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Analysis of synthetic DMT and its impurities, and analysis of re-x

endlessness

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Hello all,

At our lab, we recently received a synthetic DMT sample that was allegedly made using arclightshroom´s DMT synthesis protocol (I was not familiar with it but this was sent to us by the client)

The sample came in the form of an orange oil. When analysing via LC-MS/MS and NMR, we discovered the sample was 49% freebase DMT, with the rest being mostly a DMT dimer (two DMT molecules joined at the alpha carbon in the alkyl chain), and some traces of beta-hydroxy-DMT

Here are the molecules in question:

1730028657329.png

The pharmacology of these impurities is obviously unknown, so for harm reduction´s sake, we wanted to advise the user based on some more experiments, whether recrystallizing that sample would be enough to clean the product off the impurities to avoid health risks.

After doing a single heptane recrystallization (as per our FAQ, 1g impure product in 30ml boiling heptane heated through hot water bath, stirring, and then pipetting the solvent away from the undissolved goo, and freeze-precipitating the purified DMT), the product turned to white crystals. We did another quantitative analysis and saw the product´s purity raised from 49% to 97.2%! There was no more dimer nor b-OH-DMT detected in the sample after the recrystalization

Thought this was interesting to share :)
 
Very interesting, thanks endlessness. Based on the synthetic route can you speculate where these impurities may have come from? The dimer is quite a cool looking structure.

Had the person bio assayed the product prior to it being sent in?
 
Very interesting, thanks endlessness. Based on the synthetic route can you speculate where these impurities may have come from? The dimer is quite a cool looking structure.

Had the person bio assayed the product prior to it being sent in?
Without going into too much detail Im pretty sure its because the formaldehyde, tryptamine can react with itself, leading to the formation of a dimer. So two tryptamine molecules each react with formaldehyde before reduction, linking them together.
The other reaction is the reduction that is not complete so a hydroxymethyl group may remain on the β-position of the tryptamine ring, resulting in β-OH-DMT.

In short it is because of the balance between reactants is not “optimal” and probably its not possible to achieve an balance with no side product. For example you will need the extra formaldehyde to drive the reaction forward but at the same time it will probably cause more of the dimer to form.

Note: I’m not a chemist so I might be wrong.
Mods: this is very close to synthesis talk so feel free to remove, if so apologies in advance.
 
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Isn't the perceived wisdom round here that the oily polymers / dimers are just as active and not really considered "impurities" as such?
Though I guess they strictly are if the intent of the process is to make the monomer.
 
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