C-NMR + DEPT of DMT with maximized purity directly out the extraction pot

-> This shall check to what extent impurities remain in Spice when you do NOT want to make further steps to purify it and just use what you get after freeze precipitation. Only 1 variation was done to the regular process: Naphtha with Hexane + Pentane was used instead of Hexane + Heptane. This gives a purer product than the *regular* Naphtha.


8.) 1H-NMR of crude Harmalas (scroll down a little bit from there)

-> This shall just check the ratio of Harmine:Harmaline and if Vasicin is present in the mixture. No Manske was done while extracting.

Future plans so far:

- 1H-NMR + 13C-NMR + LC-MS of the reddish / dark IMPURITY only, which is present when extracting -> this may unveil what exactly is pulled with our Spice, which we toss when recrystallizing

- 1H-NMR + 13C-NMR of boiled DMT Salt -> Cooking DMT*HCl for like 10 Hours at 100 °C and checking if it degrades (interesting for some TEKs to know how heat resistant it is in solution)

- 1H-NMR + 13C-NMR of long-term photooxidized DMT -> Checking how further exposure of Light to a sample will damage it, or if there is any moment where the degradation stops (due to any reason)

- 1H-NMR + 13C-NMR of DMT exposed to Air with a fan for a long time with exclusion of direct UV-Light and heat -> that shall check if DMT really degrades if it is cold and dark, but a lot of oxygen coming in contact with it.

(done with the Software Mestrenova 12.0)

So here is what Mestrenova 12.0 tells you which Signals N,N-Dimethyltryptamine will produce if you investigate it via 1H + 13C Nuclear Magnetic Resonance Spectroscopy.
I have numbered the Atoms and assigned them to the spectra.

IMPORTANT: H-Atoms are left out for easier view, but I have labeled their linked atom instead.



The proton Signal at 10.1 is very likely to appear with a different shift in a real spectra or not visible at all. This is often the case with protons at that position – they can be exchanged with other protons and in this case with Deuterium, so that you cannot track it in NMR.




These NMRs will be the base to be compared to what I have to show for you. Based on that one may discuss what alterations are undergone to the samples that will be discussed later on.

Spice extracted with Naphtha, NO defat, Colour is orange-yellow-whiteish. This shall symbolize what one would actually call *already very good usable, but still definetly not pure spice*.
Therefore I would like to use this to discuss how usable spice at that stage really is. But of course keep in mind: this discussion can only be refered directly to that one sample here which I got. Picture:



Here is the 1H-NMR of that sample. The molecule is included in that picture to show what Signal belongs to what Atom.
But in all future NMRs this will not be shown anymore, just come back here to check it:





All the Signals are very nicely visible! But actually it was totally clear that the signals should be visible perfectly, otherwise I would have had a sample of something different than spice =P. So let’s move to the other signals:
There are only a few which don’t belong to DMT: 5 Signals and the Signals that only have an Integral of 0,81. Compared to the Integral of 15 from DMT this is only a very low amount of unfamiliar Peaks. When calculating, the DMT-only-Signals are 94,62 %, which is surprisingly high as it still has a slightly yellowish / orange colour!


Here is the 13C-NMR of that sample. The molecule is included in that picture to show what Signal belongs to what Atom. But in all future NMRs this will not be shown anymore, just come back here to check it:





Well not much to say here. The Spectrum looks perfect. ONLY the DMT Signals visible – hooray! Don’t be confused by that thing at ~ 77 ppm. Dichloromethane (DCM) always produces a Signal at 13C-NMR as it also contains a Carbon. For the other samples the 13C-NMR will also not be of that interest ... it’s mostly included to give a complete view of NMR, but for 5.) Photooxidized DMT it will also be very interesting.



As told in the Observation in the 1H-NMR, the total Signal Integral of DMT is 94,62 %. Therefore it is already a condition of superior purity. Even if we may see really strong colours except white, being it orange or yellow, the DMT may still be more than 90 % + pure. But this is of course still only refering to my sample. But you could probably compare your sample to the foto of mine and judge by view, if the purity level could be around the same based on the colour comparison.

At last it would be interesting what the impurities are. But as they are only visible in trace amounts it is impossible to check them for any multiplicity etc. This is also a reason why I will post a Sample of the IMPURITY ONLY within the future. Then we may see the signals isolated and nicely.
But what can we says based on this: The only foreign signals we observe are in the range of 0,77 – 2,30. Those are aliphatic signals, meaning that they are produced by C-H bonds in saturated molecules. This would fit to molecules like Naphtha (but this should definetly be evaporated to a point where it’s invisible) or plant fats.
Maybe someone will have a further thought on this, but I think we may get some more information when I have that Impurity-only-Sample ready.

Spice pulled out of MHRB, NO defat, NO Recrystallization, Solvent: Toluene (not heated)
aka. this is what people believe to be the *full spectrum alkaloids jungle spice*. It is a viscous orange-brownish oil.



Here is the 1H-NMR of that sample.





So in this picture we see the same Signals for DMT as in "2.) yellowish-white DMT". This means that – surprise – this sample is also very high in DMT. But now the big question would be: As we got *FULL SPECTRUM* now, how much of that Full Spectrum is DMT and how much is other stuff?

Well now ... I am very sorry to tell you (for at least this sample):

This *Full Spectrum* is *Full DMT* or at least it it so much DMT that I hardly believe, that even if that other signals belong to any component which COULD be psycho-active, it should not be noticed upon ingestion.

Signals of DMT = 81,25 %. Now one may say: Ok, but there is a lot which is not DMT itself. Yes, but as you will see in the following section "4.) impure Spice" this is likely to be mostly the same brown junk that contaminates uncrystallized Spice.

If we subtract the Signals that are definetly just Junk also present in that other Samples, then we have only 7,5 % of Signals which COULD be new. And even this is highly debatable as this sample is the most unpure of mine here, so even this may just be Junk which was not visible in any other samples, as it was not contained enough to show up.
So even if ALL other signals would only belong to 1 other compound and this would be also a psychoactive one, then 50 mg of that Jungle Spice would be 37,5 mg + of DMT and only 4 mg of that other Alkaloid at maximum (!). And those other signals labeled with X definetly don’t make up a Tryptamine-like compound when counting them together.
Now one may think: Well but if other Tryptamines are *hiding* within that DMT Signals, couldn’t this also be the case?

Well if then, it can be said that nearly all possible Tryptamines are N,N-Dimethyl-Tryptamines (no other Signals of Diethyl-, etc.) and the Ratio of the 2x CH2-Groups to the N,N-Dimethyl-Groups is nearly a perfect 2:2:6.
Then it could be that there are Tryptamines with a Substituted Ring (like MeO, AcO, ...). If then, that Substituent should have a shift on the aromatic signals at 6,91 – 7,55 ppm. But we do not see any trace aromatic signals, shifted to higher ppm scales (like it would be for MeO- etc.). Therefore (at least in a relevant amount) there is no other Tryptamine visible.

Here is the 13C-NMR of that sample:





Not much to say here again. All big Signals are made by DMT, other signals are only visible in trace amounts. Again: if we would have another Tryptamine contained, then we would have for some Signals a only slightly shifted second Signal directly beneath. But when looking at the Signals, there is no tiny double Signal visible. Therefore I also think based on the 13C-NMR one can say that there is no other Tryptamine included in that Sample – at least at a relevant amount (!).



As discussed above, the Sample contains nearly only DMT and the same Junk as other impure Samples. This is strange, because it is actually a brownish oil (!) and nowhere near a white crystal. But I have had multiple moments where only trace amounts of impurities make that whole sample getting oily and dark.

As I discussed it is nearly impossible that there is any other Tryptamine in a relevant amount contained. Now there are only that other signals left to contain a possible other psycho-active compound, but in this case again: the content of that other componend is way too low with 7 % and we even have to consider that it is not only 1 different contaminant, but a cocktail of other compounds.

Therefore MY CONCLUSION is that *Jungle Spice* is only DMT with all that reddish-brownish oils which we got when pulling with very hot Naphtha (very comparable to 4.) impure, crude DMT). You shall use Toluene for this and NOT recrystallize ... wow surprise! You just get DMT + mostly Junk So everything which is included there is only that brown crap which we otherwise try to get rid of when doing a recrystallization. In my eyes: *Jungle Spice* is only a myth and for me (at least) now tossed into the bin (at least judged by this sample).

(also see here)

= with lots of impurities



Spice extracted with Naphtha, NO defat, NO Recrystallization, Naphtha heated to its boiling point when pulled (60 °C), so you would already expect it to pull a lot of junk. Colour is orange-brownish and the sample is an oil. This shall symbolize what one would actually call *crude, impure Pull*. Therefore I would like to use this to discuss how usable spice at that stage really is. But of course keep in mind: this discussion can only be refered directly to that one sample here.



Here is the 1H-NMR of that sample:





Again: this is mostly DMT. This is really strange ... actually I was definetly expecting it to be FULL of other Signals and the DMT Signals would only be a smaller part. This time the 2x CH2-Groups don’t have a nice 2:2 Integral, this indicates that there are may be some other Signals hiding below that 2,85 – 2,91 Peak. If we would assume that the DMT-Signals itself should have an Integral of 15 and we subtract everything we see beyond this 15, then we have an Integral of any other stuff of 3,59.
So this means that the DMT-Signals make up 81,50 % of that Sample. Well and regarding that when judging by Eye, this Sample looks pretty contaminated, this is a remarkably high amount of DMT in it!

Here is the 13C-NMR of that sample:





Well also the 13C-NMR shows mostly DMT Signals. We only see other Signals at 25,58 / 36,29 / 52,4. And all those Signals are again within the aliphatic range. Within the aromatic Range at 110 + I would not say that there are any new Signals.
Here is a comparison of this sample to the more purer one from "2.) Yellowish-white DMT":



You can see that there is in fact not much of a Change. Yes the lower one has more foreign Signals. But definetly NOT very much! Still mostly DMT.

Here is a Picture of only the DMT-Signals substracted from the 1H-NMR of that sample to show everything but the DMT itself:





Now those are the Signals of the most important Impurities, substracted from the original Spectrum. Trace Impurities, which are definetly irrelevant, are left out. Mestrenova already made a suggestion of what Integrals they could have, IF this would be 1 solely Compound (which it's not for sure).

Here is the HPLC Chromatogramme of that sample:





This is a Chromatogramme of that Sample using a gradient of 20 % to 60 % Water to Acetonitrile with 1 % Trifluoracetic acid.
Here we have a giant Peak which must be the DMT and nearly no other Peaks. Based on this we would state that this is extremely pure, but in this case I would say that we already know by the NMR that it’s not that pure, that impurities seem to be not visible at 220 nm (which should be the case if they mostly consist out of aliphatic hydrocarbons. Otherwise it may be that they don't move on the column. So sadly not much of an increase in knowledge by this.

Here is the LC-MS Chromatogramme + Mass Spectrum of that sample (DMT has M = 188,269 so it should be at 189 if it’s positively charged and at 187 if its negatively charged):





Well if one is familiar with that Stuff he/she may see that I packed way too much substance on that column . But it is hard to judge the correct amount just by eye and I did not want to run that many tests, so this is what we got.
What can we see? There is DMT (M = 188,269 g/mol) at 8 min and as it is too much, its still eluating until ~ 10 min. Afterwards there is 1 new Peak at 11,5 min and 1 in the beginning at 5,5 min.

Now: What is the Mass of that Substance(-mixture) at each peak ?

Instead of writing it here you can see it in the Picture. DMT is visible – hooray! But what the others could be, no idea so far. Possibly someone has a clue, I will leave this for open discussion now hahaha. The mass of 227 negatively charged could be a DMT-Acetonitrile associate. Those Solvent-Associates are common for ESI-MS. This will also occur in every other MS spectrum of DMT with that eluents.



Now as I showed this impure Spice Sample to you I want to add a comparison between the Spice from 2.), the very impure Spice from 4.) and the Jungle Spice from 3.). In my opinion this comparison shows that Jungle Spice should be mostly just regarded as very unpure Spice:





Interestingly judged by this NMR, the purity of that Sample is 81,50 %.
This is remarkable in my eyes and shows again: there is not that much of other components in the nexian' pulls hahaha .... But of course I’m very curious about them now, but based on that Spectrum I could only tell again that there are Signals of Oils and now possibly something with an aromatic / unsaturated molecular structure.

Therefore I have to say again it will be very interesting to test an Impurity-only-Sample. Then we will have a really good look on all that foreign Signals and we may finally get some more precise info on the Impurities and also whether they are all aliphatic or not etc.
The MS Spectrum gives some Masses of the other components, but if we don’t even have a slightest idea what the exact formula of those is, we won’t get too much information off this.
At least it’s to say that there is no Yuremamine (M = 476,53) visible, but that is not that astonishing, as it seems that you get it ONLY if you do all-cold extractions.

The same Spice as from 2.). This time it was laying in DIRECT SUN outside for 2 days.
Actually I have to add that it was some time partially covered with a standard kitchen plastic foil as I was afraid of rain. But I think we may still say it was exposed to ~ 2 days of direct sun.



Now before showing the NMRs I have a new NMR Prediction. This time: N,N-Dimethyltryptamine-N-Oxide. So I did not know what could possibly happen while this sample is standing in the sun, but a fairly senseful reaction would be just the addition of an Oxygen out of O2 from the air onto that lone electron pair of the Dimetyhl-N.
Therefore this is the calculated spectrum of the N-Oxide, this time calculated with Chemdraw Ultra instead of Mestrenova (doesn’t look so nice, but its smaller in size):



Where comes the difference in the NMR between the standard molecule and the N-Oxide? I can tell you afterwards if you want. Now let’s have a look if this is indeed forming ...

Here is the 1H-NMR of that sample:





Hell yes! Maybe it is not visible in the first sight, but watch your eyes, you can PERFECTLY see a smaller Set of

- The BIG Methyl Signal
- Both of the 2 CH2 Groups

with a shift to the left – as predicted. Well in this case the shift told by Mestrenova is not exactly what we see here, but that does not need to worry us, it’s just a prediction and this IS the N-Oxide.

And now what the REALLY interesting part is: There is NEARLY NO other stuff contained here, all other foreign signals were practially also visible in the unoxidized sample.

This means: Upon UV-exposure the N-Oxide Formation is the ONLY relevant reaction (or at least within 2 days).

Let’s do some calculations in the Conclusion section. Side info: it was wrong to normalize the aromatic Signals to 5 as they also contain that ones of the N-Oxide. I rather should have normalized the Dimethyl-Signals to 6. But that really doesn’t matter, as the important thing is the comparison of the DMT Signals to the N-Oxide Signals and for this its totally unimportant. =P

Here is the 13C-NMR of that sample:





Well to be shorter here: We get the exact same thing. We have the regular DMT Signals, but we also have the SHIFTED Signals. One is shifted slightly to the right instead of left, but that should be fine. Also no relevant other Signals, except DMT and the N-Oxide. Cool!

Here is the LC-MS of that sample, where we should be able to also observe the formation of the N-Oxide. DMT itself has a molecular weight of M = 188,269 u so as like we saw in 4.) its peak will be at 189 u in the MS. As the N-Oxide has an additional Oxygen, which weighs 16 u, we will have 189 + 16 =205 u IF we can observe any N-Oxide. So let’s have a look.





Wow! What a nice result. We got 2 very cool aspects here. The first: We perfectly see the DMT peak, which is by far the main peak in this complete spectrum. And directly beneath there is the Peak of the N-Oxide. If you take a look below: You can see in the spectrum of the positive charged Ions we see 189 for DMT and that other Peak has 205.
Side info: Even though DMT is less polar than the charged N-Oxide, it is eluted faster. The reason: In the eluent is also Trifluoro-acetic acid, which creates DMT*H+ and this compound is more polar overall than DMT+O-. This is the reason why the N-Oxide seems less polar than the unpolar Freebase.

Well let’s do some hardcore math: 205 – 189 = 16 !
Hooray, that other Peak is produced by a Substance which is DMT + 1 Oxygen ... N-Oxide!

And so we can say also based on this LC-MS:

Upon the exposure of UV-Light to DMT we NEARLY ONLY observe the formation of N-Oxide. No other reaction or any new products in a relevant amount are observed. (I know there are other peaks, but they are quite small and are possibly just the signal noise ...)



Ok what can we say now? Based on the NMR + the MS we can identify the formation of the DMT-N-Oxide and nearly no other relevant products. Therefore I may conclude: Upon exposure of 2 days of direct sun DMT partially gets converted into the N-Oxide and not quite much else.

But what is the cool part now?! We can even do a really nice math, which I guess has not been done before. Calculating, how much DMT gets destroyed/converted within that time.

For this we just divide the Integral of the DMT-Signals with the Integral of the N-Oxide Signals. For this we should only use the Dimethyl-/CH2-Signals.
Here we get (1,05 / 8,96) * 100 = 11,72 %.

So now I can finally say: Upon UV Exposure of 2 days, 11,72 % of the DMT will be converted into the N-Oxide. = D

I’m doing a longterm investigation sooner to check if this is a continuating process or if it stopps after some time.

UPDATE: Check what happens if you heat for 10 days to 70 °C and also add a Base or Radical Initiator HERE. You will create DMT-Polymers.

The same Spice as from 2.). This time the plain crystals were cooked in the oven for 2,5 h at 100 °C.
With that sample I wanted to investigate if PLAIN HEAT directly damages the molecule. So here we have no UV light and therefore practically no O-Radicals.

Therefore it was interesting what high temperatures alone do. DMT was heated for 2,5 h at 100 °C and then NMR analysis was performed.



As for the colour normally Amines get brown by oxidation when exposed to air long-term, so this was my first idea. Maybe also just some pi-stacking and therefore causing optical range absorption, which create that color. If the DMT melts it will form any kind of molecular interactions that were previously restricted by the crystal lattice, therefore liquid DMT is mostly brown, even if it is pure.

Here is the 1H-NMR of that sample (ah I forgot to label what is definetly not DMT in this spectrum. But on the other hand his spectrum has no interesting statement neither as you will see):





Well ... so there isn’t really something to observe. We just see the DMT-Signals and the only new thing may be 1 Signal inside the big Dimethyl-Peak, slightly at the left bottom of it. But otherwise: there is NO evidence of an N-Oxide and also no evidence of anything different. It seems like that sample is still nearly completely DMT only and very viable and not oxidized - which seems impossible due to that massive weight increase.

Here is the 13C-NMR of that sample:





In this case it’s just the same as with the 1H-NMR. We see the DMT Signals perfectly and nothing else. Based on this sample I would just assume this is perfect plain DMT. No Signal of any other compound. This seems so strange.




Well so sadly we do not have any real conclusions here, but we can still say the following:

Upon hot temperature exposure the DMT gets brownish, but it seems like the DMT is still totally fine and able to be used, chemically no degradation is visible within that spectras. The darker colour may come from pi-Stacking which is 2 or more DMT molecules interacting pretty closely with their aromatic (hence pi-electron-filled) Indol-body. Thereby associates are formed, which a loosely bound. That makes up a darker colour, as a bigger system of interacting pi-electrons is more likely to absorb light from the visible spectrum due to some quantum chemistry physics stuff (more interacting molecule orbitals create also lower energy electrons which can be excited with a lower energy amount that can be also reached by absorption of a visible-light photon. These have lower energies due to longer wavelength and therefore these transitions would not happen without the low energy electrons created by pi-stacking).


From here on all other future Results will be listed and added in the next post continually.

-New things are placed here continuously-

This time I wanted to unravel how pure Spice could get - directly derived from the Non-Polar-Solvent, meaning that there is not a single purification step after the Spice was obtained in its solid form.

The solvent used was a mixture of isomeres of Hexan + Pentan, meaning that this kind of Naphtha is the lowest boiling you could get (= 40 - 60 °C as opposed to 60 - 80 °C with Hexan + Heptane), which pulls the least other junk things besides the Spice. Then it was frozen-precipitated to give exactly what was measured here. Still overall solubility is much lower, therefore I dont recommend using it.





Here is the 1H-NMR of that sample:





Well to make it short: The spectrum is PERFECT. It contains - as always - all relevant DMT Signals - but it has NO other signals. Or at least those other signals are so tiny, you may really say that this even looks like the *Predicted Spectra* in Chapter 1.). This is really astonishing, as no workup method was used and this sample was derived directly from the freeze precipitation. Seems like in some cases it is not even possible to perform any workup, as the product is already practically 100 % DMT-only.

Here is the 13C-NMR of that sample:





Same case here: Again it shows only 100 % the signals of DMT - nice!


EDIT: So now here just for the completion as I finally have a let's say *Pure Sample* there is the "Distortionless Enhancement by Polarization Transfer" Spectrum -> *13C-DEPT NMR*

What is this? An additional key to unravel an unknown structure of a compound by telling what carbon atoms - based on their respective C-NMR Signals - carry how many protons or if they carry them at all. As we already know the structure of our sample of course, this is really irrelevant, but mostly just for the completion to present you a full set of NMR data of basically pure Spice.



Yes ... not that interesting, you just see what you expected. This DEPT method will be much more interesting when we have the impurity sample.




Well this seems that when you use the lowest-boiling Naphtha (40 - 60 °C, Hexane + Pentane) and PROPERLY wash the Non-Polar-Solvent in the end with a sodium (bi)carb-wash or something comparable and freeze-precipitate it afterwards you can already get practically 100 % pure Spice.

Normally in the science about plant ingredients and chemicals its a pain to get pure products or to verify a possible way to isolate them in a mostly pure form.

It seems that it is just a gift of heaven that Spice can be isolated that perfectly by that *easy* TEKs that are floating around here.

Based on this I would say that if your Spice is totally white and you did the regular steps until the freeze-precipitation, then there is totally no Re-X worthy - I even told in the upper Chapters that even yellow Spice seems pretty good - but in case you really want totally pure Spice, then it is definetly not worth to Re-X if it is already clear white.

Of course there COULD be some other components in your mixture that are also white, which were not present in this sample here. But I guess it should be highly unlikely that there may be any other compound that could cause any potantial relevant contamination, if it is not visible here even in a trace amount.





For the sake of complicity, here is the UV-Vis spectrum of DMT. Actually I have no idea, why anyone would need / use that, but I have it so here you go. If you look for more general chemical data on DMT and many other molecules, better just directly see here.

DMT in Acetonitrile, c = 7,5*E-4 mol/l



It's quite boring and no absorption in Vis-area, but hey, thats why we get white Crystals.


Also for complicity, here is the IR-spectrum of DMT. Same as above, but maybe it may prove useful somewhere in future. As it takes some time to analyse an IR-spectrum (at least if its not your personal hobby) there are no further details. Measured in attenuated total reflection mode.



What is also missing is an XRD of DMT - its an analysis on the crystalinity. That would be quite interesting, as it may get a deeper insight into the different DMT morphologies, that also have individual melting points. That may highly vary based on crystalinity, which an XRD can observe. I had the opportunity to use one in the past, but I did not have the balls. Maybe I may get an XRD of different morphology samples in the future.






This is just an 1H-NMR taken from a crude Harmala Alkaloid mixture. Harmalas were extracted with acid and simply precipitated with NaOH and washed until pH was neutral. No Manske precipitation was done, I have the feeling that it takes ages for these crystals to sink and filtering is not easy ...





Here is the 1H-NMR of that sample (in DMSO):





Not much to say here. Basically all the signals that can be definetly aligned to just 1 of either Harmin or Harmalin show a pretty good 1:1 of both compounds. Wikipedia says this:

Harmin: 0,44 %–1,84 %–4,3 %
Harmalin: 0,25 %–0,79 %–5,6 %
Vasicin (Peganin): 0,25 %
(Harmalol could be there, but will be hidden below other signals)

So also Wikipedia mostly says it's roughly the same, but in my case that sample really is pretty much a plain 1:1 with a difference of at highest 9 % more Harmalin (Methyl-Peak ~ 2,3/2,5 ppm). Now can there any other information be retrieved? Harmalol-only signals would all be hidden below what we currently see. But Vasicin could be identified: It shows up with Signals at:

4,5 ppm (s) (CH2 between aromat and N)
3,8 ppm (m) (CH at Hydroxyl-group)
3,4 ppm (m) (CH2 at alpha-position in Pyrrolidin-ring)
1,7 ppm (d,m) (CH2 at beta-position in Pyrrolidin-ring)

Now only 4,5 ppm will be not hidden in that spectrum and we can see no peak. So I would say quite confidently that there is absolutely no Vasicin in that sample. There was totally no workup step, so the Alkaloids were just crashed from the acidic boil. It is written that Manske-precipitation is needed to get rid of Vasicin. But actually it is also reported that there is no need for that, other than you would be pregnant. So I never made that hassle - but here obviously there is not even Vasicin present. So as it has a Hydroxyl-group, the solubility in water must be slightly higher than from the other 2 Alks. And as these samples were washed with excessive water, it must have been removed - a few g of Alkaloids were washed with 20 - 30 L of water.
So I may say: Just stop the Manske precipitation, which takes ages and may just make you loose product ... Instead put your freshly NaOH-precipitated Alkaloids from acidic boil in a 5 L plastic bottle and fill it with water, shake shortly and let it settle. This takes less than 5 min. Then decant and repeat. Do this until the water is clear and/or pH = 7 is reached.

This step will effectively combine:

1. Neutralization of any residual NaOH (so mandatory anyways)
2. (possibly) removal of any Vasicin. Takes no time compared to Manske precipitation!

Here is some information from _Trip_ about using Ethyl Acetate as an extraction solvent, which will also not carry over Vasicin when doing a citrate precipitation later on:

Excellent work, thanks for sharing!

Confirms what we have been researching so far regarding jungle spice being pretty much mostly DMT despite people still insisting on thinking it is very different..

I really like your experiments regarding oxidation too, thanks for that too

I've tested both yellow and white crystals, they both show up as dmt. The dark red viscous oil that doesn't dissolve in boiling hexane, shows up on my instrument as 581 m/z. It's definitely something more than a tryptamine, possibly some heterocycle of four rings, and other moieties. Yuremamine had been discussed as the probable primary component of said residue.

Yuremamine gets destroyed during typical extractions due to pH sensitivity iirc so it wouldn't come across

Your broad hnmr peak out at 8.2 is almost certainly the indole NH.
It's broad because it's an exchangeable proton.
There are several ways to prove this.
You could put a small drop of D2O in the nmr tube, shake, then re-run the sample. You should see almost complete disappearance of the signal.
Another method is to run the sample in CD3OD, rather than CDCl3. Again, it should almost totally disappear.
Another method is to run the sample at a higher temp, typically 10 degrees higher. This will sometimes sharpen the peak, or/and shift the peak.

Nice work.
I always had my money on dmt being less prone to oxidation, compared to what you have shown.

Yeh I think Yuremamine was said to be fully destroyed during regular extractions - its a giant molecule so there are surely many ways how it can break apart upon bad conditions.

And who ever would want to do a 4 weeks cold Methanol extraction, except if he definetly just wants to get the Yuremamine ? xD

Ok here is the predicted NMR of Yuremamine and I think especially the Signals at the highest PPMs aren't shown in any spectrum. Therefore I would say no Yuremamine here:

H NMR 8,5 +

C NMR 135 +

don't show up

(but actually also that other ones are missing)

1H-NMR:





13C-NMR:






And for the Indol-H:

Yes thats really a possibility, this would solve that puzzle, but I was very distracted by the Prediction of Chemdraw Ultra and Mestrenova 12, who both put them between 9 and 10.

But yeh ... those Protons are always not that precisely calculated to it may be possible and as I said this would raise the purity of the samples by far!


Another reason why I discarded to write this down is that other spectra of Tryptamines at Databases have measured that Signal also at way higher PPMs, just as Chemdraw Ultra / Mestrenova would have predicted ... see here:

The NH Signal (A) is the most left one at 11,11 PPM (SDBS database)



EDIT: YES leratiomyces is right! it is the indolic proton. I already corrected it in all the pictures now.

Prediction software will only give you a ball park figure for an exchangeable proton.
I wouldn't get caught up on the prediction.
Even changing the concentration of the sample in the nmr tube can shift an exchangeable proton a decent amount.
If you are nervous about your lump at 8.2, then run one of the experiments I suggested. But personally, I don't think you need to.

I will run another *Clean Spice* experiment in the future, but this time with the reall good re-x-ed one and if there is still that Signal with Integral ~ 1 it should be almost surely that indolic NH.

And of course prediction is vague in any case for those protons, but that from SDBS Database is no prediction, but really measured and I also checked more Tryptamine Compounds at the SDBS Database when I first saw my results and all those Signals were located higher.

But still it would be extremely plausible if this is the NH ;D

thank you so much for your work and for writing it in a way that i could follow

Great to see you've cracked the mystery of... embedded pictures

This is an excellent report, although in post #13 the structure used for the NMR predictions for yuremamine is missing the two methyl groups!

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


Keep up the good work!

Hi there, sorry - long time no post and therefore no new news.

Now I included the NMR-Spectra of Spice with the maximum purity what you may get directly out of the A/B-TEK with NO further purification step.

This means:

> Pulling with Naphtha made of Hexane + PENTANE (Boiling Point 40 - 60 °C instead of 60 - 80 °C)

> Washing the Naphtha with NaCl-enriched water

> Freeze-precipitating it



This yielded the sample that was investigated by NMR. Again all other signals and Spice-only Signals were used to calculate the percentage of purity, what could be received by the method listed above and with NO RE-X.



This means that with this method it is totally unneeded to re-x, even if you want 99 % + purity (given the prequisite that the product is of constant quality).

That was really unexpected I must say!


Also and maybe even more exciting: the perfect pure Spectrum also shows that *strange peak* at ~ 8.3 ppm and therefore it 100 %ly belongs to DMT itself, more precisely it is surely that NH-Proton labeled as #5 in the prediction as we were presuming.

This is nice to know, because then this signal is NOT an impurity anymore and all those other samples are of much higher purity. I already corrected all pictures and all the text regarding it.

Therefore it is nice to hear that even the most unpure sample here is 80 %+. You really would not have expected this by judgment with the eye x)




Soon I will bring you the *Impurity-only* Sample I hope. I'm quite interested in that, I guess Mass Spectrometry will be very interesting here again, as we dont have any structures in mind what it could be and it may help to get a rough idea.

Uh, where are you getting these numbers?

Since when is a 300MHz NMR capable of resolving peak ratios down to 5 decimal places? You know the resolution on the machine is much less than that right? Any impurities past <1%, especially on a 300MHz, are going to be in the baseline. You can't read more than 99% or >99% purity with an NMR, at least no one will take you seriously if attempt. You need to use LC-MS for that.

And on that note, even your integrations are only to 2 decimal places? so how is it even possible you getting digits past 1%? (0.01)

Any % purity or product ratios determined by NMR is ONLY reported to a single digit. 99% is as much as you can say or a clean spectra with no visible impurities you could report >99%.

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 .

Well this is from the Internet:



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