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Precipitation of DMT out of chloroform

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Adivino

Adivino

Rising Star
Chloroform was left to stand at room temperature in a large evaporation plate (no fan was used). During the evaporation, a thin layer of white crystals formed on the surface of the solvent. However, after the complete evaporation of the chloroform (i.e. no smell present), an oily orange/brown residue was obtained.

Is this the infamous N-oxide of DMT? If so, it appears that simple evaporation is not the correct way of removing the solvent. Some authors claim to do this, but they are apparently using a rotavap at reduced pressure.

Is it possible, then, to force the precipitation of DMT out of chloroform, just like it's done from petroleum ether? Freezing (-20°C) the chloroform for 2h formed no crystals.
 
DMT will most likely be too soluble in chloroform even at freeze temperatures, hence why no crystals formed.

I would avoid using halogenated solvents with DMT, due to possible reaction. DMT has been documented to react with DCM after a few hours, im not sure if it would with chloroform, maybe not, but I would avoid it (also its quite toxic/potentially carcinogenic, im sure you know, so please work with good ventilation).

Its hard to say what the white crystals were. Why are you usign chloroform at all? Why not any other of the solvents that work so well?
 
honestly, no solvent works better than chloroform or dcm at extracting DMT, and the side-reaction requires certain conditions to occur (basic conditions with extended exposure to haloforms). a quick extraction with dcm or chloroform probably isn't enough time for these reactions to occur.
dmt is most soluble in these solvents than all others proposed, and only a single extraction is done with room temp chloroform or dcm, as opposed to three or more with heated naphtha.I usually use 1/10th the volume of dcm to basic phase.

evap, then recrystallize in pet ether or heptane.
 
Benzyme, I actually did what you state, and I'm waiting for results.

endlessness, chloroform is a great solvent to use with a dropping funnel (pet ether, d-limonene and others having SG < 1), and very efficient to extract alkaloids. I was also under the impression that evaporation was reasonable, but it appears that not.

Benzyme II, when you say "evap and recrystallize from pet ether", how is the evaporation done in practice? Does it not turn orange like in my experience?
 
Yeah in the publication regarding DCM reaction with DMT, they left it for many hours (or days?) to stand... I dont think it was in basic conditions though, just the alkaloid dissolved in the solvent that was left to stand, already separated from the basic acqueous solution, but I would have to dig it up and read again to be sure.

In any case I guess I would be cautious since we have no idea the safety profile of N-chloromethyl-DMT chloride and we dont really know exactly how fast this will occur in the OP's conditions of extraction.... So if you use DCM/chloroform, try to remove the alkaloids from it as quick as possible, otherwise better not use it.

By the way, maybe salting like with FASA/FASI would work with chloroform?
 
Benzyme, do you mean adding anh. acetone saturated with fumaric acid to the chloroform to salt out the fumarate? This sounds interesting.

Also, I asked you something above in an edit, but you may not have read it: when you say "evap and recrystallize from pet ether", how is the evaporation actually done in practice? Does it not turn orange like in my experience?
 
That would be the idea of FASA, adivino... Ive done it with different solvents but never with chloroform.. With limonene, infundibulum mentioned how it weirdly didnt work because FASA separated as a distinct layer instead of mixing with limonene and precipitating the alkaloids (which is why FASI was invented).

Regarding the orange, you used the chloroform to pull from mimosa, yeah? So probably the chloroform dissolved other plant oils/fatty acids and thats whats making your dmt orange ? Or did you dissolve pure white dmt in chloroform and when you evapped, it became orange?
 
endlessness, extracted from mimosa with 3x hot 3% AcOH/EtOH, evaporated, dissolved in water, basified, extracted with CHCl3. The chloroform was more or less clear, like yellow/amber.
 
I would imagine that with that procedure, you are pulling more alkaloids and other compounds and this is the cause of the coloration. I use CHCl3 for extractions as well, and the white 'precipitate' on top as it evaporates is common. It does this regardless of the type of extraction. It did the same thing for a mint extraction I did. Ive not done a root bark extraction in some years, however, with grasses I get a dry powder if the CHCl3 is dry. I evaporate at room temperature overnight.

Also note that the acetates of DMT and 5MeO are soluble in chlorinated solvents and to some extent toulene as well. I've not tried xylene yet, but may soon.

-D.
 
Do you first extract with a polar solvent, redissolve in basic water and extract with CHCl3? Would you care to explain your procedure more deeply?
 
Adivino said:
endlessness, extracted from mimosa with 3x hot 3% AcOH/EtOH, evaporated, dissolved in water, basified, extracted with CHCl3. The chloroform was more or less clear, like yellow/amber.
Click to expand...

Acetic alcohol mixture ? Can you tell more about the amounts of chemicals used and pH levels ?
 
With the procedure that I use, I am interested in getting all the alkaloids out of the extraction that I can. This may be different than what you are trying to accomplish. The basic procedure that I use is a pretty straight forward A/B extraction:

5-10 gm chopped grass is lightly refluxed for 1h in MeOH @ 55C - X2
Filter
MeOH evaporated and residue dissolved in dilute H2SO4 - Ph 3
Filter
Defatted X3 with CHCl3
Made basic with NH4OH to Ph 11 -12
Extracted X3 with CHCl3
This is evaporated to (sometimes) leave powdery yellowish orange alkaloid mix (5-20mg estimated)
This is taken up again in MeOH (1ml) and used for TLC

With the grass (Phalaris) that I've been working with, this shows about 7 compounds on the plates.
I wouldn't necessarily use this procedure to target a specific compound like 5MeO or 2MeTHBC as it is a non specific extraction procedure.

From my understanding of the procedure you used, assuming it is on MHRB, you may be pulling some other compounds (phenols, tannins, etc.) from the material as well as a mix of alkaloids (NMT, DMT, etc.) and this maybe why you are getting an oily, orange/brown residue.

Also, by using AcOH, you are initially converting to the acetates which are soluble in CHCl3. If this is under basified, and some of the acetates of DMT (and I would imagine NMT but would have to check) are left in the solution when extracted with CHCl3, they may not form crystals and stay oily.
 
Dozuki, you are exactly right. I recrystallized from pet ether the residue from the extraction with chloroform, and indeed the precipitate is a brown oil. This may be the acetate you are referring to. I used AcOH/EtOH mainly because of a report of quantitative extraction from the DEA, but ethanol alone should be enough.

However, I basified with NaOH to 12-13 (which is by the way high). Do you think that AcO- has dissolved into the organic phase, forming DMT acetate (and other stuff) there?
 
Yes, EtOH works too. Ph 12 - 13 should be fine and should have converted the acitates to the free base, so I suspect that your brown oil is still a combination compounds. You can repeat the crystalllization a couple more times to see if that cleans it up. If not then you picked up a compound that is also soluble in pet. Ether. If this is the case, then you might need to convert back to a salt (preferably not the acetate) and then de-fat, basify, and re-extract.

If I were trying to get the most out of MHRB I would probably use a procedure similar to what I posted above and then take the alkaloids mix and recrystallize with heptane, hexane, or naptha.
 
Adivino, link to the DEA paper please ? I know only of one but there they use methanol for quantitation and acetic acid for isolation.
 
Shaolin, that is the paper. I used ethanol instead of methanol because of availability, and acetic acid to aid in the extraction.
 
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