What are the current views, facts and theories on DMT-N-OXIDE?

[q21q21]

Now I have in Q21Q21's tek my theory about the yellow in freezer-precipitated DMT and I have posted it a few times without response (agreeing or otherwise. But this is a forum and this happens all the time, this is not what this is about.)

My current theory in short is:

Assuming minimal contamination of MHRB and/or lye-water in the DMT, which can cause the DMT to take on a yellow, orange or brown color (to the best of my knowledge). This I believe to be in such cases where a recrystallization in naphtha or acetone or some other method was used to clean the DMT product to this point.

Assuming that, I conjecture it is more likely that the majority of any yellow color in the DMT is not DMT-N-OXIDE but rather the "Jungle Alkaloids" which when dissolved in dilute vinegar are pale yellow and only change to reddish-orange then red-brown when very concentrated.

I believe that DMT-N-OXIDE is likely to be present but in insignificant quantities to affect the quality of the DMT's effects.
While DMT left out for long periods of time can take on a yellow color (or increase in yellow-ness) I don't believe if it is enough to effect the product's effects.


I put this theory forth in a thread in May 2010 and though it seemed that many accepted this as a distinct possibility, the furthest one can really go with a theory like this one without testing.

SnozzleBerry put it quite well:

There's really no way to say authoritatively what the composition of this is without GC/MS readings, imo.

Nonetheless I continue to see "fears of DMT-N-OXIDE" threads and posts coming quite often with many unlikely-to-be-true claims as responses.

Personally I would really like to hear any opinions on the theory. Opinions and rebuttal opinions alike.
Maybe someone could get some GC/MS readings on washed yellow-DMT and unwashed. (I don't even know what GC/MS stands for without looking it up though)

Regards,
Q21Q21

 

[tele]

Yeah it's obviously important to discuss the Dmt oxide that so many talk about, but few know much about(me included). What I have found is that with q21's tek for example, the DMT that has waxy, not crystal consistency, turns yellow or even orange in a day or two. The leftover yellow/orange oils from re-x are a good way to investigate it. If it would be only dmt-n-oxide, it would be similar in effects to white DMT, when smoked.

I'm no expert but I hope we will get more knowledge about this matter...

 

[Entropymancer]

Well, burnt's chemical analysis seems to show that even deeply colored jungle spice contains mostly DMT, with only small traces of other compounds. So it's probably a mischaracterization to say that they "only change to reddish-orange then red-brown when very concentrated." Not to say that these traces don't have an effect... they could.

Unfortunately GC/MS cannot distinguish between DMT and its N-oxide, so simple TLC analysis is going to provide better data to resolve this point than GC/MS. I haven't really kept up on what sort of work people have been doing on DMT-N-oxide, so perhaps this issue has already been addressed? At any rate, I think the simplest way to resolve the question would be to perform TLC analysis of several samples of yellow spice (I don't have Trout's Notes in front of me, but I think it contains enough information to select a eluent system that can resolve DMT and its N-oxide, and for which Rf values have been reported in the literature). Then a zinc reduction (per literature) could be performed on each sample, and the products again analyzed by TLC. If there are significant N-oxide spots in the yellow samples which disappear in the reduced samples, that would pretty clearly show that DMT-N-oxide is significantly present. For controls on the TLC analysis, you could use clean white DMT along with DMT that has been oxidized with hydrogen peroxide (again, per literature).

 

[nen888]

q21q21 posted in yellow oil DMT-N-Oxide orally active?

I used peroxide on pure-white DMT to produce a yellow oil which I manually crystalized into this(see photo attatched below..Nen)

It went back to an oil after 30 minutes or so. 40mg was smoked with mild DMT-like effects, about 1/4-1/3 the effects of White DMT.
The other test I mentioned above:
"A while ago I tested N-oxide made with peroxide at a low dose, like 40mg I think, and the results were very similar to the same doses of white DMT with mild effects definately different than just harmalas."

Also, something I feel compelled to say:
I don't think you should assume the yellow is DMT-n-oxide. I know that Naptha dissolves about 6-9% (estimate from tests) jungle DMT (and 91-94% White DMT) Having evaporated vinegar with jungle DMT in it many times I know it is pale yellow when diluted. With that I strongly believe that MOST of the impurities in yellow DMT is not DMT-n-oxide but rather Jungle DMT (which is liquid).
Sure there is probably some N-oxide in there but I believe oxides are mostly in very insignificant amounts, too low to affect the effects.
This explains why many prefer the effects of yellow DMT which should be just much weaker were the yellow DMT-n-oxide.
(tired now, pardon the incomplete argument. I'm sure you get the point though)

so the yellow oil may not be DMT-N-Oxide..i didn't find NMT to be orally active at 40-50mg (no MAOI), but i'll try again (was active with MAOI)..so the oil could be something else again...
(here's q21q21's DMT-N-Oxide photo)

 

[q21q21]

Yes, I did do that test but I pretty much discredit any of my bio-essays of anything but smoking DMT or eating mushrooms which are the ONLY things that give me reliably consistent results. Pharmahuasca and Mimosahuasca being particularly unreliable for me.

The physical properties of the test, use them.
Subjective testing, take it with a grain of salt.

 

[nen888]

..your mystery 'jungle alkaloid' , q21q21,could be Yuremamine, believed psychoactive and possible MAOI, found along with tryptamine and serotonin in MHRB in published studies (see S. Voogenbreinder Garden Of Eden)..
the properties of all three compounds need some further clarification for TLC and reagent tests...

 

[endlessness]

Not really nen, because yuremamine is broken down during extraction conditions (heat, basic pH and IIRC acidic too). I can pull up the reference on sunday, im about to go camping for the day/night. Its from Callaway.

Only a cold water soak or a methanol/ethanol soak and evap, would yield yuremamine

 

[polytrip]

I once took ayahuasca made with very old chacruna. The experience wasn't much different than an experience with fresh chacruna would have been, except for the fact that for the first few minutes i only had strong visual effects without any other effect. I think this was because of DMT-n-oxide. I have the suspicion that it is very close to DMT but just a bit more visual.

 

[nen888]

yuremamine is broken down during extraction conditions (heat, basic pH and IIRC acidic too).

..thanks endlessness, i don't have any data on the alkaloid myself, would be good to see some references..
..there's still possible tryptamine &/or serotonin, isn't there..?

re: DMT-N-Oxide, a few reputable nexians have said that it is as potent, if not slightly more than DMT, when smoked..earlier writers claimed non activity or 10x reduced potency..
i wonder why the discrepancy?, but i suppose about as much work has been done on it as nmt...

 

[q21q21]

@ nen888

You know the one test that I did do, twice, which was very significant were:
1:Smoke both those crystals seen above, produced from manual crystallization after dissolving white crystals in peroxide and acetone (appearently unsafe)
2.Exactly the same but using only peroxide (forget if it dissolve or just sat at the bottom) evaporating the smoking.
First time was 15mg, the second was 20mg. These chosen because I was about 3x more experienced with these doses on full-spectrum and white DMT than 30+mg doses.

Both times were very consistent and very significant. I started to smoke and I got the same mild body-high from smoking DMT, or anything then when I looked for visuals or tracers they just didn't come.
Even 20mg while producing a lot of smoke (vaped/smoked in a "machine" bubbler) gave maybe mild tracers and the faintest shapes in CEVs.
20mg of Full-spectrum or white DMT reliably (more than 2 times for sure!)produced significant OEVs, CEVs, tracers and often entities.

I would love to see this repeated! Just dissolve *x*mg DMT in peroxide (I think I use the 3% in the bottle) then evaporate, scrape up and smoke it.
This could be done I suppose in 1 hour and in 2 different orders. Oxides first, wait 30 minutes, White DMT then swapped on another day or maybe only several hours later.

What do you guys think?

 

[endlessness]

Nen, the paper I mentioned is:

Isolation and characterization of yuremamine, a new phytoindole - PubMed

Yuremamine was isolated and characterized from the stem bark of Mimosa tenuiflora. This plant is still used by indigenous peoples in North-eastern Brazil to make yurema, a psychoactive beverage that is used for medico-religious purpose ( jurema preta or vinho da jurema, in Portuguese). The...

www.ncbi.nlm.nih.gov

and it says:

Initially we applied standard acid-base extraction methods to
the stem bark sample, which resulted in a wide variety of com-
plex, unidentified degradation products. Compound 1 is clearly
unstable, which may account for the identification of only DMT
in previous phytochemical investigations of both M. hostilis and
M. tenuiflora when using basic extraction conditions during sam-
ple preparation. The earliest phytochemical analysis of this
Mimosa species (as Mimosa hostilis) identified only one alkaloid,
which may or may not have been DMT [2]. The proposed struc-
ture in Fig. 3 also explains the chemical instability of this mol-
ecule, especially under basic conditions.

Here's the structure of fig 3

(interesting how it has a dmt molecule in it's structure)

So only a cold water/alcohol soak would get yuremamine without degrading it.


Maybe we should add it to the psychedelic compounds properties wiki.

As for N-Oxide, this paper talks about trying to find dmt n-oxide in ayahuasca brews and did not find any. Maybe one could have expected that with 10h brewing there would be at least some n-oxide formed (plus viridis being a leafy plant and one would imagine more oxygen than in the roots of mimosa?), but apparently not.

In Trout's book simple tryptamines, it is mentioned that DMT N-oxide is not soluble in pet ether ( = naphtha) when pure but it IS soluble in pet ether in the presence of other plant fats (the fats seem to help dissolve the n-oxide ...)

Several papers cite the formation of n-oxide with hydrogen peroxide, for example

"50mg of dmt dissolved in 2ml ethanol was treated with 2ml H2O2 (1ml of 30% H2O2 in 9ml. of ethanol). After 2 hours (at room temp) crystallization was induced by adding ether and chilling.

The granular DMT-N-Oxide was removed and recrystallized from ethanol-ether. N-Methyl Tryptamine (NMT) is not affected by the addition of peroxide."

above it says it can be granular recrystallized

Dmt n-oxide is said to be an oil (fish et al. 1956).

But also a hygroscopic solid (banerjee & ghosall 1969).

Trout references Fish et al (1955) to say dmt n-oxide is formed rather easily in dmt solutions exposed to air during extensive experimental manipulations, but this is the paper and i dont see anything about easy formation after extensive manipulation, maybe im just missing something?


DMT N-Oxide can be reduced back to dmt by mixing in an acetic acid solution and adding excess zinc, basing and re-extracting.

Q21, you should really look into TLC and colorimetric reagents, you could identify your substance.

 

[q21q21]

above it says it can be granular recrystallized

Dmt n-oxide is said to be an oil (fish et al. 1956).

But also a hygroscopic solid (banerjee & ghosall 1969).....

....Q21, you should really look into TLC and colorimetric reagents, you could identify your substance.

That is interesting, I mentioned in the original thread that the picture is from that although the product on the razor is seen as crystallized, it evaporated to an oil and went back to an oil in 10 minutes or so from the crystals.

As for TLC. Unlike it would be something I do. I realized when considering synthesizing GHB from GABA that I am no chemist and doing this stuff without the proper equipment is unwise. Not that TLC requires a lot but it is just that without background education (only 11th grade Chemistry) a lot of the stuff goes over my head.

 

[nen888]

thanks endlessness,
wira sent me the following message:

Regarding yuremamine, hopefully these snippets have what you need -
On HPLC - "For the preparative runs, the retention time for the compound of interest [yuremamine] was 12.9 minutes (k' = 10.1), and 16.3 minutes (k' = 13. for analytical runs."
On LC-MS - "retention time of 12.9 min (k' = 7.6)."
"A measured accurate mass of 477.2041 corresponded well with an elemental composition of C27H29N2O6 (calculated 477.2026)."
Yuremamine is 1"-[1-(2',4'-dihydroxyphenyl)-9-(2-dimethylaminoethyl)-2-hydroxy-2,3-dihydro-1H-3a-azacyclopenta[a]inden-1-yl]benzene-3",4",5"-triol. Phew!

q21q21, you wrote

I mentioned in the original thread that the picture is from that although the product on the razor is seen as crystallized, it evaporated to an oil and went back to an oil in 10 minutes or so from the crystals.

..i suspect many 'oils' infact have small mixtures of other alkaloids..subjecting the pictured material to paper chromatography (see "entheogenic effects of NMT p.3 for example proceedure) and re-X would, to me, seem the next logical step...

 

[endlessness]

Hey Q21, did you check the link about TLC? Its actually quite simple process, and so is paper chromatography. If there's anything in you dont understand in my explanation, feel free to ask for clarification

Nen, I just edited my previous post, to add the publication link (if you want i can pm you the full text, i wont post here because it appears the name of my university on the pdf when I download it

By the way, can you ask wira where that information is from?

 

[nen888]

..hey q21q21, if you're capable of extracting dmt and converting it to the oxide, you are quite capable of performing Paper Chromatography..read post #25 (p.2) here:entheogenic effects of NMT, also you can experiment with the solvent mixtures given here:chromatographic properties of n-oxides (post#11 by endlessness)
..by playing with the angle of paper/glass 'column', and the solvent mix, it shouldn't be too hard to get usable results..this is how chemists did it prior to the '60s...
..my chemistry education is no better than yours q21q21, for me it's about thinking for oneself, not having stuff shoved down one's throat (as at school, university)
..and finally, reagents can be commercially purchased, but are often not hard to prepare..
you wrote:

I would love to see this repeated! Just dissolve *x*mg DMT in peroxide (I think I use the 3% in the bottle) then evaporate, scrape up and smoke it.

great idea, but it would be good to confirm the reaction is being done to fairly pure DMT (again, reagents)

endlessness it is indeed

(interesting how it has a dmt molecule in it's structure)

as you commented..complex 'hyper-tryptamines' have also been found in some New Guinea and Australian plants, will post on this in advanced chemistry soon..i wonder if all the dmt in the plant is initially contained within the yuremamine..other plants (which have only been tested with basic extraction) may also contain such compounds, making them potentially orally active in cold-water extractions...

 

[endlessness]

Very interesting nen! I am definitely looking forward to your post!

 

[nen888]

..getting those references together endlessness,

q21q21, i have pondered this regarding DMT-N-Oxide..
synthetic pure DMT turns increasingly yellow>orange over time..this is usually said by chemists to be oxidation..a ten year or more old sample that was very orange appeared to have lost no potency whatsoever..so, either the coloring oxide is only present in small amounts (as you suggested), or DMT-N-Oxide is as potent as DMT..
..i predict (but don't know) that the oil is a mixture of DMT & it's oxide, and that the pure oxide would be a solid...
.

 

[tele]

..getting those references together endlessness,

q21q21, i have pondered this regarding DMT-N-Oxide..
synthetic pure DMT turns increasingly yellow>orange over time..this is usually said by chemists to be oxidation..a ten year or more old sample that was very orange appeared to have lost no potency whatsoever..so, either the coloring oxide is only present in small amounts (as you suggested), or DMT-N-Oxide is as potent as DMT..
..i predict (but don't know) that the oil is a mixture of DMT & it's oxide, and that the pure oxide would be a solid...
.

I have noticed that slightly off-white DMT from limetek extraction can turn slightly orange after about 2 weeks. Is this normal or should it turn yellow? It was kept in a jar inside a ziplock bag with a decissant.

 

[nen888]

..tele, most 'really pure' dmt i've ever seen is pale yellow (after, presumably, a few weeks or more)..


i also wonder if the oxide displays any polymorphism (see dimethyltryptamine polymorphism? (& colour) (chemistry question))

here's an old thread on Mycotopia about DMT-N-Oxide https://mycotopia.net/forums/dmt-spice/38366-dmt-n-oxide-freebase-n-n-dmt.html

and an interesting bio-assay report of it here: Comparing DMT to DMT-n-Oxide

endlessness..the reference for yuremamine's composition given by wira is: Vespålåinen, J.J. et al. "Isolation and characterization of yuremamine, a new phytoindole." Planta Medica 71 1053-1057
.

 

[q21q21]

I have definately noticed this tendancy but check this!

A vinegar tincture made from just rinsing the precipitation container with vinegar (dissolving the film on the bottom, what I believe is jungle DMT) produces a pale to medium yellow liquid
Dissolving pure white crystals produces a super-pale yellow liquid (like a couple drops of apple juice in a shot)

Now the first one after a few months would be brownish-yellow. As dark as my jimjam tincture, just yellow-brown instead of red-orange.

the second on the other hand acquired nearly no extra color. It may have been a little more yellow but barely noticeable.

I don't know if that helps or whatever, that is just my experience.