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4-AcO-DMT/4-HO-MET Fumarate water solubility

Here&Now

Esteemed member
Are there any methods for determining a chemical's solubility in water based on details about its chemical structure? Or is the only way to know from experimentation in attempting to mix it with water?

I'm specifically curious about 4-AcO-DMT fumarate and 4-HO-MET fumarate.
 
I think you mean the saturation point of said chemicals, based on the structure and polarity you could predict chemicals to be soluble. How much exactly would then only be determined experimentally.

Also don’t forget temperature plays a role here too.
 
That makes sense, thanks. Would you be able to give a quick description of how one could make that prediction based on structure and polarity? I remember learning about it a long time ago, but I've completely forgotten.
 
I’m not sure for these compounds you mentioned, but in general you could say that for polarity alike dissolves alike. And for simple metallic salts you can do the calculations based on a chart. So in your question the fumarate would make it polar so it wil dissolve in water how much however, your guess is as good as mine.

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This type of question has been a major driving factor in the development of machine learning systems. Being able to predict physicochemical properties of a novel substance, or the reverse - designing new compounds with specific, desired properties - would be very valuable indeed.

The two fumarates that you mention are, as @Varallo says, likely to be reasonably to highly soluble in water.
 
That's really interesting about the potential application of ML to help with those types of predictions. Who knows where advancements like that could eventually take us. Very exciting stuff.
 
Those are indeed quite soluble in water (did this back in the days), though remember that some subtances are not that stable in a liquid, 4-HO-MET especially has a way of degrading relatively fast in a solution of water or water/ethanol.

Then again, my 5-MeO-MiPT that I keep in 96% ethanol (the other 4% water) seems to be staying stable for years at room temperature? 🤔

Also the freebase or salt-form of a substance might change their stability in a solution.


Kind regards,

The Traveler
 
Those are indeed quite soluble in water (did this back in the days), though remember that some subtances are not that stable in a liquid, 4-HO-MET especially has a way of degrading relatively fast in a solution of water or water/ethanol.

Then again, my 5-MeO-MiPT that I keep in 96% ethanol (the other 4% water) seems to be staying stable for years at room temperature? 🤔

Also the freebase or salt-form of a substance might change their stability in a solution.


Kind regards,

The Traveler
The bare hydroxy group of the 4-OH-T derivatives, along with its position on the ring system, makes them particularly susceptible to oxidation. Oxidation equates to loss of electrons (therefore not specifically any kind of interaction with oxygen - just there happens to be a lot of free oxygen hanging around on our planet) so it follows that negatively charged or neutral species will give up their electrons more readily than a positively charged species, such as the protonated form of the tryptamine. This makes for one reason why the salts are more stable than the freebase forms of tryptamines.

This is also why alkaline solutions accelerate oxidation of 4-OH-tryptamines - the OH group is phenolic and therefore weakly acidic. As the pH increases, it becomes more likely that the OH group gives up a proton, leaving the remainder of the molecule as an anion (-ve ion), which will more readily give up its electron(s).

This is organic chemistry though, so there are exceptions and nuances largely beyond the scope of this post. One of those nuances is positioning of substituents, which brings us round to the question of relative stability of 5-substituted tryptamines over 4-substituted ones. Put simply, the way the electrons bounce around the ring system simply makes the 5-substituted versions the more stable ones. We can specifically compare bufotenine and psilocin to see this. [rummages through notes] I can add some diagrams later if anyone's interested 😁
 
I'm so glad you guys went into the "stability in solution" aspect of 4-subbed tryptamines, because that was going to be my next question. There's plenty of examples where the solution turns black within a few days. I've never seen such a detailed explanation as the one above though. Thanks so much for that. It seems clear to me that this type should not be kept in water for an extended period of time, and perhaps not at all if its integrity is valued.
 
I'm so glad you guys went into the "stability in solution" aspect of 4-subbed tryptamines, because that was going to be my next question. There's plenty of examples where the solution turns black within a few days. I've never seen such a detailed explanation as the one above though. Thanks so much for that. It seems clear to me that this type should not be kept in water for an extended period of time, and perhaps not at all if its integrity is valued.
Yes - of course, the molecules are also individually exposed while in solution, whereas in crystalline form only the surface layer is in direct interaction with the environment. The latter is a relatively tiny proportion of the whole.

4-OH-substituted tryptamines are also likely to be sensitive to light, and solution will tend to increase exposure in this case as well. If you must keep 4-OH-tryptamines in solution, they ought to be sealed under argon in glass vials and protected from light. There was a science paper not so long ago on the bluing of psilocin. Similar mechanisms and structures will probably apply to other 4-OH-tryptamines.
 
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