Fumaric acid soxhlet extraction.

[Sarenace]

Good day.

I used to extract DMT in my 20's using a simple acid base setup that i designed myself (im an ex biochemist and I was unaware that there were such good resources online). I subsequently forgot about DMT for many years. Im now in my 40s, and my colleagues are asking about DMT. I have found that researchers on this site have discovered that the fumarate salt of DMT is insoluble in various non polar solvents. Ive also discovered that since becoming a father with full time employment I have less free time for a full acid base with multiple acid washes, defat pulls and so on and so forth. As such I wanted to run an easy extraction tech past you guys that I dreamed up to see what you thought, and get some advice.

The tek is a basic soxhlet extraction using a volatile non polar solvent saturated with fumaric acid. Fumaric acid has a very high boiling point, above 500 degrees, and as such will not boil off to the condenser. The solvent will boil off, hit the condenser, where it will condense, and then flow into the extractor where it will pull DMT from the plant material. The DMT containing solvet will then flow back to the boiling flask where the DMT will react with the fumarate and drop out as an insoluble precipitate. You just set the thing up with about 100g of powdered bark, fire up the heat, and leave. I have 3 versions

-Straight to Acetone version: To a soxhlet extractor is added powdered DMT bearing bark, whilst the boiling flask is filled with a saturated solution of fumaric acid in anhydrous acetone. The theory is that many DMT salts would be soluble in acetone. If they werent, you guys would be using mallic or oxalic acid in lieue of fumaric to form precipitates. As such, it is possible that we can dispense with acids or bases altogether and extract straight into acetone. This is my favourite version for its sheer simplicity.

-Straight to base version: To a soxhlet extractor is added powdered DMT bearing bark, whilst the boiling flask is filled with a saturated solution of ammonium fumarate in a suitable non polar solvent (this site leads me to believe either IPA or Acetone are the promising candidates). The theory is that the the heat will drive off the ammonia from the ammonium fumarate, and as it is a volatile compound, send it up the column to the condenser where it will redissolve in the solvent, basifying it before it hits the bark. The advantages are that it sidesteps the question of how soluble DMT salts are in acetone, the ammonia will freebase the DMT; and that metal generally does not react with ammonia allowing the aspiring psychonaught to retask a common pressure cooker or home alcohol still to the extraction. The disadvantage is that I have no idea how soluble ammonium fumarate is in either acetone or in IPA, and I dont know if heat will be enough to decompose the ammonium fumarate salt. Its possible that a small amount of strong alkali, like sodium hydroxide, could be added immediately prior to the extraction to help drive off the ammonia. Could I get you guys to weigh in here?

-Straight to acid version: To a soxhlet extractor is added powdered DMT bearing bark, whilst the boiling flask is filled with a solution of a non polar solvent saturated with fumaric acid and hydrochloride gas. Hydrochloride gas may be added by simply dumping in fuming hydrochloric acid and then drying with excess anhydrous magnesium sulfate, or some other drying agent (could you guys weigh in on this method?). Fuming hydrochloric acid is commonly available at hardware stores in Australia; if you're not from Australia, I cant help you. The theory is that hydrochloride is a volatile acid, and heat will force it into the condenser as for ammonia. The advantages are that there is no need to consider the solubility of some fumarate salt; hydrochloride and fumaric acid are both acids and dont form a salt; and that the hydrochloride may be easily added by simply adding in fuming acid and then drying. The disadvantages are numerous. Hydrocholride gas reacts with metal, ruling out a homebrew set up patched together from a pressure cooker or alcohol still- proper glassware or stainless steel may be required. I have no idea how soluble dmt chloride is in Acetone or IPA, so there may be no extraction at all (I do believe IPA will probably dissolve a small amount of DMT chloride as it is a protic solvent). Hydrochloric gas is quite dangerous if inhaled. If it works, however, it will be the only example of a straight to acid tek.

Ok so thats the idea, using heat and a condenser to continually recirculate a solvent through the plant matter and having fumarate in the boiling flask so dmt fumarate drops out of solution. The setup could be left to run over night, and then filtered in the morning, greatly simplifying extraction.

As mentioned above, Im thinking the aspiring psychonaught could retask an electric pressure cooker to the extraction, by pulling the knob off the steam release valve and connecting that to the condenser (This is possible- in my teens my uncle was an apiarist. He would cut the caps off the bee wax using a steam heated knife connected to a pressure cooker; me and my cousins used to steal his pressure cooker and steam knife and use it to make moonshine, so I can assure you this works). The soxhlet may evacuate back into the pressure cooker via the pressure indicator valve, I imagine it could be removed via a grinder. Alternnative one could simply add copper inlets and outlests by drilling through the lid. Electric pressure cookers often have temperature settings and timers, and they can be set up outside, to mitigate fire risk. A home made pythagorean cup would have to be added.

Could I get some feedback on this tek?

 

[downwardsfromzero]

Soxhlet extraction of bark has been talked about from time to time for years now. The main thing to consider with Soxhlet extraction is that it is aimed at extracting substances of limited solubility. This designation does not apply to DMT salts in water, or freebase DMT in acetone or IPA. Add to that the fire risk of running, in particular, an acetone extraction and you'll realise that leaving it unattended is unwise. This eliminates any time gains you may have envisaged.

metal generally does not react with ammonia

one could simply add copper inlets and outlets

Copper forms an oxide layer in air which is readily soluble in aqueous ammonia, forming cuprammonium hydroxide (which, incidentally, will dissolve cellulose). I would not use ammonia with copper, brass or bronze apparatus. Zinc also forms soluble complexes with ammonia, as do a good number of other transition metals. Given this information it shouldn't be to surprising to hear that a significant application for ammonia solution is metal cleaning.

Another thing to bear in mind is the reactivity (when compared with isopropanol) of acetone. It is not really compatible with ammonia or hydrochloric acid.

I would also discourage the use of gaseous hydrogen chloride without proper equipment.


More or less prolonged soaks of plant material in some solvent or other may be a viable option for you. Take a look at, for example, this:
Extracting DMT with ethanol, vinegar and sodium carbonate
for a few ideas, which you could maybe combine with some principles form, e.g. here:
The FASA Method: A Summary - DMT Fumarate and Beyond

There's also some interesting reading to be had here:
2019 paper using hexane, ethyl acetate, and other solvents

As far as 'one stop' solvents go, ethyl acetate seems to be among the most promising.

 

[Sarenace]

Is the fumarate salt of DMT insoluble in ethyl acetate? I mean thats the whole plan. When the soxhlet releases the solution into the boiling flask it reacts with fumaric acid to produce an insoluble precipitate. Fumaric acid has too high a boiling point to end up in the soxhlet, so you set the thing up, let it run, and there should be dmt fumarate crystals in the morning, easy as pie. If the fumarate is soluble in ethyl acetate, its almost a non starter. Im looking for the simplest most labour unintensive extraction I can design, and if it works, share it with you lot. Ultimately, Id like to find a viable way of extracting phalaris, and therefore eliminate the need to harvest natives.

 

[Dozuki]

If you have a Soxhlet, it would be easy enough to give it a try. I don't think I would try and build one just for test though...

-D.

 

[downwardsfromzero]

If you have a Soxhlet, it would be easy enough to give it a try. I don't think I would try and build one just for test though...

-D.

I have a whole selection of Soxhlets of various sizes and still can't be bothered to try anything like this :lol:

It remains to be seen whether this says more about the method or my laziness, of course. But I can say that a Soxhlet seems to work well enough with acetone and hemp flowers.

I think the solubility of the fumarate in whatever solvent is mostly a non-issue; the main thing is that whatever you want to stay in the flask is non-volatile at the boiling temperature of the solvent system being used.

You may find some further useful information here.
And here and here.

There's another recent thread which goes into using various other organic acids a bit but I'll have to dig that out later.
[EDIT: I think it's this one: Lazy alkaloid salting combos (CISLO) - Collaborative Research Project - Welcome to the DMT-Nexus ]

 

[Dozuki]

I think the solubility of the fumarate in whatever solvent is mostly a non-issue; the main thing is that whatever you want to stay in the flask is non-volatile at the boiling temperature of the solvent system being used.

Ethyl Acetate was what stuck with me reading the OP. Thanks for the links, good info there.

I'd also think you would have to play with the level of saturation of the solvent with fumaric acid since you'd be dealing with boiling temps of the solvent vs cold temps?

I have a whole selection of Soxhlets of various sizes and still can't be bothered to try anything like this

I have a soxhlet, just not the acid. Interesting concept tho.

-D.

 

[downwardsfromzero]

As far as time pressure goes, with powdered bark it's fairly easy to get to the stage of having pulls in the freezer with one hour using a standard STB method at the 50g scale. Just sayin'. The time required for setting up the Soxhlet needs to be factored into the comparative equation - and it's just not a good idea to leave flammable solvents refluxing unattended. But I may yet give some iteration of this method a try, it's kind of been somewhere near the lower middle of the bucket list for years now.