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DMT N-Oxide to Freebase DMT Options
 
benzyme
#61 Posted : 12/8/2012 8:35:03 PM

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what means of characterization is being used to determine that reduced dmt is obtained?
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GordoTEK
#62 Posted : 2/19/2019 1:39:39 PM

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I know this thread is quite old, but I have a related question I can't find an answer to... DMT N-Oxide is described here as a yellow oil, but when nice clean pure white N,N-DMT freebase just sits out in the open air for years, it becomes oxidized, and changes color from white (original) to pinkish\red. Can anyone explain how/why DMT N-Oxide can be both a pinkish\red powder and a yellow oil? Are these actually two completely different things? If so, what exactly is the chemical difference between these two forms of DMT?
 
benzyme
#63 Posted : 2/20/2019 1:17:03 AM

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I've done LCMS analysis on yellow oil, and red oil. both show up as 189 for the base peak, but no prominent 205 peak.

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Loveall
#64 Posted : 2/20/2019 1:40:53 AM

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For what it is worth, I've vaped aged FB that had turned red and could not detect a difference in effects.
“... (a) psychedelic substance occasionally causes psychotic behaviour in people who have not taken it.”
Excerpt from a McKenna talk transcript / audio.
 
benzyme
#65 Posted : 2/20/2019 2:22:33 AM

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I suspect the depiction of DMT N-Oxide on Wikipedia is incorrect. The pyrrole amine (a secondary amine) is more susceptible to autooxidation than the terminal amine, which is a tertiary amine; it's the reason for the ochre color of tryptamine and its derivatives.
"Nothing is true, everything is permitted." ~ hassan i sabbah
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Brennendes Wasser
#66 Posted : 2/21/2019 7:03:27 PM

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Could be that the oxygen is linked to that secondary Amine, but at least at my test sample which sat in the sun for ~ 2 days the NMR proves that it is only that amine in the chain.

Gonna have to test a sample which stood in open air at a window for more than half a year now, checking if I got more than 11 % conversion to N-Oxide and also possibly if that other amine was oxidized by now. Sadly the sun hasn't been strong the last 5 months of course so half a year will not be half a year UV-exhibition x_x

As for the colour:

No clue why you mean that your N-Oxide (if it was some) got red/pink.

My N-Oxide after 2 days = orange
and
My N-Oxide after half a year = orange-brown

so it just fortifies its dark brownish colour over time ... never read something about pink ones.

What would be really interesting (if nobody has done it before, which I would doubt):

During summer, place some Spice in the sun and really flatten the material, so that it should get the most UV rays possible during a short time and then try to vape it. Maybe you would get more than 11 % conversion if you really flatten it out during just a few days so it would be fast to test it.
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
pastanostra
#67 Posted : 2/21/2019 8:59:17 PM

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Half a year ago i've done and extraction with xylene on Simplex.
Classical AB, evaped xylene, resulting extract was yellow, from my other results i suspect it to be mainly DMT.
It has been stored in the same plate on the picture, with a plastic wrap, at room T°, and in the dark (in a shelf without sunlight))

Afterfew month let here, the extract turned red/orange as in picture.
Did not tested (and bioassyed) the extracts.


https://imgur.com/a/nhg6LXB

Idk if this could help, but sunlight seems not be the only factor that change the extract color, at least, for my experiment. The extract smeel the same as freshly extracted (floral smells).

On the same bark, while backsalting the xylene with vinegar, then pulling with acetone, the resulting extract is a brown resin, that did not change in color or smell after month, it stayed brownish and floral. It was stored at the same place and factor than the precedent extract.

https://imgur.com/a/6F9xo69

Peace Guys Smile

 
benzyme
#68 Posted : 2/22/2019 1:41:40 AM

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the color change is due to pyrrole autooxidation (in air).
"Nothing is true, everything is permitted." ~ hassan i sabbah
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benzyme
#69 Posted : 2/22/2019 1:41:47 AM

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the color change is due to pyrrole autooxidation (in air).
"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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endlessness
#70 Posted : 2/22/2019 11:33:36 AM

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Benz do you have a sketch how that molecule would look like? Does it fragment with MS similarly to the n-oxide?

When tested with GC-MS the reddish oxidated DMT, there was still mostly DMT, with a very small amount of what seemed to be DMT N-Oxide. Maybe some of the n-oxide might turn back into DMT with GC-MS, LC-MS would be more appropriate, I can try again once I have access to the LC-MS again.

I suppose NMR could help differentiating the two types of oxides right?

Brennendes Wasser will you do this test soon? I'd be very interesting in hearing the results
 
Mindlusion
#71 Posted : 2/22/2019 3:51:54 PM

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the concentrations are probably too small to detect by NMR.

Pretty much every colorless amine will turn yellow with exposure to air and light, and aromatic amines like pyrrole and aniline will often turn black. Though despite this discoloration, by NMR or GC-MS they are usually >99.5% pure, or at least, any impurities are so small they are negligible.
Expect nothing, Receive everything.
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"The most beautiful thing we can experience, is the mysterious. The source of all true art and science."
 
Brennendes Wasser
#72 Posted : 2/22/2019 5:42:48 PM

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Mindlusion wrote:
the concentrations are probably too small to detect by NMR.


Well at least the ratio of the *regular* N-Oxide was clearly visible as 11:89 within that sample. And it was only standing in UV Exposure for ~ 2 days.

So what Benzyme means should look like this I guess:



And if you take a look at my sample it seems that there is only the *regular* N-Oxide:

Aromatic Signals are all at its place -> no shift caused by a potential O inside that cyclic structures - or at least nothing that would be distinguishable from signal noise Oô




Yeah ... I should measure that long-term sample and other stuff that is waiting for it. But sadly my university life has changed so I am not having regular access to all of this nice analysis stuff : \ Otherwise I just could provide it tomorrow. Gonna have to see when the next stuff will be coming.
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Mindlusion
#73 Posted : 2/22/2019 7:59:52 PM

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Brennendes Wasser wrote:
Mindlusion wrote:
the concentrations are probably too small to detect by NMR.


Well at least the ratio of the *regular* N-Oxide was clearly visible as 11:89 within that sample. And it was only standing in UV Exposure for ~ 2 days.

So what Benzyme means should look like this I guess:



And if you take a look at my sample it seems that there is only the *regular* N-Oxide:

Aromatic Signals are all at its place -> no shift caused by a potential O inside that cyclic structures - or at least nothing that would be distinguishable from signal noise Oô




Yeah ... I should measure that long-term sample and other stuff that is waiting for it. But sadly my university life has changed so I am not having regular access to all of this nice analysis stuff : \ Otherwise I just could provide it tomorrow. Gonna have to see when the next stuff will be coming.


yes the tertiary N-oxide is visible by NMR for sure, if you leave it in the sun for a few days.

What I was getting at is that in most cases you cannot detect what the discoloration is by NMR or even GC-MS. It seems only very trace quantities can greatly discolor the material. What benzyme is getting at about the N-pyrrole is due to the fact that tryptamine itself and other indole molecules that are not also tertiary amines, discolour rapidly to the same yellow orange/ochre colour. My point about various heterocyclic and aromatic amines like indole and pyrrole themselves will quickly discolour to the same ochre or even black. Neither of which can not be the result of the tertiary N-oxide.

The molecule you have drawn for the pyrrole n-oxide doesn't exist, it would have to exist as a hydroxylamine. Pyrrole n-oxides only exist in the form of the iminium resonance structure... a reactive intermediate. Neither of which is seen in your NMR spectra. More likely the cause of the discoloration is a result of byproducts of the N-pyrrole oxidation. Traces of oxoindole dimerization or polymers perhaps.

in short, the point is that discolouration =/= n-oxide, and whatever the exact molecule or set of molecules the discolouration is a result from is not exactly understood in detail
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benzyme
#74 Posted : 2/22/2019 8:31:20 PM

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yea, I should've been more specific...
I read somewhere the coloration is due to the pi-bond character in the pyrrole, and yes, it is poorly understood.

I just recently did a decarboxylation of alpha-methyltryptophan with acetophenone, but not under inert atmosphere. the
solution quickly turned from white to dark amber, and the product was purple crystals, with a base peak of 177 m/z (M + 3), no N-Oxide peak.
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Brennendes Wasser
#75 Posted : 2/22/2019 9:26:19 PM

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Quote:
dmt oxide is just a little oxygen stuck on the bottom right there


The picture above is NOT the 'real' N-Oxide - it is located at that other N.

And yes - as it will change the electronic properties and also its biochemical interactions , thus it may be not that active as DMT - even though people say it is just as active - but still at least I would say we don't know if that *just as active* was because of residual Spice content and the N-Oxide maaay still not be active, or is it reported that one ingested pure N-Oxide?

Also just based on the formula I really would not imagine that this thing is likely to evaporate easily ... I mean even Bufotenine seems to have a much higher vaporization temp than regular spice, think I read somewhere ~ 145 °C ? Oô.

Maybe if someone vaped a mixture of like 10 % degraded Spice and vaporized 90 % of it, then the N-Oxide was not vaporated and he still got that effect of the residual 90 % spice?

Quote:
Neither of which is seen in your NMR spectra


yes thats what I wanted to say - at least in terms of relevant amounts it seems that the classic N-Oxide was the main oxidation product.


I also asked an Organic Chemistry Professor like 1 year ago about that Amine coloration. I was more unspecific and did not ask about Indoles directly. Therefore I hoped that there may be more answers, but the outcome was not that satisfying ...

Except that he said the general coloration of Amines upon exposure of Oxygen (and possibly light) isn't that well understood, he said some guys think it is caused by the formation of a high-molecular structure between those amine compounds ...

Don't know if that is a real thing or if he just wanted to give an answer at all Confused Big grin As an example he gave Aniline I think but I dont remember ...

Maybe gonna ask someone else in hope for another answer Wut?
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Mindlusion
#76 Posted : 2/22/2019 9:33:37 PM

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Brennendes Wasser wrote:
Quote:
dmt oxide is just a little oxygen stuck on the bottom right there


The picture above is NOT the 'real' N-Oxide - it is located at that other N.

And yes - as it will change the electronic properties and also its biochemical interactions , thus it may be not that active as DMT - even though people say it is just as active - but still at least I would say we don't know if that *just as active* was because of residual Spice content and the N-Oxide maaay still not be active, or is it reported that one ingested pure N-Oxide?

Also just based on the formula I really would not imagine that this thing is likely to evaporate easily ... I mean even Bufotenine seems to have a much higher vaporization temp.

Maybe if someone vaped a mixture of like 10 % degraded Spice and vaporized 90 % of it, then the N-Oxide was not vaporated and he still got that effect of the residual 90 % spice?



It is active, I synthesized some and tested it. It was active but without the psychedelic effect of DMT. But my simple test isn't a true measure by any means. And the vaporization products could just be decomposition products.


Brennendes Wasser wrote:

I also asked an Organic Chemistry Professor like 1 year ago about that Amine coloration. I was more unspecific and did not ask about Indoles directly. Therefore I hoped that there may be more answers, but the outcome was not that satisfying ...

Except that he said the general coloration of Amines upon exposure of Oxygen (and possibly light) isn't that well understood, he said some guys think it is caused by the formation of a high-molecular structure between those amine compounds ...

Don't know if that is a real thing or if he just wanted to give an answer at all Confused Big grin As an example he gave Aniline I think but I dont remember ...

Maybe gonna ask someone else in hope for another answer Wut?


Yes this is what I just stated as well. Don't expect to find an answer that is more than the usual speculation, maybe do some digging in the literature you might find something.
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Brennendes Wasser
#77 Posted : 2/22/2019 9:40:24 PM

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Quote:
It is active, I synthesized some and tested it. It was active but without the psychedelic effect of DMT. But my simple test isn't a true measure by any means.


Ok well at least this test was successfull, so it has a real effect. But what I am really wondering about:

Considering the structure of Spice every functional component should be important for its biochemical recognition / effect resolving and so on.

And as an amine is totally different from an N-Oxide, how does this even work?

I mean if I remember it correctly then it was told that the charged / polar groups are the first ones to start the initial process of a ligand binding to its target. As ionic substances have the longest distance interactions, normally they are used first to make the molecule approaching its enzyme / protein / whatever (only if present at the ligand of course), afterwards any regular polar groups start to interact. Stuff like aromatics start interacting at the shortest distance any mainly keep the ligand sticking correctly at the binding site.

So if alterating a charge of a ligand its metabolism should normally be changed by far or at least the binding should be affected a lot!

Now if we alterate that chain in Spice I would normally expect the molecule to be inable to conduct its normal binding mechanism, that it would definetly not bind or not that strong.

I mean yes ... that positive and negative charge is quite in a short distance and it should not result in a strong dipol moment. But still: The amine completely loses its nucleophilic ways of interaction and that Oxygen(-) should greatly push it away from places that it may have interacted before.

So ... I would just have assumed that this would totally block it from getting where it was before. But seems not Confused Surprised Big grin



EDIT: that orange colour truly does not only arise upon oxidation - I guess a lot of people also have heated their white spice to a brown liquid and upon cooling it remained brown ...
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Mindlusion
#78 Posted : 2/22/2019 10:27:34 PM

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Brennendes Wasser wrote:
Quote:
It is active, I synthesized some and tested it. It was active but without the psychedelic effect of DMT. But my simple test isn't a true measure by any means.


Ok well at least this test was successfull, so it has a real effect. But what I am really wondering about:

Considering the structure of Spice every functional component should be important for its biochemical recognition / effect resolving and so on.

And as an amine is totally different from an N-Oxide, how does this even work?

I mean if I remember it correctly then it was told that the charged / polar groups are the first ones to start the initial process of a ligand binding to its target. As ionic substances have the longest distance interactions, normally they are used first to make the molecule approaching its enzyme / protein / whatever (only if present at the ligand of course), afterwards any regular polar groups start to interact. Stuff like aromatics start interacting at the shortest distance any mainly keep the ligand sticking correctly at the binding site.

So if alterating a charge of a ligand its metabolism should normally be changed by far or at least the binding should be affected a lot!

Now if we alterate that chain in Spice I would normally expect the molecule to be inable to conduct its normal binding mechanism, that it would definetly not bind or not that strong.

I mean yes ... that positive and negative charge is quite in a short distance and it should not result in a strong dipol moment. But still: The amine completely loses its nucleophilic ways of interaction and that Oxygen(-) should greatly push it away from places that it may have interacted before.

So ... I would just have assumed that this would totally block it from getting where it was before. But seems not Confused Surprised Big grin

.


well that's the point as well. Obviously the N-oxide wont have anywhere close to the binding profile of an amine. I don't think the N-oxide is active, probably just thermal decomposition products, or trace dmt, or perhaps metabolically some is converted back to the amine.


Quote:
EDIT: that orange colour truly does not only arise upon oxidation - I guess a lot of people also have heated their white spice to a brown liquid and upon cooling it remained brown ..


well... they heated it in a 20% oxygen atmosphere....
Expect nothing, Receive everything.
"Experiment and extrapolation is the only means the organic chemists (humans) currrently have - in contrast to "God" (and possibly R. B. Woodward). "
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"The most beautiful thing we can experience, is the mysterious. The source of all true art and science."
 
Brennendes Wasser
#79 Posted : 2/22/2019 10:32:28 PM

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Yes but at least my sample does not show ANY signs of oxidation ...

Again just mostly Spice and still brown Confused

Maybe this could be achieved:

make a HUGE hill of spice inside the oven, heat it to 100 °C (only some minutes seem to do it if not less) and then recrystalize all the stuff, keeping the plain spice (as it will mostly be, obviously) and use everything that did not dissolve or stays in solution for a sample.

Even if there is only 1 % of that brown thing forming, LC-MS will be able to tell something interesting or even NMR, but then I guess 1 or even 5 g would be needed to produce enough of that brown rubbish Neutral
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Mindlusion
#80 Posted : 2/22/2019 10:37:27 PM

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Brennendes Wasser wrote:
Yes but at least my sample does not show ANY signs of oxidation ...

Again just mostly Spice and still brown Confused

Maybe this could be achieved:

make a HUGE hill of spice inside the oven, heat it to 100 °C (only some minutes seem to do it if not less) and then recrystalize all the stuff, keeping the plain spice (as it will mostly be, obviously) and use everything that did not dissolve or stays in solution for a sample.

Even if there is only 1 % of that brown thing forming, LC-MS will be able to tell something interesting or even NMR, but then I guess 1 or even 5 g would be needed to produce enough of that brown rubbish Neutral


I already described this in my previous post. The whole point of the post was show that difference.

The brown colour ISN'T N-Oxide. But it is STILL an oxidation byproduct, coming from the indole ring. And its difficult to quantify. Its likely not a single compound but many of higher molecular weight, dimers polymers, that kind of mess. You can try.
Expect nothing, Receive everything.
"Experiment and extrapolation is the only means the organic chemists (humans) currrently have - in contrast to "God" (and possibly R. B. Woodward). "
He alone sees truly who sees the Absolute the same in every creature...seeing the same Absolute everywhere, he does not harm himself or others. - The Bhagavad Gita
"The most beautiful thing we can experience, is the mysterious. The source of all true art and science."
 
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