Summary of DMT-Salt experiments

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I agree, stickied it!

I forgot to ask you twenty questions - is the structure depicted in the animation the crystal structure? If so, how is that determined? I can't find any studies on the benzoate.

Are the cation and anion linked in solution too? Do they trade partners or are they monogamous once linked? Would the DMT cation still be able to rotate at the alpha and beta carbons or does the benzoate anion stabilize it in the pi-sharing position?

 

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I forgot to ask you twenty questions - is the structure depicted in the animation the crystal structure? If so, how is that determined? I can't find any studies on the benzoate.

Are the cation and anion linked in solution too? Do they trade partners or are they monogamous once linked? Would the DMT cation still be able to rotate at the alpha and beta carbons or does the benzoate anion stabilize it in the pi-sharing position?

The 3d model is mostly diagrammatical, and certainly doesn't represent the crystal unit cell in any way, shape or form. The DMT and benzoate ions are positioned to hint at their π-π interactions, and it's energetically corrected as though the ion pair were in total isolation.

In solution it would tend to be more dynamic, especially in polar protic solvents. Ion pairs might conceivably exist as a fairly stable unit in a mildly polar aprotic solvent, just at a guess, although I'd be more confident in saying the real world data for this is almost certainly lacking.

Both the degree of dissociation and the level of side-chain flexibility will be temperature-dependent, but again, precise data will be thin on the ground until the actual experiments get done.

The computing power to do anything more complicated than this simple animation is, unfortunately, not presently at my disposal.

 

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Now the solution is just simple and elegant and easy to understand from the vaporization of Freebases explained here. That is the true reason why FREEBASE of nearly all Tryptamines will evaporate just below 200 °C.

Can you elaborate on this? I read the linked post but it's not quite clicking.

I was pondering the issue yesterday and trying to visualize what's happening as the melted molecules start evaporating. For fun, I was picturing the covalent benzoate molecule shedding off the crystal lattice, like a gargoyle liberated from its stone form. Suddenly free to rotate, it started flapping its benzene wings like a butterfly and flew away.

Supposedly some vapor is getting produced, and maybe that is carrying the aerosol into the air? Like steam distilling?

Then I wondered whether atmospheric gas composition affects melting point, and apparently it can:

https://www.sciencedirect.com/science/article/abs/pii/S0378381203001808#:~:text=The%20gas%20pressure%20and%20the,16%5D%2C%20%5B17%5D.

https://www.sciencedirect.com/science/article/abs/pii/S0040603108004486#:~:text=Conclusion,2%20%3C%20C2H4.

This would only be tangentially related but maybe the presence of soluble gas molecules evaporating from the melt depresses the aerosol point?

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And we should take a second look at tartrate, maleate, succinate - supposedly they've been crystallized and characterized. I also have read about picrate, methiodide and hydrobromide crystals, although I think there are practical reasons not to pursue those.

Science paper - N,N-Dimethyltryptamine (DMT) Crystalline Products And Methods Of Making The Same

It's a patent. It's written in a way that would be a pain to copy / paste over some of the content, but it seems like a very detailed description of various DMT salts. Haven't read through it yet.

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