I've performed a number of extractions using limonene, which was then salted with vinegar, the aqueous solutions combined and reduced to a smaller volume.

I don't know if it's a feature of limonene or impurities in it, but the liquid extract has a strong citrusy / limonene smell (which I used to like, but now find repulsive), a strong taste which makes me want to throw up right after drinking it, and gives me gastric discomfort.

I wonder if there is a way to remove the undesirable compounds from the extract?
I know I could always re-base it and pull with naphtha, but I'm trying to preserve the full spectrum, that's why I chose limonene and not naphtha.

As it is, I'd rather drink crude teas than this disgusting solution.

You could try to boil the aqueous solution until all the limonene volatilizes away.

You could also try to pull the limonene out of the aqueous solution using a vegetable oil.

But in practice the smell probably won't go away completely.

I suspect it's not the limonene, but the impurities in it, and they won't evaporate.
Pure limonene wouldn't have a citrus smell.
It's possible that the impurities migrate from the limonene to the aqueous layer and after reducing the latter they become concentrated. I boiled 800ml to 32ml, no wonder it's so nasty.

I might give sunflower oil a try, but if the impurities prefer water to NP solvents, that won't work.
Would heating be advisable?

Pure limonene most definitely has a citrus smell.

Many limonene oxidation/degradation products are not water soluble though some might be (source) Anyways I think trying out the vegetable oil clean up sounds good, you might remove whatever is bothering you.... You can first try no heat, see if it helps, then try with heat if it doesnt.

Thanks guys. I tried to clean it up with sunflower oil, but it didn't work.

The wash oil doesn't have the slightest hint of the abhorrent taste or smell, and the extract is the same as before with the only difference being sunflower oil contamination.

I guess I'll have to switch to xylene.

And you are planning on drinking something after putting xylene there? yuckkkkkk

Thats like cleaning dirt with garbage.

Xylene cooks off quite completely. Merely touching pure xylene doesnt taint it if the xylene is removed. Every day, people eat things that were washed with solvents like xylene or hexane. Its called processed foods and pharmaceuticals

If the impurities in the limonene are pre-existing and not artifacts of the extraction, and they are more soluble in acidic water than limonene, then the limonene could be washed with dilute acetic acid to remove the impurities immediately before extraction.
If, however, the limonene is reacting with your base and forming the impurities as you pull then your options are basically reduced to 1) try using a weaker base if applicable, 2) find a way to remove the impurities [eg. oil pulls, paraffin defat, further extraction, etc], or 3) use xylene.

If someone were intent on using limonene and only limonene, and it is strong base thats causing the impurities to form, an experiment could be done. Extract bark with limonene and salt to vinegar water as before, concentrate, then base again but with sodium carbonate, extract into a smaller amount of clean limonene, salt back to water, cook off residual limonene. If the contaminant were caused by pH >12 then the secondary, milder, B/A cycle should clean most of it out.

Another possibility that occurs to me is, could salting with an excess of vinegar and heating the vinegar with limonene be whats producing the contaminant? I'd assume it to be the less likely scenario, but thats something that could also be explored.

Thats all theoretical, I've still never seen limonene in my country. I did finally find a bottle that said 'Lemon Oil' but it contained high boiling petroleum ether and synthetic fragrance

I would imagine Jagube doesn't have a pharmaceutical /industrial food processing set up with rotovap or similar, so your analogy doesn't work well. While xylene theoretically will boil off, from my own personal experience it tends to linger significantly, and having xylene burps during a trip is not fun at all

Each one to their own though

Xylene burps would disturb me. Xylene vomit would disturb me even more

I've cooked xylene off DMT hydrochloride or fumarate solutions several times and never detected even a hint of residual xylene. Perhaps its an issue of technique?
When gassing off the xylene, instead of boiling, I always put the liquid in a beaker and set it on a coffee maker hotplate for several hours to gradually reduce. Half the way through I carefully poured it off to a smaller beaker just in case any micro droplets might have been adhering to the side of the beaker under the water.
The xylene odor was always long gone by the time I stopped, though I reused a batch of xylene from a cactus extraction when making DMT fumarate solution and now I have frozen DMT fumarate stock that smells like orange mescaline, I almost like it

I don't think the impurities are pre-existing. I used this limo on an MHRB extraction first, and then on a Phalaris extraction. If the impurities were pre-existing, the first extraction would have cleaned it up, but the second extraction is as yucky as the first.


Sounds like an idea to try, but isn't sodium carbonate too weak to freebase DMT and the co-occurring alkaloids I aim to extract? Or is it only a problem with crude teas and not so much with my already relatively clean (if yuckier tasting) product?

Another factor which may be contributing to the yuckiness is the pH around 4.4; would it be advisable to add some base to make it less acidic?

I havent tried it on a quantitative basis myself, but the consensus on this forum is that once the tannin and other competing planty stuff is out of the picture sodium carbonate is strong enough.

I've tried Elrik's suggestion of re-basing with sodium carbonate and re-pulling and it didn't work; the product is still as nasty as the original one. I've done it at least twice now and got the same poor results.

It seems it's not the oily fraction of limonene that contaminates it, but something that migrates from the limonene to the acidic solution along with the DMT. Whatever it is, it's not oily, it's water soluble, smells strongly of limo (absolutely horrible when concentrated), has a repulsive sour taste and drinking even a drop of it gives me stomach cramps. The solution is yellow, or amber at higher concentrations, but I don't know if it's due to the limo nasties or something else (could even be the alkaloids).

Now I've reduced some nasty limo pulls to a small volume and I'm drying them in a heated propagator. The idea is to evaporate all the water and acetic acid and be left with DMT acetates and limo nasties (and possibly other impurities) only. There is also a chance that some of the DMT acetate may freebase?

But what can I do with it once it's dry to separate the DMT from the limo nasties? Can I add a bit of ammonia solution to base it and then put it in the fridge to crystallize out the DMT?

Limonene is far from inert as a solvent, unfortunately. It slowly oxidises and these oxidation products are of greater polarity than limonene itself. This means they're more soluble in the DMT acetate solution than limonene ever would be.

I've tried working with aged limonene before and encountered the same problem. Those aroma compounds are very sticky and the taste is very off-putting. In order to clean up your product, you will probably have to recover it as the solid fumarate salt and rinse that with ice-cold, bone-dry acetone.

And that's a fair amount of work.

Washing the present liquid extract with diethyl ether would probably clean it up, but that then involves obtaining and using ether...

I don't need it pure, just to take the edge off the taste. Would just salting it out with fumaric acid and skipping the acetone wash be sufficient?

I've dried the extract and it doesn't smell of limonene anymore. It has white small particles in it, which I initially thought was an alkaloid in freebase form, but they don't dissolve in vinegar.
I ingested a little bit of it and it didn't taste that bad.

Update: took more and had my first proper Phalaris AQ1 experience without discomfort. Whatever it is in the limonene that gives it an off-putting taste, seems to evaporate cleanly enough for the purpose of oral ingestion.