Tryptamines Tryptamine solubility

[Listening]

I recently created a solution of 4-aco-dmt in whiskey. I put ~8.3mg per 1ml of whiskey. I was able to get it to dissolve pretty easily.

I kept the solution in the refrigerator. Now I notice that there's a bunch of precipitate in there. Is the solubility at fridge temperatures really too low for this solution, or is the precipitate some impurity?

 

[arrall]

Tryptamines are quite soluble in water and especially in alcohol. That concentration is pretty standard, so my guess would be that the low temperature is inhibiting the dissolution.

Take the solution out of the fridge, mix it a bit with a spoon/your preferred mixing tool, and then close it up and leave it out for an hour before putting it back in the fridge.

 

[Listening]

Take the solution out of the fridge, mix it a bit with a spoon/your preferred mixing tool, and then close it up and leave it out for an hour before putting it back in the fridge.

Yea, but the problem is that I want to keep it in the fridge, so I assume the same thing will happen again...

One other note: The precipitate seems to be dark red in color. Would this indicate that it's actually an impurity that's precipitating?

 

[arrall]

Yea, but the problem is that I want to keep it in the fridge, so I assume the same thing will happen again...

One other note: The precipitate seems to be dark red in color. Would this indicate that it's actually an impurity that's precipitating?

I don't think it would precipitate again once you put it back into the fridge. I usually just leave the mixture out for 20-30 minutes while mixing, shake the bottle a ton, and shake it up again every time I'm about to dose.

Your fridge also could be set to a very low temperature (Unlikely but possible.) I'd check the temperature control.

One other note: The precipitate seems to be dark red in color. Would this indicate that it's actually an impurity that's precipitating?

Unlikely but possible. Is the 4-AcO from a reputable non-DNM RC vendor? If not, have you gotten it tested?

 

[Pfafffed]

I personally wouldn't dissolve 4-AcO-DMT in whiskey. 4-substituted tryptamines break down quickly in water, and whiskey contains a great deal of water.

 

[Listening]

Is the 4-AcO from a reputable non-DNM RC vendor? If not, have you gotten it tested?

I'm sure it's 4-AcO-DMT... I've had a few batches of the stuff from various vendors and they all have the same effects.

I personally wouldn't dissolve 4-AcO-DMT in whiskey. 4-substituted tryptamines break down quickly in water, and whiskey contains a great deal of water.

That's interesting, though this isn't for long-term storage: It's for a few months of microdosing. In my experience, I think the degradation (even in water) during that time is negligible: at least when refrigerated.

 

[riff_messiah]

Yea, but the problem is that I want to keep it in the fridge, so I assume the same thing will happen again...

One other note: The precipitate seems to be dark red in color. Would this indicate that it's actually an impurity that's precipitating?

Interesting. When reagent testing my current batch 4-AcO-DMT earlier this year a few of the reagents formed very thin, dark red outlines after a couple of minutes. Like not in the center of the reagent drop, or even specifically localised to spots of powder, but near the outlines of the actual reagent liquid drops. I can't remember which reagents it was (think I might have it written down in a notebook somewhere), but apart from that little anomaly the reagent results checked out, and dosing was great.

 

[simstim]

Is the solution just for convenience of measurement? How much are you using as a microdose?

AFAIK the best way to store tryptamines is dry and in a mostly air tight container (like a zip lock baggie). I keep mine in the dark too, but that's mostly so they're not laying around.

It might be better to measure your daily dose on a scale if you have one accurate enough.

I know that people refrigerate LSD in solution, but 4-ACO-DMT should be much more resistant to heat and light degradation than LSD. Perhaps the refrigeration is unnecessary?

I personally wouldn't dissolve 4-AcO-DMT in whiskey. 4-substituted tryptamines break down quickly in water, and whiskey contains a great deal of water.

That's interesting. What would cause a 4-sub to breakdown in water? What would it break down to?

Could the red precipitate be DMT freebase? It seems like I've seen pictures of red DMT freebase.

Wouldn't 4-ACO-DMT be more likely to degrade into psilocin and acetic acid if it degraded at all?

 

[Skorpio]

I know that people refrigerate LSD in solution, but 4-ACO-DMT should be much more resistant to heat and light degradation than LSD. Perhaps the refrigeration is unnecessary?


That's interesting. What would cause a 4-sub to breakdown in water? What would it break down to?

Low temperature storage of chemicals decreases the rate of any chemical reaction that could be happening. Main ones to worry about are oxidation and hydrolysis.

Oxidation is the reaction of oxygen (or a different oxidizer like bleach, but typically not a case when storing things in air) with reactive portions of a molecule. Often double bonds (like in the indole ring) and oxidize. This mainly occurs on electron rich parts of a molecule. You can reduce this by wrapping a your stash tightly and storing it in a vial with low surface area (also plastic isn't the best because it is permeable to air).

Hydrolysis is the reaction of water with parts of a molecule. At neutral pH water has characteristics of both acids and bases, and can react with the molecule as well. In 4- aco DMT it will likely first react with the acetate ester to form psilocen. This can further break down though if in contact with water for long periods of time (hence the million dollar question of how long is too long, which I don't know) This reaction rate will be much quicker than air oxidation. The water component of whisky will be enough for hydrolysis to occur. If you must store the 4 aco in a liquid, perhaps try getting your hands on dmso. This does not have the protic qualities of water (not able to act as an acid and base) and will keep air away from the compound, and permit for liquid dosing. It is relatively non toxic (ld50 higher than ethanol, and used as a carrier for pharmaceutical drugs) and a great solvent. It will make your breath kind of garlicky (because it's got some sulfur in it; people consume it as an alternative medicine because it's a sulfur source. I don't think it has any particular benefit tho). Caution should be used because it can allow things to permeate your skin (probably not well enough to transdermally dose 4 aco but it is used for a lot of transdermal drugs). You wouldn't want to let it sit on skin covered in pen ink for example because it could possibly increase your body's absorbtion of the ink.

The only drawback of low temp storage in a fridge (assumin the compound is going to be stored as a powder. If it is stored in solution this would be a non-issue,becaue it would be either in water already or in a different solvent) is that condensation could form and the drug could get wet (which allows for hydrolysis to occur). If you could store it with a dessicant pack (usually silica gel, but calcium sulfate works too, there's a type of the calcium sulfate dessicant called drierite, which changes color as it absorbs moisture, and can be redried by heating in an oven).

 

[simstim]

Well if it hydrolyzed into psilocin at least he's not really losing anything, but is this really likely to happen significantly without a strong base in the solution?

I was just reading that the hydrolysis of an ester happens in the presence of hydroxyl ions. So in the presence of a strong base (like NaOH or KOH).

I don't think water alone is strong enough to break the bonds of an ester to an appreciable extent by itself. Not unless maybe it was stored that way for a period of years, or maybe if it was stored in extreme heat. Even if it was stored for years it sounds unlikely to me that the bulk of the stored ester would be hydrolyzed.

If what you were saying is true it would be impossible to store injection solutions of ester-containing pharmaceuticals.

That would mean no injection solutions of diphenhydramine, any of the 'caine anesthetics, and who knows what else. I have seen aqueous injection solutions of diphenhydramine and local anesthetics so I know they can be stored in aqueous solution despite containing ester linkages.

 

[Skorpio]

Well if it hydrolyzed into psilocin at least he's not really losing anything, but is this really likely to happen significantly without a strong base in the solution?

I was just reading that the hydrolysis of an ester happens in the presence of hydroxyl ions. So in the presence of a strong base (like NaOH or KOH).

I don't think water alone is strong enough to break the bonds of an ester to an appreciable extent by itself. Not unless maybe it was stored that way for a period of years, or maybe if it was stored in extreme heat. Even if it was stored for years it sounds unlikely to me that the bulk of the stored ester would be hydrolyzed.

If what you were saying is true it would be impossible to store injection solutions of ester-containing pharmaceuticals.

That would mean no injection solutions of diphenhydramine, any of the 'caine anesthetics, and who knows what else. I have seen aqueous injection solutions of diphenhydramine and local anesthetics so I know they can be stored in aqueous solution despite containing ester linkages.

At a pH of seven water is composed of equal amount hydroxyl and hydronium ions. Lower and higher pH are just different ratios of the two. That is why water can perform both acid and basic hydrolysis. The rate is drastically increased at extreme pHs of course, but for something as labile as an ester, it is not an issue to hydrolize at neutral pH.

Psilocen degrades as it forms dimers through an oxidative reaction. This degeneration reaction which occurs in water is responsible for the bluing in psilocybe mushrooms.

 

[simstim]

This article says water hydrolysis is extremely slow and I'm fairly certain it is unlikely to completely hydrolyze the entire dissolved product. Especially at room temperature or colder.

hydrolysis of esters

Splitting esters into acids (or their salts) and alcohols using water, dilute acid or dilute alkali, including splitting of large esters to make soap.

www.chemguide.co.uk

Another article I read said hydrolysis in the presence of an acid is possible but it is also completely reversible and will not run to completion. Also, it is necessary to reflux the solution.

If you're intention is to make psilocin from 4-ACO-DMT then you would want it in a solution containing a base (probably NaOH) and you would reflux it. This one will run to completion leaving you with a product of psilocin and sodium acetate in aqueous solution.

15.9: Hydrolysis of Esters

Hydrolysis is a most important reaction of esters. Acidic hydrolysis of an ester gives a carboxylic acid and an alcohol. Basic hydrolysis of an ester gives a carboxylate salt and an alcohol.

chem.libretexts.org

I really don't see how this could happen to a significant degree in the refrigerator and without the presence of a base.

 

[Listening]

Thanks for the informative responses all. More details:

• There is very little of the precipitate compared to the amount of liquid
• It is cloudy / wispy / fine
• If I shake the mixture, it disappears, but I have a feeling it's not getting dissolved, but just suspended evenly... Next day I see it again.

When reagent testing my current batch 4-AcO-DMT earlier this year a few of the reagents formed very thin, dark red outlines after a couple of minutes. Like not in the center of the reagent drop, or even specifically localised to spots of powder, but near the outlines of the actual reagent liquid drops.

I've seen that before when reagent-testing other chems. No idea what, if anything, it means.

Is the solution just for convenience of measurement? How much are you using as a microdose? ... It might be better to measure your daily dose on a scale if you have one accurate enough.

A micro-mini dose will be something like 2mg-3mg. My scale is not accurate enough for that. Also it's just more convenient/easy/fast/accurate to liquid dose. (For normal trips I use a scale for a single dose, but for micro-mini doses, it's not practical.)

AFAIK the best way to store tryptamines is dry and in a mostly air tight container (like a zip lock baggie). I keep mine in the dark too, but that's mostly so they're not laying around.

The only drawback of low temp storage in a fridge is that condensation ...

FWIW, for long-term storage, I store all my chemicals in the freezer in mason jars filled with silica crystals. When I take them out of the freezer I wait ~20 minutes or more before opening the jar (to avoid condensation). As far as I can tell, no degradation in any of them over ~15 years so far. I'm confident that they'll last my whole life this way.

 

[simstim]

Thanks for the informative responses all. More details:

• There is very little of the precipitate compared to the amount of liquid
• It is cloudy / wispy / fine
• If I shake the mixture, it disappears, but I have a feeling it's not getting dissolved, but just suspended evenly... Next day I see it again.

Is this solution being stored in a sealed container?

Since it's not going back into solution, and going by your description, I wonder if some contaminate didn't fall into it. Or maybe something is growing in it? I don't know what kind of refrigerator mold can grow in whiskey, though.

I can't imagine that 4-ACO-DMT would precipitate out and float on the top unless it was somehow basified and that's the freebase floating around.

If it was precipitated psilocetin fumarate then it should form crystals that would then sink to the bottom of the solution. It shouldn't ever be floating on the top.

Perhaps some sort of residue that was already in the container before you added the solution?

 

[Listening]

Is this solution being stored in a sealed container?

Yes.

Or maybe something is growing in it?

Well, funny you should suggest this: When I first spotted it, I freaked out and dumped the solution, sterilized everything and made a new one from scratch... The next day I saw the same thing. Also, it doesn't get worse over time, so I don't think anything is growing in there.

 

[Skorpio]

FWIW, for long-term storage, I store all my chemicals in the freezer in mason jars filled with silica crystals. When I take them out of the freezer I wait ~20 minutes or more before opening the jar (to avoid condensation). As far as I can tell, no degradation in any of them over ~15 years so far. I'm confident that they'll last my whole life this way.

This is how chemicals are treated in lab settings, and it really is the best way to store them.

 

[Skorpio]

T

presence of an acid is possible but it is also completely reversible and will not run to completion. Also, it is necessary to reflux the solution

That's just to get a complete reaction. Enough time any you will reach an equilibrium of h2o and hydrolized ester. Also I'm always gonna lean conservative when it comes to long term storage of potentially rare things.