IME the stronger colored spice has a more floral smell that white does not. it smells just like the flowers of a pink-white-yellow typical midwestern USA acacai or false mimosa. they grow every 20 feet where i am and on a warm summer day the steer smells just like yellow/orange spice. not the dmt smell, much more floral sampoo/perfume smell. kind of reminds me of the smell of crystaline myhhr(sp?)

Ok at least they are known plant compounds. But this still doesn't say anything about their presence in mimosa. Second I wonder if dmt n oxide formation is enzymatic or is it degradation. In the mammal system I believe adding oxygen to nitrogens to make n oxides is enzymatically controlled which means there is an energy barrier that needs to be overcome to make the molecule that may not occur under normal conditions.

This is some very nice work presented here burnt, I want to thank whoever makes such dreams!

I wonder whether anyone has dreamed of making dmt-n-oxide (I think 69ron had proposed the hydrogen peroxide route) to use as a positive control for its detection. People have tried treating the dmt with peroxide to obtain an oil similar (?!?!?) to what is thought to be dmt-n-oxide but it has never been analysed by MS.

People also report that spice left at room temperature in the presence of oxygen turns by time to yellow. Maybe that's n-oxide and also worth analysing? And from SWIM's observations, A/B on MHRB and pulling at pH of ~12 with xylene gives a a less yellow product than STB pulls (pH well on the 13+)) with xylene. Later xylene pulls from STB also give yellower products, indicating a modification on the products (that may include some oxide forming).

Finally, I am undecided whether the formation of n-oxide is enzymatically driven in the plant or an artefact of storage (e.g. gradual oxidation), extraction process and generally donwstream processing.

spice deff does seem to age. i have some 3yo spice from a mentor and its twice as yellow as when i got it.

i have the equipment/chems to do the oxide production. i also have some zinc i think. would it by chance be easier to oxidize with KMnO4? i have 8oz of that ive never used.

Maybe yes, maybe no, who knows. Molecules can oxidise in all sorts of ways, it is hard to know without trying whether potassium permanganate will induce an N-oxidation or something else.

The problem with this whole hydrogen peroxide / zinc reduction is that all that changes is the color and form of the sample. That doesn't say much about whats in it. If you take lets say freebase crystals and dissolve them into some medium polarity solvent and then add H2O2 and then evaporate the solvent and left over peroxide of course the dmt is not going to be crystalline anymore its going to get oily. If you do a zinc reduction on this material and recrystallize it you will again get crystals. You can do oil to crystal changing without even doing the hydrogen peroxide and zinc reduction. At least SWIM notices when solvent is removed at a high speed (in rotovap for example) it always turns oily. Try it you can make reasonably white crystals get oily just by evaporating the solvent differently.

So for the above reasons I don't trust any of this h2o2 n oxide formation stuff. Plus it was rons idea and he had a habit of believing in the power of color changes as an indication of making a new molecule which is rubbish.

There is a solution to this n oxide question though.

Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography-electrospray ionization-tandem mass spectrometry. E.H. McIlhenny et al. Journal of Chromatography A 2009 pages 8960-8968.

This paper synthesized dmt n oxide and set their analytical method to find it in ayahuasca. However they don't give the recipe instead they cite this paper:

Metabolism of the hallucinogen N,N-dimethyltryptamine in rat brain homogenates. Steven A Barker et al. Biochemical pharmacology 1980.

But this paper also doesn't have the recipe (I hate when authors don't cite original article its so damn annoying) either. Instead they cite this paper:

M.S. Fish, N.M. Johnson, E.P. Lawrence, and E.C. Horning, Biochim biophys Acta. 18, 546 (1955).

So this paper has the recipe to make dmt n oxide. Unfortunately I can't find the paper because its so old and in an obscure journal. If someone could try and find that paper it would be very appreciated.

Anyway then someone can just dream up a reference of dmt n oxide for HPLC or TLC or whatever analytical method one wants to use. Then we can settle that matter once and for all.

But dmt in the presence of peroxide also changes colour very dramatically. SWIM and other SWIMs have seen that. It changes from totally colourless to deep dark red within few hours. Colour may not mean much at this point, but is a good starting point to think that something between dmt and peroxide forms something else. Given that amines are known to generally react with peroxide to form N-oxides, this is really worth investigating further.

since color cannot be assumed a reliable measure, what can we use? separate solubility? bp? freeze point of the oil?

None will really say if the n oxide is formed. We need some mass data.

Infund: Could you provide a recipe with this peroxide stuff. Or link whatever. I know there is a bunch on the site but I don't know which ones worked the best etc.

[quote=burnt]
SWIM vaguely remembers 69ron's approach; that was basically dissolving freebase dmt in IPA, then add equal volume of 3% hydrogen peroxide. Or it might have been 1/5 of the volume? SWIM does not remember the latter detail.

SWIM has made this reaction but he freehanded the process. He substituted IPA for methanol, he then added few drops of 30% hydrogen peroxide and let it sit for an hour or two. After 1-2 hours the solution went deep dark red. He added few more drops after this step (just in case, to ensure complete oxidation) and let the solution sit at room temperature overnight. He then evaporated everything to get a dark red oil.

Some other members have done it in a similar way. Maybe don't use acetone in case it forms acetone peroxide byproducts.

color is used to check oxidation stages of kmno4 and other chemicals in solution. eh? predictable changes at +4 +7 etc.

also, what prevents the h2o2 from forming aldehyde in that reaction?^^^

Well, some reactions just don't happen as predicted. They may require catalysts, certain conditions of temperature/pressure, different states of the reactants (gaseous, liquid etc). Some reactions just won't happen for the life of them no matter how neat they look on paper.

when misguidedly interested in lsh i looked into producing Acetaldehyde because i felt the rum/peppermint stuff to be ghetto. for this you simply oxidize ethanol by adding h2o2. i would assume a test to oxidize dmt in ethanol would result in dmt+dmt??+ethanol+h2o+acetyldehyde.

also what i meant about the color bit, substances like vanadium xxxx-oxide and kmno4 in solution have predictable colors based off oxidation states. i was curious if you could use the marker chemical/oxidizer's color to check for oxide state and thusly infer if dmt oxide had been produced. i have no idea if you could use these colors while also reacting the chemical. was just an idea i stumbled on surfing wiki.

then again, i am no chemist.

^^Well yes you can but you have to know that the color change is consistent and that the product is what you think it is.

Do not mix your spice with KMnO4. You will totally destroy it.

lol guys im was just using that as an example of a chemical indicator being used to make reactions observable. merk/fisher prolly sell 24 packs of test plates for oxide reduction testing all prepared, it cant be that rare a thing to test. i know kmno4 is damn near useless for anything productive(i.e. not HE unstable flash powder, sucrose smoke mix, and production of MCAT). things are never as easy as diluting chemical you already have for no reason and oxidizing another chemical you already have for a unique reason.

1. 25ml heptane placed in 500ml beaker.
2. 3280mg white/yellow spice was added to the solvent.
3. beaker was placed on ceramic heating mantel until all spice was dissolved.
4. 1min was allowed for |less soluble than dmt| contam to fall out. i.e 'oil'
5. solution was carefully poured into a 25ml grad cylinder so as not to pour over any of the heavy oil/contam
6. grad cyl was heated just hot enough to inhibit precip.
7. after 1min heater was turned off and lower/heavy oil layer removed from solution with a pipette. oil yellow not orange like the oil left from steps 4/5
8. oil dropped onto glass sheet for later use.
9. 1min passed and more oil formed in the cyl.
10. this was removed in the same manner.
11. this was done 2 more times for a total of 4 pulls.
12. oil layer still forms so i stopped.


it almost seems as tho maybe it is just a more dense liquid-->solid state of dmt in solution then dry without? every time i removed the oil the solvent at the bottom where the glass base was still warmest more formed. the whole cyl was still hot too yet none formed on the walls. under 20-60x magnification no micro drops of oil could be seen precipitating. thru this whole deal i removed about 4ml of heptane. continuously removing solvent and further concentrating a saturated solution while at a temp too high for precip to form. perhaps this is not a oil, just a higher density arrangement of heptane and dmt molecules? formed from overheating of solvent, i.e. further saturating an already saturated solvent?

once this is all dry/cool i will be left with very nice spice on the walls of the grad cyl, and the removed 4ml of 'oil' will have hardened into a 90+%dmt substance that takes up 1/50th the volume.

ill post the real results shortly.

Here is the obscure paper, the last attached paper in the post, as well as the Barker et al (1980) paper, which is the first one. So yeah indeed n-oxide is done with hydrogen peroxide.

Im attaching the other paper you mentioned in your post in case anybody wants it.