Solubility of DMT in different solutes.

[Hank Scorpio]

Long story short, I'm trying to roughly calculate some expected yields, but for that, I need some measures of solubility in different media. I'd like the solubility ratios of DMT in water vs. naptha at room temperature or above, and the solubility of DMT salt (that one would get in an mini A/B cleanup with acetic acid/vinegar) in water/acetic acid vs. naptha.

Brennendes Wasser already made a really helpful experiment on the solubility in naptha in the freezer: Solubility of DMT in Freezer - Advanced/Enhanced chemistry - Welcome to the DMT-Nexus

Now, I can find various computed values for the solubility ratio of DMT/Water in Octanol online:

Compound: N,N-DIMETHYLTRYPTAMINE

Molecule Type: Small molecule, Molecular Formula: C12H16N2, Molecular Weight: 188.27, Synonyms: N,n-dimethyltryptamine

www.ebi.ac.uk

These are all calculated numerically, but I read a paper saying that the calculated solubilities correlate with the real solubilities with a coefficient of like 0.8-0.9, which is good enough for my back-of-the-envelope calculations. Now, what I'm not sure of is, if the solubility in octanol is a good enough proxy for the solubility in hex/heptane/naptha.

What I can't find at all, is any estimate of the solubility of the salt. Does anyone know any source for this? I would be happy even to have a ballpark figure. Are we talking 10, 100, or 1000 times more soluble?

TL;DR
Is the solubility ratio in octanol comparable to the solubility ratio in naptha?
Whats the solublity of DMT in acetic acid vs naptha?

Thanks in advance.

 

[downwardsfromzero]

Just a heads up - 'solute' is the stuff that gets dissolved in a solvent, so your title is a little confus(ed/ing).

At a back-of-the-envelope level the solubility ratio of DMT acetate in water vs. naphtha is close enough to 1 not to have to worry about it. If your NPS were DCM, that would be a different matter. Overall, it's still a good question, though. DMT and acetic acid aren't that strong a base or acid, respectively. Aqueous acetic acid succeeds in pulling DMT out of naphtha pretty well because naphtha is a fairly poor solvent for DMT. It turns out this is something of an advantage if your goal is to obtain crystals of freebase DMT.

 

[Elrik]

Your yields will be more greatly effected by other factors as to make these factors non-relevant, in most examples.
For your ballpark figures 100% freebased DMT would be 10 000 times more soluble in toluene than water and DMT acetate would be 10 000 times more soluble in water than toluene.
There are cases where the water might hold on to a little, or the solvent might become saturated [as mentioned above with some naphthas, heptane would be worse].
I've made small batches of DMT base with a carbonate+heat based saline/isopropanol partition method in which the saturated saline picks up like 10% alcohol. Even that worked.

In extractions you are rarely extracting from ideal solutions, there are various things the alkaloid can 'get stuck to' and that will effect yield or the need for multiple pulls more.

Mescaline extraction takes more work because mescaline actually is soluble in water and is simply more soluble in xylene. So with mescaline you pull and pull and pull until the last pull was barely worth it, at which point you accept the remaining loss. That sounds like the scenario you are worried about, its only a mescaline thing. Or caffeine.
Ironically, two days ago I finally titrated a 'bonus' xylene pull I made from my last DMT extraction. I got a couple grams from the first 3 pulls and that last pull just gave me 150 mg :lol: If it were a mescaline extraction pull #5 would still be worth doing.

If you're worried that a solvent isn't capable of dissolving enough DMT then extract your based soup with xylene, salt the DMT out of the xylene, and process it further in a clear solution with a solvent that it will freeze crystallize from, like heptane.
Some people hate the extra work, while others love playing in their mini-lab. That value judgement is yours to make

Addendum: if your worried that solvents will cost lots of money, they can be recycled at home. All of our favorite solvents form azeotropes with water. That means, even if the literature says a solvent boils high you can make it distill below the boiling point of water. For instance, xylene 'boils at 139°C' but if you add some water to it the mixture boils at 94°. This means with an investment in a glass distillation kit including a boiling flask, a water jacketed condenser, two adapters, a receiving flask, a thermometer or two, some buckets and tubing for gravity-feed cooling, and optionally a fractionating column at least 10 cm long you can recycle solvents in a mineral oil bath on an electric stove. There is barely any odor when I distill xylene-water azeotrope.
For the dedicated extractor.

I'll never run out of xylene, toluene, naphtha, or isoöctane because I recycle them and with my 20 cm fractionating column I can reclaim ethanol used in ethanol-water recrystallizations.

 

[Hank Scorpio]

Thanks for the answers guys!

Yes, I mixed up solvent and solute. Thanks for the tip.

downwardsfromzero, I'm a bit confused by your answer. You say the solubility ratio is close enough to 1 to not worry about. A ratio of 1 would be really bad, right? That implies that the DMT is equally soluble in water and naptha, which would leave a lot behind. You mean a ratio of infinity or 0, right?

Elrik, I'm not sure that a ratio of 10,000 is quite right. From the solubility ratios I got online (for octanol/water), the ratio was about 100.

If the solubility ratio of DMT acetate in water vs naptha is also at least 100, then I can get some decent yields, according to my numbers.

 

[Elrik]

The octanol/water partition coefficient test is done because octanol is low range in polarity but is polar. The numbers spread out more evenly when testing different solutes of varying polarities so it's more useful in getting an idea of somethings polarity in relation to solvation properties. No one actually uses octanol as an extraction solvent.
Even the more polar of the solvents we use for pulling are far less polar than octanol. Octanol is closer to alcohol in solvent properties [its actually soluble in water to the extent of 0.05%], while xylene and especially things like heptane are more like candle wax.
In basic water DMT is essentially insoluble, just like DMT acetate is essentially insoluble in xylene or naphtha. It makes DMT one of the easiest hallucinogenic alkaloids to work with, if not the easiest.

The other things in a crude extraction can trap freebase DMT in the aqueous phase by multiple methods, like bark powder holding on to DMT globs like a sponge with grease on it and the tannins in barks are acids and so can pull DMT a little in the direction of the water if there isn't enough strong base. The latter is why you cant extract bark with sodium carbonate but you can freebase a clear solution of a DMT salt with sodium carbonate, carbonate just cant fight against tannin well. Neither can too little lye.

 

[downwardsfromzero]

100% = 1

Apologies for using undefined terminology, and sloppily at that. Late night posting causes cognitive flatulence.


Octanol might actually be a pretty good solvent for DMT

 

[Elrik]

Octanol would be more difficult to recycle than solvents we use, would contaminate any salt product due to its water solubility, couldn't be reasonably evaporated from a freebase product, and would be expensive.
I'd love to have a litre of it to play with, but not for DMT extraction.

 

[downwardsfromzero]

Long chain fatty alcohols have cropped up as "eco-friendly" BBQ lighting fluid at times.

 

[Hank Scorpio]

Just to be clear, I'm not at all interested in using octanol as a solvent. I was interested in using the solubility ratio as a proxy for the solubility ratio of naptha in my calculations.

I've found a good experiment done by samvidbuho: Solubility Studies 2: The Thermodynamics of DMT Crystallization - Freebase Solubility Curve - Advanced/Enhanced chemistry - Welcome to the DMT-Nexus

which suggests that the solubility of DMT in n-heptane is about 5mg/g at room temperature. Using the density of heptane from wikipedia gives a solubility of about 3.4mg/ml in heptane at room temperature.

Meanwhile, I have an estimated value of 1.69mg/ml for the solubility in water at room temp from Dimethyltryptamine: Uses, Interactions, Mechanism of Action | DrugBank Online

If this estimate is correct, then the solubility ratio at room temperature is really only about 2. Which is disappointingly low. To get a solubility ratio of close to 10, or 100 or whatever, either this estimate needs to be off by a couple orders of magnitude, or I've messed up my calculations badly.

The solubility in n-heptane estimate from samvidbuho seems to roughly gel with brennendes wasser's estimate of solubility in the freezer, with the solubility of DMT in naptha being on the order of single-digit milligrams per milliletre.

What are your thoughts? Do we have a better estimate of the solubility in water?

 

[Elrik]

What you have to understand is that the relative insolubility of DMT in heptane and pure alkane naphtha ['odorless' or hydrotreated naphtha] are exactly why people use those solvents. The solubility is increased with heat so people extract warm or hot and then put the solvent in the freezer to get DMT crystals, leaving only a little dissolved in the solvent.
If you want a solvent that will dissolve lots of DMT you can use something like toluene or xylene. Then you just have the issue of isolating the DMT base from that solvent.

DMT base lasts me forever so my personal method is to pull into xylene, salt it into DMT bifumarate and collect the crystals from the evaporated water layer, then when I want a gram of DMT I'll dissolve some bifumarate in a minimum of water, base with sodium carbonate, add isopropyl alcohol, saturate it with salt, isolate the alcohol and do a second alcohol pull before combining them and evaporating to get thick DMT goo. I think my method is unique :lol:

If I wanted crystals I'd extract into xylene as I normally do, salt into water with the cheapest acid handy, isolate the water layer, concentrate it if the acid was non-volatile, base it and extract warm into pulls of something like heptane or isoöctane, and freeze crystallize from there. The little bit that remained in the heptane could be salted out and saved once I was done making crystal DMT.