I read here Acetates... that DMT can be smoked/vaporised as acetate. I'm not too good in chemistry, and I wonder why this DMT salt can be vapourised while it is kindda a rule that salts will have a higher, typically above decomposition temperature, melting point than freebases.
I thought it could have to do with acetic acid's low boiling point but then HCl has an even lower boiling point. Is it related to pH and the strength with which the alkaloid and the acid are attracted to each other? Or is that sort of extremely technical chemical stuff?

Thanks

Vaporization occurs more easily with DMT acetate - and, it appears, the benzoate - in part because of the combination of weak acid and weak base. The relative volatility (ease of vaporization) of the free acids certainly plays a part too. It' s highly likely that the phosphate and the sulfate of DMT would not vaporize at all easily. HCl is a stronger acid - but the actual difficulty with DMT HCl is its extreme hygroscopicity to the point of deliquescence.

So it is due to the pH, sort of, and the "strength with which the alkaloid and the acid are attracted to each other" has the technical term "intermolecular forces". The relative charge distribution is one factor that relates to both pH and intermolecular forces; thereafter it does become more technically involved, so I'll happily leave it at that!

Thanks for your thorough reply. This is helpful while I improve at chemistry

I think based on some experiments I have the feeling something else might (also) play a role.

Actually what you do when smoking your Alkaloids is not boiling them like you would boil water when crossing the 100 °C mark. So you are right: A salt would just evaporate at waaay too high temperatures.

But funny enough also the Alkaloids themself would take way too high temperatures, which would actually destroy them first. A great explanation can be read here. The OP gives a really detailed insight into what actually happens. If you would really boil the Alkaloid then the vapor would be INVISIBLE! I have really boiled DMT at its boiling point (allthough at reduced pressure, otherwise it just gets destroyed) and it is indeed completely invisible. You only see it as a clear condensate, where the temperature just is low enough to start condensation. Otherwise: invisible.

Instead what happens is that small droplets of the Alkaloid are formed, an Aerosol. These droplets are really small and get carried into air easily, resulting in you inhaling very fine liquid spheres, that basically have the same effect as you would inhale a gas. Now also only this process is creating something that can be seen by eye: the vapor clouds that we all can observe while inhaling. Now when inhaling this aerosol, the droplets are micrometer-sized and therefore bigger than the actual wavelength of light, so they can cause diffractions. That again makes the droplets visible macroscopically as the vapor that we all know and love ( ). But with *real DMT-gas* it's impossible to cause diffraction of light, because the single molecule is way smaller than the actual wavelength of light itself. Therefore aerosol droplets can be seen, *real gas* cannot.

Now that was all just regarding Alkaloids, which (without any further mentioning) would primarily mean a Freebase substance. But in my opinion it looks like exactly the same is happening with salt forms of DMT. They also seem to be able producing these aerosol droplets just after they melt. And because of this, DMT Acetate (and quite some others) can be smoked at below 200 °C just like Freebase DMT, even though their true boiling point is waaaayyy too high.



I wrote somewhere just some empiric finds, not sure if they are valid, but seem consistent with all the experiments.

Some rules of thumb:

- Aerosol formation starting around > 170 °C for all "compatible" Alkaloids or salts, so these can be smoked at this temperature regardless of their true boiling point (which might vary a lot)

- Adding hydroxy groups is slowing down evaporation strongly

For salts only:

- strong mineral acids will never form aerosols and just cause pyrolysis
- carbonic acids with low molecular weight and intermolecular forces are most desirable (low count of polar groups)
- monovalent acids (only 1x R-COOH) that fulfill above requirements will produce a salt with melting point 120 - 160 °C, which is faster starting aerosol formation, thus desirable.
- multivalent acids (2x or more R-COOH) will produce salts with melting points of 180+ °C and thus start aerosol formation also later, thus increasing chance of pyrolysis.

Acetic-Acid-Salts evaporate really well, but it seems most Alkaloid combos result in goo. Benzoic Acid seems to be the best option. Succinic Acid and Fumaric Acid dont evaporate so well and need a little higher temperatures ... Oxalic was not tried, but probably same case.

So given these observations it seems when using a "compatible" acid you will be able to proceed your salt just like a freebase. It's only important to make sure that there is no excess of acid hiding in that salt, which will cause a strong irritation upon inhaling.

Still if your alkaloid can be crystallized in its Freebase form - like DMT - I see no benefit of doing that hassle But maybe some applications will be found in future.

Just a footnote about oxalic acid:

I seem to recall it can be purified via sublimation [e.g., see here as practical application of ox.a. sublimation], which may be a good sign. On the other hand, one of its modes of decomposition is by forming carbon monoxide, which is somewhat less desirable. And considering there's a synthesis of formic acid which involves heating oxalic acid with glyerol, we ought to consider its role as a hydrogen acceptor. Whether this would lead to polymerisation or the formation of a cyclised dehydrogenation product like 2-methyltetrahydro-β-carboline I can't yet say.

So, the thermolysis of DMT oxalate would at least be an interesting experiment to try out, especially for those wiih access to analytical machinery. Then again, any Nexian has access to analytical services if they're willing to discuss arrangements with certain senior members, or to look online for alternatives.

And thanks again for the great explanation, Brennendes Wasser.

So the explanation if from AbsolutelyPureDMT, so credit goes to him. I was then simply sure the same must be happening with the salts (at least the ones that "work". And now this is also a great explanation for the results of my Salt-Vaporization-Experiments, which weirdly gave all signs that the vapor contains DMT+H(+) and Benzoate(-) instead of pure Freebase + Acid or any other combination. That sounded completely non-intuitive, but makes perfect sense if the vapor is just an aerosol again.

This is actually also the reason why a Salt-Form vaporized does not exhibit a strong "Freebase-burn" in your mouth - in my opinion

Regarding Oxalic Acid, it could be tried of course, but I already have some data for an Alkaloid Combo with Fumaric Acid and it shows that evaporation is way less efficient than with Benzoic Acid. I checked before on a hotplate and it seemed to at least vaporize. But of course the total efficiency can only be seen in TGA. So while on hotplate the Alkaloid-Fumarate gave off nice fumes, it only vaporized down to ~ 50 % seen in TGA. Therefore even if many salts seem to give off strong vapors by eye, the *Quality of vaporization* can still be very different

And considering the original question:

It should also be noted that even if aiming at storing your Alkaloids as Acetates, it might not be favorable for long-term stability. In theory the acid will block the Nitrogen from reacting as a base, and this would be probably the primal decomposition pathway at ambient conditions.

But Acetic Acid will form a goo, and goo's are in general less stable than a solid (crystallized) substance. Reason is that most chemical reactions of solids require some mobility of the molecules. That is normally achieved by using a solvent, which is serving that purpose in order to make the educts react with each other. In a solid crystal grid the mobility of molecules is near 0 compared to a dissolved state (allthough non-directed vibrations within the crystal grid are still on a high level). This already slows down any possible reactions by a lot. If handling a goo, then this will cause a fast decay of your Alkaloid, probably even if it is in a salt state. Thats why it is always desirable to opt for a crystallized plant extract, rather than keeping a goo at the end of any nature-product-chemistry adventure. If not possible, diluting in something sterile is still an option, but still less viable than having a solid crystal.

Closest you could get with Acetates would be dilute it in water and freezing it at -20 °C. But other than this storing Alkaloids as a goo is probably never optimal, not even when keeping them as a salt. Instead using acids which will enable crystallization is much better for long-term storage (but therefore Freebase is just fine)