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Mimosa hostilis and extract analysis thread (FASA, FASW, Naphtha, Limo, "jungle spice" etc

Migrated topic.
Hmm, could the wildcard quantities of NMT and possible betacarbolines in "dirtier" STB extracts be partly responsible for the significant variations in trip experience?

To all those involved in these efforts; Thanks for all the work! I have been obsessively following this, the DMT N-oxide analysis, the entheogenic effects of NMT, and the Harmaline-to-THH threads. Great stuff.
Thats what I was mentioning before, personally I dont think that with the small amount of other alkaloids in mimosa, even using xylene or so to extract, are enough to feel the difference (except when taking oral cold brews with yuremamine...).

But there is very little good blind experiments to test this to give a definite answer.

It is known that some alkaloids that even by themselves dont have effects might change the effects of other active alkaloids (For example cbd/thc), but the ratios needed for these changes are closer together, not like the 1% or whatever small amount that the jungle spice or FASW/etc analysis have been showing of other alkaloids, compared to the overwhelming majority of DMT.

The thing also with psychedelic experiences is that they are by themselves so profound and constantly changing/dynamic, even from the same batch in very similar set and settting, that I always wonder how people can affirm with so much certainty that they feel the difference. I would think the set and setting and the expectations will make much more difference, and the natural oscilations/variety of experience will dilute any potential small differences these other alkaloids can make. Thats my hypothesis at least.

these other alkaloids could be concentrated on purpose in ways that have not been done so far, though, to attempt to bioassay these differences, such as in the water wash after FASI method mentioned in this thread (but care is necessary for bioassaying unknonwn compounds)

If one is talking about acacia/phalaris/etc extractions, thats a whole other story, depending on plant source.

nen888 said:
..lots to ponder! great..
Dozuki wrote:
NMT has now been shown to be in the extractions by GC-MS. I think this has some direct bearing on nen888's NMT thread
..actually, i was going to add a postscript to the summary of my lecture in that thread, which was to say that, due to the rapid darkening of NMT, i am open to the possibility that 2MeTHBC is contributing to the effects..the best chemical advice i can get is that the NMT is probably breaking down into this, or 1,2,3,4-tetrahydro-beta-carboline..it must be degrading to something to explain the color change, which was also observed by Shulgin...

nen, here's what inf was talking about regarding NMT and oxidation:

you should also check this page: http://www.anoniem.org/?http://chem...-chemistry/reactions-of-amines-oxidation.html

What it says basically is that tertiary amines (like dmt) can form n-oxides, as we know. Primary amines (i.e. the ones having -NH2, like mescaline) and secondary amines ( i.e. the ones having -NH-, like NMT) can also be N-oxidated, but the problem is that the oxidation reaction does not stop there but instead continues further on to create nitro compounds (i.e. ones having -NO2 group). So the reason for not referring to mescaline n-oxide or NMT N-oxide is that by the peroxide (or other oxidating agents like KMnO4) you get nitromescaline (mescaline-NO2) and nitro-NMT as the final products PLUS some intermediates, including mescaline N-oxide and nmt-N-oxide. All these oxidation products are, as I've been reading too cumbersome to isolate and analyze individually, hence the lack of references.
Also, let us not forget that 1,2,3,4-tetrahydro-beta-carboline is a cyclised product of NMT (or in other words an oxidation product, but obviously not an N-oxidation) just as 2MeTHBC is an cyclised product of dmt.

endlessness said:
Thats what I was mentioning before, personally I dont think that with the small amount of other alkaloids in mimosa, even using xylene or so to extract, are enough to feel the difference (except when taking oral cold brews with yuremamine...).
As for the activity, endlessness, one can however still argue that they can be so profoundly active that they change the trip qualitatively. It all has to do with their pharmacology, which, unless we have preparations of these compounds with a fair degree of purity for bioassaying we won't be able to assess...

Think of it this way; the dmt molecule is not a rigid molecule; the ethanamine arm has 2 bonds that naturally in solution rotate to give almost almost infinite combinations. Just check the diagram; bond α constantly rotates 360 degrees around itself and can be at any given place (anti-parallel compared to how dmt is clasically drawn to any position above or below the plane) at any given time. Same goes with bond β; it also rotates anywhere above or below the plane etc. These rotations happen all the time and in combination you can only imagine how many different conformations dmt assumes in solution...In contrast the indole part is far less restrained, rigid and not much rotation is allowed.

Now, think about this; when dmt hits its receptor (any receptor, it doesn't matter atm) there'll be a single or few conformations that will bind onto it. While dmt is bound to the receptor it'll also assume little rotation and conformational changes. Dmt molecules with the incorrect conformation while hitting the receptor will have to assume a more favourable one in order to bind properly and activate this receptor.

Now, what if 2MeTHBC, a molecule with much more conformational constrain and little fiddling around has just the right conformation for binding to the receptor in question? In layman's terms, this would mean that, e.g. if 1000 dmt molecules are hitting the receptor in question, only a small fraction of them will bind; but if 1000 2MeTHBC molecules (seen here as a locked in the ideal position for binding-version of dmt), then one can expect a 1000-fold higher activity of 2MeTHBC compared to dmt.

However, this can be seen the other way around; e.g. as a version of dmt that is totally unsuitable for receptor binding. It may seem far-fetched that 2MeTHBC conformation is the ideal dmt-binding conformation but given the amount of different receptors that dmt binds to and activates, it's very reasonable to think that 2MeTHBC will be performing better than dmt at binding even in one receptor, thus profoundly altering the experience.

Finally, to answer to Ice House, all this obscure crazy arcane chemistries are to try to further understand how stuff works and what it means for teh experience. Why? BECAUSE WE WANT TO TRIP MOAR AND HARDER!!!


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Excellent post infundibulum. So in terms of bioassay, one could try to isolate 2mthbc and bioassay small amounts of it with small amounts of dmt and see how it feels. Or get a standard to test it. I will see if I ever get the chance to.

What other way could we explore? Arent there softwares to predict activity with molecules?
benzyme said:
yea, i posted one three years ago... called tripos (benchware) muse.
benzyme, if you're more experienced with tripos, can you model how dmt and 2mthbc could bind to, say few receptors, like TAARs and 5-HT2 ones? Would be great if he at least had a prediction of how these compounds bind to in the active site!
..what was believed to be either 2MeTHBC or 1,2,3,4-tetrahydro-betacarboline, paper chromatographed from a couple of acacias 10 years back was vaporized (about 20-30mg) ..it had noticeable, though not visual or auditory, activity..
there were not the resources or time to formally identify the betacarboline..
..also, in another thread i can't find right now benzyme mentioned creating 2MeTHBC from tryptophan, and that it was 'active'..the Phalaris staggers theory that sheep are 'ayahuascaing themselves to death' via toxic dietary amines (see TIKHAL) leads to the possibility that 2MeTHBC is more potent than predicted in activity..

thanks Infundibulum for the great input..!
In the analysis of freebase DMT extracted whit naphtha there is no trace of naphtha component left.

I went through a analytical study of a concentrated cannabis extract thanks to naphta, the well-know "Rick Simpson Oil". In this study a residual solvent testing was performed, and naphtha was found (page 8) !

Cannabis Oil: chemical evaluation of an upcoming cannabis-based medicine

I wonder why residual naphtha component isn't found in the endlessness analysis.
Does the freeze-precipitation method reduce drastically the probability to get residual solvent component ?
A sticky-icky cannabis extract can trap a lot more solvent than DMT crystals. DMT goo is another story, but this can be heated to help release solvent. If you do that with cannabis extract you release all the tasty terpenes (according to that article).
Very interesting article by the way! Nice to see a comparison between different cannabis extraction solvents, and the effects of decarboxylating.
Hey there - I have something interesting to share with you.

I guess there has not been anything like this up here at all, so I just thought I may post it on the Nexus. There was a guy with the theoretical NMR-Shift of DMT and he posted it here:

No need for you to visit the thread as I will include the theoretical spectra also here, even predicted with the same programm and edited it so you will all understand what is going on here.

Just the short information at first:

You will see that what I extracted as *Jungle Spice* is nearly pure DMT. Therefore if you are going to create Changa (and no crystals) I would advise to go the way I did, as you will get still a nearly pure compound and the maximum yield.

Prodecure (just the key elements):

- 3x Hot acidic cook at 80°C for 1h each
- 5x Pulls with Toluene (evapped with vacuum)
=> slightly brownish (but very light coloured) oil, but not very liquid

Now for the Science Part:

I don't want to extend the thread so long, therefore you may check out the basics of NMR yourself. It is the main analysis for chemists to check whether they created the product they wanted and whether it contains impurities etc. NMR = Nuclear Magnetic Resonance (Spectroscopy) and in this process atoms will produce a special signal, depending on how they are connected to each other. End of short explanation ...

At first for the PROTONS, which means you see the 1H-NMR now.

(I'm still new to the nexus so I don't know how to properly attach files with the nexus' own attachement option)

1.) PREDICTED 1H-Spectrum:

You can see: I nummerized the atoms and marked them in the PREDICTED spectra. Normally we nummerize it from 1 to the last in the molecule and not in the spectra itself, but don't worry for this :p

RED means that this is very unlikely to be visible in the REAL spectra, as we would have to measure this for a long time to be visible etc.

1.) REAL 1H-Spectrum:

And now you see: ALL the signals are visible (except for the red one, but this is really nothing to care about). And what you also see: there are nearly no other signals, which indicate for a very pure component. The peak which is at 2,09 was labeled as a water impurity by the analysis software, but I am not so sure about that. Still nothing really to worry in terms of purity.

2.) PREDICTED 13C-Spektrum:

Ok so now we have much more Signals, as we also have more Atoms which produce them = C is measured instead of H. This time all of the signals should also show up in the REAL spektrum.

2.) REAL 13C-Spektrum

So this really made me wonder. Normally even if the 1H-Spektrum is very good then the 13C is containing some new peaks, which were not predicted. But for this time we also have nearly only our predicted Signals. And also at the correct place. Isn't this a wonder?


So I may say that in the terms of an synthetic work in the organic chemistry this compound would be labeled as *nearly pure* and be able to readily be used in a further reaction. When doing some laboratory stuff then you often get some Spectra which look much worse and you still think: "Ah **** it I will use that stuff anyways". So for myself I will now continue to NEVER defat, as I never intend to have a crystaline compound, as I will do Changa with this oily stuff and it does not matter then.
ALSO for the people who say: "Toluene will pull more Junk"

I cannot really see any quantitative sign of other molecules which would indicate a rough mixture instead of a merely pure compound. Therefore if you have the ability to fully evaporate the Toluene, I would definetly recommend to use that!

Hopefully it will be useful or can be linked if people are unsure about using toluene / defat or simply are interested in some DMT-Science. Hopefully also the pictures will work, as I am a newb to this site and used *pic-upload.de* for this : S (does it mean that the pictures will be deleted after some time and make this post senseless?)
May you please provide a detailed write-up as to how compounds were prepared for analysis, which field strengths of the magnet did you run the analysis at (in term of megahertz and Tesla)? Which models of spectrometers did you use, which programs did you used to generate these details? Which solvents did you use to dissolve them before analysis, and do you have certifricates of purity and account for the effect of potential water contamination? What temperature did you run your NMR analyses at? Please elaborate on your methods of preparation and analysis and let us know, then we may be able to give you an answer.

How was it purified? Given there were hot acid boils followed by NaOH bombardment then pulling into toluene without any mention of re-crystallization and other purification methodologies before analysis; if you didn't purify it well, your experimental readout will be inconsistent with other entries in the literature on it. What I would suggest is that you further purify you extract (HPLC is your friend) and then re-run it, as I am almost sure that your extract is riddled with contaminants. Pure, even relatively pure, DMT is a white to off-white crystalline solid at Room Temperature, standard Atmospheric conditions for planet Earth, and pressure of ~1 atm (760 mmHg). The "slightly brownish (but very light coloured) oil, but not very liquid" doesn't sound anywhere close to pure enough to generate a spectra anywhere close to reliable.

Well what do you mean with answer - so far there is no question o_O

I just want to post it here as I was curious about my Spice and did this NMR Measurement and I think there has nothing been like this before on the forums (and I think not many will have the opportunity to do it themselves).

Preparation is just as regular:

> 20 mg Substance (my oily stuff from the Toluene pull after evapped with a "rotationary evaporator" - don't know the real english name) + 0,6 ml CDCl3 (Chloroform as Solvent).

> NMR is measured at 300 MHz. Measure time was like 3 min, I don't remember, would have to look it up but I don't think its needed.

> Spectrometer = 300 MHz Avance III NMR Spektrometer (Bruker BioSpin GmbH)

> Prediction Software = Chemdraw Ultra 12 (CambridgeSoft)

> Analysis Software = Mestrenova 12 x64

> plant matter = Mimosa Hostilis Jurema

What do you mean with account for the effect of potential water contamination?

The Software Mestrenova itself can do an automatic detection of peaks and this function told this peak would be water. As the chemical shift is not correct and as this function is not that reliable I already said that this may be a wrong info.
But even if there would be water - in my opinion that won't be really spectacular as when you handle chemicals there is always a little residue of any stuff which was in contact with your substance during the process - like an Acetone peak when you don't really dry your NMR-Vial after washing it with Acetone. But I'm pretty sure that there should be no water as I dried it with MgSO4 before evap.

Hehe why did you post those other PDFs ?

So that I shall read them to understand basics of NMR ?

But didn't I just post a complete analyzed NMR-Spectra O:
Well for the question for the purification:

Yeah there was none at all like you said. Just the Toluene Pulls evapped in vacuum ... which gave that oil.

And yeah HPLC is a nice friend to have, but why should I do it o_O

Of course it will give a purer product. But I just wanted to share the NMR of the substance which I extracted by using completely no re-x / defat and Toluene instead of Naphtha.

The NMR shows that there are so less contaminations that I can clearly say this compound does not need any workup - ONLY if you want to have it crystaline and not as an oil.

This was even the target to get a nice compound with the least amount of steps or work, therefore why doing a HPLC just to be really really really sure about purity = D (which is also expensive if you had to pay it on your own and if not, then you will be using an illegal substance in a public laboratory which is also a little bit risky)

EDIT: Also you say I should do the HPLC and then re-run the NMRs. Well I may have crystals and not oil, but what change should that make for the resulting NMR Spectra?
Unfortunately, the administration keeps a tight noose around the groovier details of organic chemistry and spectroscopy. I would suggest posting your concerns, results and inquiries at sciencemadness.org as the community over there is far better equipped to further entertain this discussion, and are better equipped and freely able to discuss organic chemistry with you.
Well ... I don't really know where your point is.

Just in short again:

I just created some Spice at home. I did a lazy tek which is focussed on pulling the maximum amount of spice, even when getting more contaminants.

Now I just did an NMR on the outcome to have an estimation how pure it is.

--> The oily Substance is showing NEARLY ONLY the signals of that which DMT should show.

This is satisfying for me as I now know, that there is no real contaminant or at least no contaminant in a quantitative amount.

And yes - Water can bind everywhere and is in a lot of NMR present which you normally proceed when being a Chemist. Maybe there is water left in there, maybe not - but that's not really interesting.
And I did the analysis on a unpurified product - yes. But then WHERE is the multiverse of other contaminants, which skewed my results ad infinitum? I cannot see any ?!

You say that the simple 1H/13C NMR of the soup will give an incoherent mess of conjumbled peaks. What ? I HAVE done it and I have POSTED it here. There is NO incoherent mess of conjumbled peaks. This is actually the point that I want to tell others with this post.

= NO incoherent mess of undescribable peaks

Just the peaks which are clearly belonging to the DMT Molecule.

And how are my results inconsistent? And how can a NMR measurement be infoluenced by human errors? The process is fully automated and even if there would be human errors, how should they look like in my spectra? I mean the

- chemical shift is perfect
- integrals are perfect
- multiplicity is as predicted

"Jamming a sticky unrefined goo into an NMR spectrometer will give you nothing but a cacophony of incoherent signals"

-> I got exactly the DMT-signals and all of the other signals in the complete 1H spectrum combined have an integral of ~ 3,6. The total integral of the DMT signals is 15. Within some synthesis which I had to do in the past I even used compounds which were containing much bigger amounts of inexplicable signals.

" ... then jammed it into an NMR spectrometer expecting picture perfect results."

I did not expect perfect results, I expected a mess. Then I looked at the results. And the results ARE perfect. I did not expect them to be, but they are!

Please tell me what exact signals in this Spectra is belonging to your described incoherent mess of conjumbled peaks ... :?:
Yes I read this, but of course this is new stuff, as this is analytics done with NMR, which is by far the most common method of checking out any organic compounds.

Sadly the thread got a little messed up within the first posts.

I will just do a little summary about what I wanted to say here:

METHOD = I did a method for max yield and left out purification steps, also the use of Toluene instead of Naphtha

PREDICTION = The oily substance will be a mixture of DMT and a varying lot of other stuff, fats and even unknown substances, which will decrease the real purity of my DMT

OBERSATION (of the NMR) = Nearly NO quantitative contamination, the signals of DMT itself are perfecty visible and also with the correct chemical shift / multiplicity / integrals

CONCLUSION = As we dudes want to extract DMT and (possibly) create Changa with this, the compound which I extracted is perfectly fine for this. There are NEARLY NO other signals, which indicate that my oil is indeed mostly DMT by far. Anything which would have made the oil more pure would have possibly also decrease the total amount of DMT, as purification is always also decreasing the total amount of spice gained.

Therefore I just want to state my point that the use of any other purification methods would not have led to a better changa at all.
I don't know why there was this discussion in the beginning of the thread, I just want you to know that if you trust a person who does chemistry business since years, this compound is really nearly pure.

If you have any questions how to understand those NMR Spectra or what the Tek was feel free to ask.
Both you and burnt come to the very same conclusion using different methods :thumb_up: :love:
Each month a newb comes asking here at nexus to clean up some colorization because they think it must be white to be dmt ;)
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