Combination of acid salts for FASA(+) precipitation?

[Ruffles]

Suppose you make FASA (or close enough to saturated fumaric acid acetone) and add a little bit of other acid(s) into it, like nicotinic, malic, citric, ascorbic, tannic, phosphoric and so on.

Is it possible that some specific combination of precipitating salts would increase the efficiency of freebase DMT dropping out of whatever specific NPS it is in compared with plain FASA?

Efficiency here might mean many things:

Faster crystal formation
Larger crystal formation
Less contaminant acid excess or NPS solvent into the crystals
Better yield
More stable

There are many factors. The only real way to answer would be experimentating with known amount of freebase spice into known amount of NPS in sufficient aliquots for the permutations and adding each FASA(+) combo kit and maybe measuring final weight or size of crystals or taste of crystals (melting point perhaps).

 

[SawdustAndHoney]

Yeah, you answered yourself pretty much .
It's very difficult to predict things like this. I wouldn't expect mixed organic salt systems to be of any value, as one thing that is wanted in crystal formation is regularity. With a bit of 3-proton acids, 2-proton acids and acids creating a zwitterion (like nicotinic acid - remember that the pyridine nitrogen, albeit slightly deactivated, is still basic enough to accept a proton) there would be no regularity compared to just one acid anion. The only problem with fumarates is that the solubility in acetone is absolutely abismal, apart from that I don't see any reasons to improve it?

 

[Ruffles]

there would be no regularity compared to just one acid anion.

Cannot see how it would help crystallization either, like you said, increased complexity would affect regularity of the crystal matrix, but then again, someone else might see a theoretical combination, at least to give direction to an experimentation instead of trying every combination possible. Have to look for papers on this subject.

Perhaps we could avoid thinking of a bigger crystal as a good thing, and smaller and irregular crystals that are more stable, pure or give better yields be the goals?

I don't see any reasons to improve it?

There is some room for improvement in precipitating DMT with an acid that increases bioavailability of sublingual or oral DMT, as an example. Let`s say that this specific high bioavailable DMT-acid doesn`t precipitate out of NPS like fumaricDMT does, well, perhaps fumaricDMT precipitation could fish the other out of solution if its more favorable in the matrix instead of NPS. A proper ratio between fumarictheracid in acetone could be very useful.

 

[Hailstorm]

I wish I had time for experiments with benzoic acid.

It is cheap, non-toxic, widely available, and, being a monoprotic acid, it has straighforward stoichiometry - it does not produce a mix of neutral and acidic salts (unlike fumaric, tartaric, and other dicarboxylic acids).

An interesting property of benzoic acid is that, unlike fumaric acid, it is VERY soluble in acetone and other organic solvents like xylene, heptane, etc. presumably due to the non-polar benzene ring. It means you do not need much solvent to be able to precipitate DMT benzoate.

The only gotchas I can think of are 1) whether DMT benzoate is a solid, and 2) whether DMT benzoate is sufficiently insoluble in NPS and precipitates readily without having to evaporate the solvent.

 

[Ruffles]

I wish I had time for experiments with benzoic acid.

Yes Hailstorm, benzoic acid is an interesting option, nicotine benzoic salt is today`s standard pod based nic salt vaping product. Perhaps benzoicDMT may be vaped more easily than fumaric. If it drops out of NPS like fumaric it would be lovely.

 

[downwardsfromzero]

A possible area of concern with benzoates and vaping is production of benzene through their base-catalysed thermal decarboxylation. You wouldn't want to be inhaling that of course, so it might be prudent to look into the figures on that one. If anyone has the capability to do a direct test on vaporised DMT benzoate for trace benzene content, that would be the ideal experiment.

 

[Hailstorm]

A possible area of concern with benzoates and vaping is production of benzene through

Attaching a paper that suggests that vaping with benzoic acid does, in fact, result in some benzene formation. However, the amounts are small - orders of magnitude smaller than a single cigarette.

Anyhow, I would advocate vaping DMT freebase instead of salts where possible.

 

[Ruffles]

The (very good) paper indicates that benzene formation in pod vaping (nic-salt vaping) is very low, also indicates that benzene may form from propylene glycol and glycerol, which means that all e-vaping may generate benzene. Nic salt vaping is a growing market, so we should have enough epidemiological data to corroborate cancer and benzene correlation in no time.

It reinforces that ``chronically repeated exposure`` is not a ``negligible risk``. Haven`t seen a proper definition of chronical vaper so far, how many ml per day of 50-50 VG-PG with 20 mg nic salt would define a chronical vaper? Or a freebase vaping with 6 mg? That has been numerically defined for cigarette smokers.

 

[Hailstorm]

The attached paper discusses 5-MeO-DMT, not DMT. However, the following paragraph is interesting:

The fumarate salts of structurally analogous tryptamines are commonly reported, possibly due to their ease of synthesis. DMT fumarate, for example, has been previously used in clinical studies as an intravenous injection.

Fumaric acid is, however, a known Michael acceptor and has been shown to form covalent products with amine-containing APIs under mild conditions. Given that terminal sterilization by an autoclave may be required in the future preparation of sterile solutions of the 5-MeO-DMT drug product, the potential for this known reactivity with fumaric acid eliminated it as an acceptable salt form. Succinic acid is a structurally similar dicarboxylic acid but lacks the conjugated double bond present in fumaric acid and would not exhibit similar chemical reactivity.

I am all for replacing fumaric acid with succinic acid in FASA teks, especially since the latter is 3-4 times more soluble in acetone. However, I am puzzled by how exactly a tertiary amine would become a Michael donor. It should not be able to quarternize?