The Base in Your Product

[Transform]

I would love that too. Some of my concerns are more about how water could affect crystallization, not just whether it's in the crystals.

Considering the polarity of CO2, it neighbors DMT in the non-polar solvent. Maybe NaOH isn't likely to get suspended in non-polar solvent, and that could be the problem.

Carbonic acid:
Hypothetically, say you shake instead of stir, and the alkaline water thoroughly mixes with the non-polar layer. Might the more charged molecules separate first: the Na+ and OH- ions? With some H2O lagging behind and potentially reacting with dissolved CO2? Or after separating the non-polar layer into the freezer dish, and there's water vapor in the air potentially depositing into the solvent, then reacting.

Both the Na⁺ and the OH⁻ ions will be surrounded by a "shell" of water molecules when in aqueous solution. This means there aren't specifically any naked ions in solution, rather there are watery blobs which serve to diffuse the charge on the respective ions.

CO₂ is far more likely to react with a negatively-charged aquo-hydroxide aggregation than neutral water alone, since the bicarbonate anion is significantly more stable than carbonic acid.

Polymers:
And in the scenarios where OH- might be in contact with saturated freebase DMT solutes, is that related to polymerization? If we knew, maybe a filter could catch the polymers in order to separate the monomers.

If anything, it appears to be as much the associated cations that serve to enhance pi-stacking and consequent polymerisation as any effect, like deprotonation, from the OH⁻ ions. This probably appears to contradict some stuff I've mentioned before, but the ideas are broadly complementary to each other. A DMT molecule in a pi-transfer complex with a cation species would have an increased likelihood of giving up a proton, for example, even if that likelihood, as expressed by an equilibrium constant, remains relatively low.

Miscellaneous unknowns:
If there's soap residue in my jar from the last time I washed it, those surfactant molecules could effectively envelope a micelle of polar molecules into non-polar suspension.

Good observation. Fatty residues from used kitchenware could saponify and cause problems for the home extractor, too.

 

[Sakkadelic]

Dissolved CO₂ can cause losses when using distilled water for the wash.

Does this also apply to ethanol? I am making bufochanga and initially the harmalas did not seem to dissolve in the ethnaol, then later they disappeared and I noticed a little bit of harmala fluorescence. So I am wondering if some of it got salted due to ethanol picking up CO2 from the air. I did not use any acid in the process and used a small amount of lime only, so there might not have been enough base to counter the carbonic acid.

 

[Transform]

Does this also apply to ethanol? I am making bufochanga and initially the harmalas did not seem to dissolve in the ethnaol, then later they disappeared and I noticed a little bit of harmala fluorescence. So I am wondering if some of it got salted due to ethanol picking up CO2 from the air. I did not use any acid in the process and used a small amount of lime only, so there might not have been enough base to counter the carbonic acid.

That's a good observation, although it could just be that the harmalas really only dissolve rather slowly. The dissolved CO2 hypothesis would require some rather intricate experimentation to assess its validity. Are any harmala salts more soluble in ethanol than the freebase forms? We'd likely be looking at a harmala bicarbonate in this instance, were that to be the case. I'd infer you're using azeotropic ethanol, from what you've said elsewhere.

Sonication may well speed up the dissolution of harmala freebase in ethanol, however.

 

[Sakkadelic]

That's a good observation, although it could just be that the harmalas really only dissolve rather slowly. The dissolved CO2 hypothesis would require some rather intricate experimentation to assess its validity. Are any harmala salts more soluble in ethanol than the freebase forms? We'd likely be looking at a harmala bicarbonate in this instance, were that to be the case. I'd infer you're using azeotropic ethanol, from what you've said elsewhere.

Sonication may well speed up the dissolution of harmala freebase in ethanol, however.

Yes I'm using 95% ethanol, i'm not sure if the freebase has truly dissolved or if it's no longer visible in the mix. what caught my attention is the fluorescence.

Would dissolving freebase harmalas in carbonated water give the harmala bicarbonate? If that works and it can be dried, I can maybe test for solubility in ethanol vs freebase.

 

[Transform]

Would dissolving freebase harmalas in carbonated water give the harmala bicarbonate? If that works and it can be dried, I can maybe test for solubility in ethanol vs freebase.

It might do, but it's highly probable that the bicarbonate will be insufficiently stable to crystallise, just like calcium bicarbonate is only stable in solution. Compare the stability of ammonium bicarbonate for reference - solutions thereof decompose above 36°C, and a putative harmala bicarbonate very likely will be less stable than that.