I think Brennendes Wasser did some analysis on this topic but I am quite not sure.
In my experience, DMT in freebase form is stable sufficiently enough to don't go through
adventurous procedures for little quantities.
After one year and more, airtight conserved freebase seemed to stay powerful like a pregnant Tigress.

I don't see why conservate it like this?

donfolio is right,
I observed a freebase crytal for a couble of mounth under the microsocobe.
Even it was permanently exposed to indirect sunlight and fresh air, the molecule just degradet a little bit and maybe oxidated.
It still hit me like a brick after 4 month.

If you put it in a black class fiole in your fidge its not changing at all.

I think the fear of FB DMT degrading over time is overblown. I store in freebase form, room temperature, in a jar with a desiccant taped to the bottom of the lid, and I have noticed zero loss of potency after three years.

Syragote, heptane itself cannot degrade DMT - it is chemically inert for all practical purposes.

What can react with DMT molecules is oxygen, carbon dioxide and other chemicals (if I am not mistaken, 100g heptane can dissolve up to 0.035g molecular oxygen or 0.619g carbon dioxide). Much more is present in the atmosphere - albeit more slowly, atmospheric gases also react with DMT at the surface of the solvent.

Molecular oxygen does not react with DMT directly. However, when the two oxygen atoms split apart, each will carry an unpaired electron. Such free radicals can react with the nitrogen in DMT to form DMT N-oxide, a yellow oil.

Carbon dioxide reacts with that same nitrogen to form carbamate esters. That reaction (unless followed by further transformations) is luckily reversible and even modest heating will split CO2 off. However, unlike freebase amines, carbamates have different solubility properties, which may lead to some DMT loss in handling, purification, etc.

Converting DMT to a salt (hydrochloride, fumarate, benzoate) binds the lone pair on the nitrogen to a proton from the acid, making the nitrogen far less reactive and more stable in air.

Dissolving any chemical compound drastically increases its surface area - the molecules, instead of sticking together like male penguins, disperse and become exposed to whatever reactants are there. This is one of the reasons chemists use solvents - to dramatically accelerate reactions through large contact surface areas. Unfortunately, it also means that whatever can degrade DMT can have an easier time doing so.

If you want to experiment with storing DMT in a solvent, the following should work (but is probably an overkill):

1) Degas the solvent (bubble argon through it, pull a vacuum, etc.) before dissolving DMT in it.
2) Cover the DMT solution with some argon, or hang some oxygen absorbers in the headspace of the container.
3) Close the container and keep it airtight.
4) Shield the container from light (amber glass, aluminum foil, ...) to reduce formation of free radicals.
5) Store the container in a good medical freezer to slow down whatever reactions may still occur.
6) Warm it up before opening to minimize water vapor condensation.

Two things to give particular consideration are dissolved water and traces of base contamination. More on this in a moment.

Experimentally, it has proven difficult to generate DMT-N-oxide without the use of hydrogen peroxide or a peroxy acid. The current thinking, based on limited analytical evidence, is that DMT, in the presence of moisture, undergoes a base-catalysed oligomerisation at the indole ring. In my view, oxygen molecules are likely to act as an electron acceptor in this mechanism. Molecular oxygen exists as a diradical in its ground (lowest energy) state, with two unpaired electrons. Thus it is not necessary for the oxygen molecule to be split apart in order for it to react with pretty much any source of vaguely spare electrons. This property is behind the peroxide formation which occurs readily with a numerous types organic molecules - ranging from polyunsaturated fatty acids, to (certain) ethers, to alkenes. The oxidation of DMT, and indeed many other oxidisable substances, need not involve the addition of one or more oxygen atoms. Loss of one or more electrons is also a form of oxidation.

Amine auto-carbamates only form with primary and secondary amines. DMT is a tertiary amine and thus won't react with CO2 in this way. This is exploited in the CO2 method for separating NMT from DMT.
The other thing that happens with salt formation is that it eliminates the great majority of the basicity of the amine. This means that the freebase DMT can't act as its own catalyst in the above-mentioned base-catalysed oligomerisation.


All good stuff. The degassing should remove the majority of water contamination but if this is perceived as being critical then the solvent can be dried with a compatible drying agent or a chemical drying method, the nature of which is dependent on the solvent being used.

After removing a storage container from cold storage, there is the problem of condensation which forms on the outside of the cold container. It is therefore prudent to package the storage container in a secondary container which also contains at least some desiccant if not an inert atmosphere. The whole package can then be allowed to warm to room temperature without condensation forming on the outside of the primary storage container, which would otherwise risk compromising the pains taken to ensure the integrity of the sample. [Sorry, too much coffee ]

Yes, thanks, I am aware of this possibility (and benzyme has the same opinion, AFAIK). The two other possibilities I have heard about are N-oxide formation and crystalline polymorphism.

Recently, a MS/MS analysis of partially degraded DMT has indicated N-oxide presence. Attaching the spectrum (not mine).

Another, indirect evidence of N-oxide mechanism is the stability of MIPT in air, as noticed by Shulgin and later confirmed by another forum member. MIPT is more sterically hindered than DMT, which should impact N-oxide formation more than basicity. I know that benzyme has recently made DIPT - it would be good to know if DIPT, which is even more hindered, is also stable in air.

(duplicate post)

I was referring to page 699 of the attached paper (see 2.2.1), which states "while ground state molecular oxygen is generally unreactive, photosensitization in solutions can generate singlet oxygen, which reacts readily with Trp to form multiple oxidation products".

I was wrong about this one - there are indeed no stable carbamates to deal with. Maybe I should take a break from primary amines )). However, DMT should still react with CO2 to form DMT bicarbonate (see (2) in the attached paper) if water is not excluded.

Yes, and the paragraph continues, "It is commonly stated that the 3-hydroperoxytryptophan (38) is the first formed product via the Schenck ene reaction, which can then re­arrange to the dioxetane 39, however the formation of the dioxetane directly from [2 + 2] cycloaddition with singlet oxygen has not been disproven."

The oxygen reacts as a diatomic moeity. ("Singlet oxygen" refers to the electronic state of the molecule rather than the number of atoms that are reacting.) Of course, when the N-oxide is formed only one oxygen atom ends up attached to the amine nitrogen so, yes, splitting up of the oxygen molecule must occur at some point during N-oxide formation - but that situation is distinct from peroxidation reactions at the indole nucleus.

This carbonate formation has been noted with mescaline as well. According to Valentine-Smith, the freebase absorbs carbon dioxide and moisture from the atmosphere to form the carbonate although I have wondered whether it is the auto-carbamate that (also) forms in that case, mescaline of course being a primary amine. This is something I will check out.

Thanks, very interesting.


I imagine that, with primary amines, both reactions (carbamate formation and protonation by carbonic acid) are taking place, and both are reversible. The attached paper discusses the rates in aqueous solutions; in (relatively) non-aqueous ones I'd assume carbamate formation would dominate the equilibrium?

Thanks for the interesting discussion, I appreciate the literature references you've been digging out.
Yes, the relative absence of water does seem to imply that that would be the case.

Ive seen evedence that DMT can be stored for a very long time in Ethanol..concidering its polar and non polar...

Ive even samples the stored molecule..and it maintains plenty of effect!... even after 14 months in storage in dark amber bottle in cool invirment...