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

[nen888]

..nmt seems to turn increasingly (dark) orange over times (can be initially white), it isn't (to my knowledge) yet recorded from M. hostilis (but is from M. opthalmocentra (with dmt)...simple tryptamine, however, has..it is recorded as pale brown needles or prisms becoming dark brown over time..[it's activity is not totally understood..it was found (by, i think, Sazra) in the '60s to be a very fast acting psychedelic when injected in large amounts (will attempt to find reference), there is also some evidence that the occurrence of tryptamine, in some vaporized extracts (of other plants), changed or slightly modified the subjective effects..]
..serotonin (5-hydroxytryptamine) has also apparently been found in traces in M. hostils..not sure of it's x-tal colors..could it be purple?..bufotenine (dimethyl-serotonin) is recorded by J. Ott as brown crystals with a shiny hue..
the only other fairly common tryptamine i can think of (other than 5meo which should be more obvious in small doses) is: 5-methoxytryptamine - potentiates sedatives, more active than serotonin [Bhudavari et al. 1989], oxytocic, natural trace component of human urine.. (properties?)
..ß-carbolines (such as harmine, harman or 2-meTHBC) often turn red in solution or upon solidification, or browny yellow, and can be altered by acids/heat etc.,or be by-products (as extraction artifacts) of simple tryptamines..


..now, DMT-N-Oxide..what it looks like is not yet widely established..it has not been chemically confirmed in any Mimosa species, only speculated..

q21q21, your 'jungle alkaloid' is probably may not be dmt-oxide
hope any of this is helpful in some way...

 

[nen888]

..afterword, ..endlessness tells me that NMT was detected in MHRB by nexian Burnt..
mimosa ophthalmoccentra is said by Ott and Voogelbreinder to have also been used as Jurema, and may simply be a variety of M. tenuiflora (hostilis), i will try to find out more..

 

[endlessness]

Hey nen,

Mimosa ophthalmocentra is most def a different plant than Mimosa hostilis. Ophthalmocentra is known locally as Jurema-Embira, while Mimosa hostilis is known as Jurema-Preta. There are a few ways to differentiate between both. The seeds are very different, here you can see some pictures of the small ophthalmocentra seeds and the pods, and compare them with the hostilis seeds and the pods here. There are other clear differences, as mentioned in this paper. The abstract is in english, the paper in portuguese. The paper is very interesting, has pictures and thorough descriptions. The problem is Im not sure how to translate certain botanical terms to english. It says, amongst other things (dont know if translated terms are correct):

The difference in the peel (outer bark) of both species is evident. M. ophthalmocentra (jurema-of-imbira) has
thin outer bark/peel, almost smooth, grayish-brown with yellowish lenticels (Fig. 3). M.
tenuiflora (Jurema) has thick, rough bark,with large lenticels and longitudinal grooves, easily releasing the rhytidome, and its color is dark, important feature that probably gave it the popular name of Jurema-Preta (...) the main morphological difference between both plants is the presence of "pontoações" (punctuations?) on the viscid-glandular abaxial surface of the leaflets of M. tenuiflora

Im also attaching this nice ophthalmocentra analysis paper that found DMT, NMT and hordenine:

Batista et al (1999) "Isolation and Identification of Putative Hallucinogenic Constituents from the Roots of Mimosa ophthalmocentra"

(all very offtopic, forgive me)

 

[tele]

I wonder what are the specks of yellow goo that hardens later on... I mean the product that comes sometimes with q21q21's tek after freeze precipitation. It does not crystallize, only comes as specks of goo that hardens after a day or two. It dissolves in acetone... Makes me think it's just dmt oxide?

 

[endlessness]

Could be n-oxide, could be NMT, could be just DMT that is trapped with some solvent traces or plant oils that prevent it from crystallizing. Could be a mixture of any and all of them. I think this will depend a lot on plant material, solvent of choice, heat of pull and so on, so I dont know how much we could generalize even if we get to analyze the material from one or other extraction.

 

[tele]

OK... I'm just wondering what it is as it's the first thing to precipitate, usually after about 1 hour after putting it into the freeza.

 

[nen888]

..thanks endlessness..
Johnathan Ott told me a few years back that another species was sometimes mistaken for M. tenuiflora (hostilis) in either Mexico or Brazil,
but i don't recall details..he's been a bit difficult to get in touch with lately i hear..
it would surprise me, given such a wide range of distribution, if there weren't genetic sub-types of M. hostilis (tenuiflora)
the paper you linked from Acta Botanica Brasilica does say:

Mimosa ophtalmocentra Mart. ex Benth. ("jurema-de-imbira" ) is confused with Mimosa tenuiflora (Willd.) Poir. ("jurema-preta" ) and vice versa

which is why they wrote the paper to differentiate..it's still quite possible the two species could hybridize to further muddy lines..
for the record here's Mimosa ophthalmocentra (native Brazil)
[EDIT: found to contain 3% tertiary alakloids in root bark! mainly DMT plus NMT & other traces]

 

[nen888]

..yeah, sorry to go off topic a bit, but i like to fill in the gaps..and eliminate what's NOT the oxide..

tele wrote (regrading yellow 'goo' that hardens)

OK... I'm just wondering what it is as it's the first thing to precipitate, usually after about 1 hour after putting it into the freeza.

..tele, a possible way of testing if it is (or mainly is) NMT would be to add a small amount of pure water prior to putting in the freezer..now, i don't know if this will work with whatever solvent you are using, but, as NMT is more polar than DMT, at the 'precipitation' stage you describe it can
mingle with the H20 (drawn to it), eventually becoming trapped in water-ice while the DMT crystalizes..upon removal the yellow should become liquid while the white DMT stays crystalized..if the NMT content is above a certain amount the DMT crystals can melt after a while,
but not always [this idea is drawn from experiments reported on p2 of entheogenic effects of NMT]..of course chromatography & reagents reveals more, but i've raved on about these lately already..if it fluoresces under UV a lot more brightly than pure-ish DMT, it could be a ß-carboline..

..BUT, i don't know a lot about how DMT-N-Oxide behaves, which is why i keep following
this thread..sorry to digress earlier

..someone out there must have more info..?
.

 

[nen888]

..here's an old thread of relevance..DMT n-Oxide Solubility in different solvents

..and below are two pics from shroomery, the first said to be DMT-N-Oxide, the second DMT freebase made by conversion of the previous pictured oxide..

 

[nen888]

..pure NMT begins as usually white/yellow, becoming eventually dark orange..Tryptamine is pale brown, turning chocolate.. (at least, from what i know)..betacarbolines are yellow/red/brown..the other arrays of colors and goos in 'jungle spice' may be due to plants containing oils; or likely alterations of molecules during A/B and heat manipulation, producing 'extraction artifacts' like ßcarbolines (often reddish) ;
or other alkaloids in the plant ('jungle alkaloids')

the shroomery-DMT-N-Oxide photo looks, to me, how i'd imagine the pure oxide of dmt would look..i predict it should be solid..in the earlier linked old oxide-solubility thread, 69ron says it's a goo, or oily, and likes it's effects, but i feel there must be a mixture going on here (with either dmt or other alkaloid)..then Phlux gets a little bit of an apparently solid dmt-oxide sample, but doesn't like the taste! ..then, it all ends abruptly with hush..

i think q21q21's oxide sample (photo p1.) is a mix of the oxide, some dmt and maybe ß-carbolines (a diluted red) & whatever the 'conversion' did to them.

 

[wira]

Just to clarify, Voogelbreinder didn't say that ophthalmocentra may be a variety of tenuiflora, and I don't think Ott said that either.
With the translation, I can't be sure but it sounds right. That could be 'punctations' but I don't know Portuguese. Translating botanical descriptions can be difficult (I've done a fair bit of it), but it looks like that translated pretty well apart from that one uncertain word.

 

[nen888]

..q21q21, i'm not in a situation to attempt to repeat your oxide experiment right now, or i would!
the shroomery oxide posting says:

Our starting point is DMT n-oxide, either the oil from a Bestine recrystallization, which many of us (myself included) have heretofore used "as is" (harsh and not a clean feeling high) or have simply thrown away in the past. What a shame! If you take the time to dry your n-oxide oil by leaving it out in an open shot glass for 24 - 48 hours, it WILL thicken and crystallize into a dirty yellow to brown tacky powder which you can then chop into crumbly, powdery bits as illustrated.

and a little chat in bluelight:

Q
"How does DMT degrade under intense, prolonged heat? Would said degraded compound be safe to ingest? Thanks."
skillet
"Intense, prolonged heat!? Such as what? Is it sealed from the air? Has it changed in appearance?"
sekio
"I'd expect oxidisation to N,N-DMT N-oxide and polymerization (to a total mess). Probably some indoleacetic acid, indoleacetaldehyde, dimethylamine, methylamine, ammonia, formaldehyde, CO2, H2O, methanol etc etc."

could the oil aspect be 'polymerization'? or does it simply need to be dried, as suggested in the first quote?
until you started this thread q21 i had no idea how not understood DMT-N-Oxide is, thanks...

 

[tobecomeone00]

All I know is it tastes like crap, and brings on something one could imagine as "hyperspace in HD", as if it weren't high defintion enough on its own...Not too pleasant, and I love me a mind-boggling journey...I consider myself a spiritualist, and from what is seemed like to me, was there was something else in this orange dmt that allowed the "entities" to contact/affect one much easier, almost on a physical level as opposed to within the mind's eye. It scared me, to be honest. It was as if the random entities had been brought into my dimension, as opposed to staying in hyperspace. In an totally un-scientific manner, I will attribute this to other plant oils being pulled into the naptha...Just my two cents. I didn't feel it as dangerous, just a bit jarring. lol.

 

[nen888]

..sounds interesting tobaecomeone00, on taste you agree with Phlux in the old thread..was the duration the same as a pure spice experience or longer?

q21q21 wrote:

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.

..i think you are probably right, q21! whatever those 'jungleloids' are.
..i'm still just a bit perplexed by your oxide sample effects/appearance vs. other reports (& i noticed the spice was white beforehand)
& the oil vs. solid thing (in both published & underground reports) is odd too...

 

[Dozuki]

I'm just going to jump in here and add my own thoughts, opinions, and opservations. First, without testing individual extraction results, its hard to even conjecture on what a compound may be that XXXExtracor ran across. This is why there is standardization and/or methodology included in the scientific literature. Even within the 'Teks' there should be standardization to at least pH and dilutions.

Assuming that the MHRB today is anything like it was 5 years ago, then I think that Yuremamine and its degradation need to also be taken into account as well. I would hedge my bets on this having to do more with 'Jungle Spice' than DMT-N-O.

Some years back I ran some plates on MHRB with the presumption that DMT was its only alkaloid. That was the thought at the time. When I ran my first plate I got three spots. This put me on a quest to try and figure out what the other spots were. There were 3 at first, but as that first extraction sat around one of the spots stopped showing up.

The first thing I looked into was the N-Oxide. I was interested in the 'Red' coloration associated with a lot of plants that contain Tryptamine Cmpds. My hypothesis was that the red coloration was due to oxidation. I still like to think that there may be something to this as well. So, I oxidized a sample of an extraction and compared that to the original sample with the anomalous spots. The oxidized sample created a new rf value, showing that what I was observing was not the oxidized product. (I'll give my lab notes on this procedure at the end).

About this time the paper on Yuremamine was published and I ran across Radio897(?)'s Mass Spec of an extraction that also showed an anomalous peak that was too heavy to be DMT. The Published Paper stated that yuremamine was not stable in alkaline conditions and showed the MS of the compound to be much heavier than DMT as well. These things led me to the conclusion that spots I observed were yuremamine and its degridation product.

I ran some more plates on 2 extractions done with room temp. water and methanol. These were both heavily tannin saturated and harder to deal with. The plates that I ran were in both acidic and basic elution solvents. The basic elution system always worked better with wider separations. On this plate, you could actually observe what appeared to be one of the spots disintegrating and forming another spot. I ran another plate in the same system but only to half the height, so that both spots remained. I would have ran it against the original sample except that the original sample was no longer showing this spot. It was conclusive enough for me to conclude that there were in fact degradation products of yuremamine in extractions using alkaline conditions.

At this point I did some experiments to try and deal with removing tannins from the MeOH extraction, and then kinda dropped it altogether as I was getting away from what I had originally set out to do (study wild stand of Phalaris).

Ox Procedure:

"4gm of sample taken up in 1ml EtOH. To this is added and [sic.] equal amount of 30% H2O2 containing etidronic acid as a stabilizer (Clairoxide 30). Solution becomes cloudy. This is allowed to react for 15 minutes with body heat (holding test tube in hand). Sample is chromotagraphed on Plate #4,5, and 6." (When this initial extraction was evaporated off is yielded a yellow oil that distinctly smelled floral.)

Plates #4 and #5 are are disregarded as the solvent system was a couple days old, plate #6 was ran in fresh solvent.

My notes on Plate #6:

"P6 is run in a different developer and would seem to show that the trace spot is not DMT-oxide when compared with the oxide sample (the oxidized one). The samples need run combined to see if there is separation or not (IE, that all samples combined show all the rf values, which according to Plate #8, they did). Also note that the blue spot in plate #2 is now not showing up. It needs to be determined is this is an anomaly or this cmpd. is unstable and disappears after 4 days. (This was before I read the yuremamine paper). Both the oxide lanes in Plate #4 are anomalous. These rf's did not show up in Plate #5. Color Development in Plate #4 is odd in that they are all rusty orange."

Also: Once a sample is spotted on the plate, it can be spotted again with an equal amount of 30% H2O2 to create the reaction directly on the TLC Plate. I did it both ways and came up with identical rf values. This is also a procedure stated in the literature on Phalaris, I believe. I don't think that 3% H2O2 is strong enough and should be at 30%.

Hope this helps

-D.

 

[nen888]

..interesting Dozuki,
the creator of the shroomery n-oxide (Nature Boy, occasional nexian i believe) describes it (see photo) as 'brown', i called the photo 'orange', but it maybe could be called 'red'..lol!
get me to a TLC set-up..!

how about 'rusty' color..?
.
ps. a guy who has run GCMS on various things told me that yuremamine turns a methanol or solvent solution purple...

 

[tobecomeone00]

jim jam....lol

 

[nen888]

..hey, a couple more theories on dmt-n-oxide for you..

i want to preface by recalling that 10 or more year old dmt can be slightly waxy in texture, as well as orange (as Terence McKenna used to describe it)

one of the wise ancient sages of the lycaeum said recently (as to whether dmt-n-oxide was an oil)

one has seen the yellow stuff come out with a texture almost like earwax, solid but soft. I think it's related to how it crystalizes, similar to the way that DMT that has been melted in a pipe has a waxy, amorphous shape. You should be able to recrystalize it pretty easily.

One recalls that when pulling MHRB using an STB method, it was good to play the didgeridoo over the jars before putting them in the freezer, as this helped the formation of very intricate, beautiful crystals. Also, with later pulls when both white and yellow substances were coming out, using the didge made these compounds crystalize in distinct clumps from one another.

..but then, maybe 'jim-jam' could have something to do with this: [from Noman]

It's not much of a coincidence that nobody started talking about DMT N oxide until STB teks started to become popular.
Yellow oily extracts are common with STB's - especially from solutions that have sat for awhile and/or are extracted warm. The intense alkalinity of the solution breaks he bark down so far that plant material that would otherwise be insoluble in naptha is extracted. Heat has the same effect.
These plant materials carry with them some of the alkaloids - whatever they may be - that constitute jungle or dark DMT, which is usually only extractable using a wide spectrum solvent like xylene.
When alks of dark DMT and NN DMT are combined, they form a yellow/orange goo that will never solidify. Separate them with heptane and you get crystaline NN and sticky powdery dark.
I'm not saying that none of the yellow found out there is oxide, but I'm willing to bet that the majority of it is simply NN with residual plant matter in it and a smattering of jungle alks.

..the plot thickens...

 

[nen888]

..thought i should add (from the 1st quoted lycaeum sage)

I have heard rumors that when you extract Mimosa hostilis, the yellowish crystals that are pulled (as opposed to the clear-white DMT) might be DMT-N-oxide. If this is the case, then it forms slightly yellow crystals very similar in appearance to DMT. Vaporization of these yellow crystals (whatever they are) for this subject was extremely similar to clear-white DMT, with maybe a touch more visuals. It would be great if someday, someone with access to a GC-MS confirmed what some of the unknown compounds in Mimosa hostilis are.

...

 

[endlessness]

Im not sure if n-oxides show up in GC-MS, I have to research a bit more. I think TLC/paper chromatography would be way easier and mostly anybody could make this test themselves, see if there are n-oxides present. Ill be soon posting TLC Rfs for different substances. BTW nen, I remember you mentioned some visualizing reagent you thought was better than xanthydrol, am I correct? Which one was it?