So my neighbour's crazy friend has been at it again! There's one part of the report I've not seen mentioned in any way anywhere else before - using basic, wet IPA to pull from limonene.

Apologies for the length of this post - I've put a summary of important points at the end of the post.


Here is a report in brief of his latest story:

"*oxidised solid DMT collected from on top of 3yr old MRHB/STB.

*dissolved in dH2O/ascorbic acid solution forming a deep orange solution. Simmer 5mins. Add a suitable amount of NaOH.

*cool and extract with light naphtha - but do not remove naphtha from the surface of the liquid. Stopper well - but not completely airtight - and refrigerate for a total of about 3 years.

*less than halfway through the refrigeration period, all the naphtha has evaporated, leaving a suspension of curdy precipitate resembling mould/yeast infection.

*place in a water bath and bring the temperature up to 100degC. The curdy precipitate redissolves and the orange colour of the solution becomes more of a deep yellow.

*allow to cool, then place back in the refrigerator. Subsequent observation shows return of the curdy precipitate, plus small crystals have formed in the same area/volume. This indicates it wasn't mould - not so surprising at pH >10.

*maybe repeat the heating step a year later.

*temperature cycling between 4degC and room temperature produces enlargement of the crystals to a maximum of about 2mm x 1mm.

*at some point when the time seems right, add a couple more spoonfuls of NaOH and a requisite amount of NaCl. Place in a separatory funnel and extract with 6 portions of limonene. The limonene turns cloudy, but the insolubles soon settle out to form a layer between the limonene and the aqueous phase leaving only a slight haze in the limonene.

*drain off the cloudy material and put to one side in a tall, thin container, e.g. a large test tube. More limonene will float off from the insolubles, and more aqueous solution will drain beneath. Use a pipette to transfer the limonene in with all the rest of the limonene. Use another pipette to transfer the aqueous phase into the bulk of the same - which was kept (haven't you??)

*back-extract the combined limonene pulls with 5 portions of 5% acetic acid.

*put all the acetic acid pulls into a a broad pyrex dish of a suitable size and evaporate to dryness using standard methods, e.g. computer fan and reptile heating mat works well. It stinks of vinegar while this is taking place.

*scrape up acetates and marvel at how little there seems to be. Now look back at the limonene and see how orange it still looks. Hmmm....

*going back to the tube of curdy gunk, an amount of isopropanol was added and the tube was swirled to mix. This caused the limonene to float to the top, in between was a layer of IPA and at the bottom was the aqueous phase, with the gunk floating between the water and the IPA.

*both the limonene and the IPA were virtually crystal clear - all the cloudiness had been pulled down to the aqueous part - but... virtually all the orange coloration had been transferred to the IPA phase!! The limonene had only a very slight yellow tinge remaining.

*this was scaled up in order to wash the limonene: the vinegar extracted limonene was washed with saturated sodium carbonate solution (3 to 4 potions making a volume about half that of the limonene). The washes were kept. Isopropanol was mixed with the saturated sodium carbonate washes. Further anhydrous Na2CO3 was added. Two layers formed and the upper, IPA-rich layer was added to the limonene in the separatory funnel.

*lo and behold! Three layers formed - the limonene clear and pale yellow, the IPA now a deep orange and the water cloudy and only a very faint yellow. The layers were separated and placed into stoppered flasks.

*presumptive testing of the IPA showed a result corresponding to that which might be expected from DMT.

*the IPA was dried with anhydrous sodium carbonate powder, then carefully decanted into a test tube to settle thoroughly. After settling, the IPA was removed by pipette and placed into a suitably sized Erlenmeyer flask.

*FASA was added. A thick white precipitate immediately formed. At some point a further test drop of FASA to the solution did not produce any further turbidity.

*the flask was allowed to stand for a couple of days, during which time the precipitate clumped together in bigger lumps but refused to settle out or become crystalline."


The question here is how to procede and separate the precipitate from the liquid?

Filtration is considered too tedious (ironically!!) and risks yield reduction. Perhaps temperature cycling may help to grow the crystals, e.g. hot water bath, slow cooling, fridge, then freezer, repeat if necessary.

Decanting into a test tube may also help, although the crystals are then stuck at the bottom of a tube.

Any other suggestions?

Summary:

* Ascorbate appears to reduce oxidised DMT under alkaline conditions.

* There is a byproduct which seems to be insoluble in water, limonene, IPA and acetone.

* Basic (Na2CO3) wet IPA extracts DMT and orange coloration from acetic acid washed limonene, forming three phases.

* The IPA extract after drying produces abundant precipitate with FASA.

* Refrigerating for 3 years is probably unnecessary

Turns out it was probably sodium fumarate... [laughs madly]

You probably just had some unoxidized dmt with it that got salted. Maybe?


What did this byproduct look like?


Was this the sodium fumarate you just posted about? lol


Refridgerating only slows down the process of oxidation.

Wow thats what you call playing the long game some mad scientist shennanigans for sure i think youve just turned my otherwise crappy day around

And you, my friend, have made my day too! Thanks for the reply.

I think this guy is not too concerned about getting quick results. The science of s...l...o...w reactions can easily be overlooked, although I'm not convinced he's made any breakthroughs here! Managing to keep a bottle of brown curdy liquid in the fridge for three years without it getting thrown out is something of an achievement, however

I am told his yield of acetate from the vinegar washes was 190 mg of... something. This took him a total of six years to achieve

There certainly wasn't any quantitative data from the start of the experiment, so really it would only be fair to call it an inference based on the observation of the solution going a paler yellow from a deeper orange colouration, kind of a reverse of the colour change seen when DMT oxidises/is thought to oxidise.

As stated in the method it was a curdy white precipitate.

Quite possibly yes, although some basic level of analysis would be required to state that it was exclusively sodium fumarate. The moist IPA will certainly have contained some sodium ions, probably as carbonate - although when I discussed this matter recently I was told that the sodium carbonate had been made from sodium bicarbonate and a bit of extra sodium hydroxide had been added to the solution as there were concerns about the completeness of the conversion. So there was in all likelihood a bit of hydroxide present the solution, too. The precipitate could in all likelihood contain a trace or more of DMT.

Come to think of it, could IPA possibly extract NaOH preferentially from a mixture with Na2CO3?


That's probably another reason why it was stored in the fridge, besides attempting to encourage crystallisation; the reduction occured (or appeared to occur) when the mixture was heated on the hot water bath.

The rationale behind the reduction phase of this experiment was knowing that ascorbic acid is more rapidly oxidised at alkaline pH (so I'm told). Therefore ascorbic acid must be a more effective reducing agent at higher pH.

And remember, dear people, besides the interesting lightening of the orange colour to a yellow shade by heating known-to-be-oxidised DMT in alkaline solution with ascorbic acid, the other interesting observation (IMHO) was how the orange/yellow colouration of used limonene could be removed by washing with basic - i.e. alkaline - aqueous (wet) IPA.

I would suggest a final step, after ensuring that all precipitates have precipitated, is rebasification of the precipitate and extraction into anhydrous acetone or IPA.

Let's see how long that takes

EDIT: Maybe a last blast FASA on the limo too?

Thats really good to hear! I totally misunderstood the 2 times you said it was 3 years old. I thought you meant 3 years total. So it was 3 year old bark that was in turn refridgerated for 3 years. Wowza.

Hm. maybe some pigmentation of the bark took part in the orangification(scientific term, i know) of the limonene? Or possible the abscorbic acid had a dye in it? Dont know. Good to hear it was fixed with a basic wash though.

Actually the bark was one year old, then it sat as alkaline sludge for three years after 3 naphtha pulls. Then crystals were picked off from around the mouth(s) of the jar(s) and subjected to the procedures described in the thread. So 7 years!

The limonene pull described in one of my other threads was also from this batch. Don't know how much bark was used to start with but, in total, near enough another gram of something has been recovered from it, 6 years later!

Here's another belated update: the extraction of the orange stuff into an aqueous IPA phase, which floats between the water layer and the limonene layer has been confirmed experientially on several occasions. So, if there's anyone out there who wants to fiddle around with the orange stuff, they could try partitioning it out of sodium carbonate and sodium chloride solution with isopropanol.

Aqueous isopropanol is immiscible with limonene and immiscible with saturated sodium carbonate/chloride, although some isopropanol will be dissolved in the other two layers.

I thoroughly commend the unwaivering commitment in this process It is truly the 'Game of Thrones' of extractions it could well be just a complex congealment of different substances but PLEASE PLEASE recommend the researcher keeps a bit of each for TLC analysis! You just never know what might turn up, it could even be left to mold and then test the mold for tryptamines.
Seriously ,call the 'Guiness Book of Records' or not "Hi I believe I have the longest kept mimosa sludge in modern history!" "Certainly we'll send someone around to inspect it" I can imagine having some rep poke and prod at the sludge in its magnificent glory pontificating on whether it may be a record breaker.

My god, people are still actually reading this stuff!

"Unwavering commitment" - that's putting it very kindly. I would have said "bungling indecision" but I can be a bit harsh sometimes.

It turns out this guy has recently re-discovered his little pots of stuff after moving house. The question now remains: what could be done with the orange IPA? Acidify, evap and re-basify for acetone extraction?

I'd like to find out if it's got 2-MeTHBC as a significant component. Hope he knows his TLC.

Unfortunately, as far as the Guinness book of records goes, the original sludge was ditched several years ago, after the crystals were picked off the top.