DMT N-Oxide to Freebase DMT

[Mindlusion]

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 :? :surprised

.

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.

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....

 

[Brennendes Wasser]

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

Again just mostly Spice and still brown :?

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 :|

 

[Mindlusion]

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

Again just mostly Spice and still brown :?

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 :|

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.

 

[Brennendes Wasser]

Yeye I understood this, it was just my thoughts how that compound could be isolated as recrystallization seemingly produces white spice again, leaving that other stuff behind which coudl be fetched up again.

Maybe gonna have some chance for this the next weeks, gonna have to see.

 

[benzyme]

Its likely not a single compound but many of higher molecular weight, dimers polymers, that kind of mess.

this is actually quite plausible, and has been cited in literature, polymers formed about the terminal amines.
I just wonder if that occurs during ionization (i.e ESI), or high temperatures.

 

[Hupecat]

i fiddelt around with zinc and leftover oxides from previous extracts.
it really works like a charm

it was extractedf from the mini a/b with heptane then.

 

[benzyme]

I'm wondering if the zinc is even necessary. A/B will cleave polymers, and resolve residues; hexane/heptane wash will consistently result in white/off-white crystals, when the solubility equilibrium is exceeded. Those crystals will gradually turn yellow/orange, with exposure to air at ambient temp, over time.