Experimental: Extracting mescaline carbonate bubbling CO2

[modern]

So I've already tested and know that mescaline carbonate is insoluble in water (atleast in small volumes) So I've tried doing adding vinegar slowly to try and get ph low enough to get carbonate after alkalinizing with sodium carbonate but didn't work just a mess really.

So I came up with this idea. Make a tea. Reduce carefully not to caramelize the sugars. Then add calcium hydroxide slowly until ph 11-12 and filter. (First image) I saved this since the mescaline may be trapped in here so gonna do alcohol extraction to test.

Then I did a DIY CO2 generator to bubble CO2 for around 20H until the ph paper showed 6-7 ph and there was a very fine precipitate on the bottom. IT MAY BE calcium carbonate so I need to test still.

I added a ice bath to increase co2 solubility but idk if it helped any.

I decanted but the powder is so fine that I had to centrifuge the solution using a fan for 10 minutes so it all sticks to the bottom.

I was gonna add some alcohol and evaporate but my only evaporating watch glass is busy with my ethylene experiment.

Anyone think this is viable? I will find out regardless but thought I'd share since someone might have some insight. I'll probably acidify with hcl and test this way. I don't have any TLC plates left to test with the reagent spray. IDK if spraying directly would result in purple shading?

 

[Transform]

Great to see you experimenting some more. Could you provide a link for the carbonate solubility experiment, since it would be handy to have a link to it in your first post.

Yeah, that first idea really wouldn't work - as you've now found out, although I can see the logic of attempting to perform a 'double decomposition' on mescaline acetate with sodium carbonate. I'd advise using straight mescaline acetate solution for repeating that experiment.

It's plausible that some residual dissolved lime may have come through and formed calcium carbonate, although that would start to convert to the soluble calcium bicarbonate at the pH you used, hence that may not be what your precipitate is. Double - check by re-suspending it in distilled water and repeating the CO2 bubbling. If it dissolves, it may be calcium carbonate. A drop of vinegar will also reveal the presence of a [significant amount of] carbonate if it starts fizzing/effervescing.

It's sort of unfortunate that you're relying on producing an insoluble/poorly soluble compound while also using a process which introduces an impurity that easily may form another insoluble compound.


Evaporation - if you can find any glass object with a concave bottom - most preferably one which can stand stably by itself when turned upside down like many preserving jars) - you can use that as a makeshift 'watch glass'.

 

[modern]

I have formed freebase and it made carbonate since freebase is like an oil like substance atleast for me. The easiest method to see the carbonate was via h2o2 to remove the oxalate. It forms carbonate and I have around 200-300mg in 15mg of water/h2o2 that is a fine powder.

I took this approach to assuming the calcium hydroxide with the extremely limited solubility in water would convert to calcium carbonate then calcium bicarbonate which has fairly high solubility. I’ll try to weigh the resulting powder and convert to hcl and weigh in hopes to atleast see possible “contamination” rate which I’ll be minor and nontoxic.

I used an untested cutting to test first run instead of pure product which I’ll back test later. I theory I think this should work… maybe sodium carbonate would be a better option or sodium hydroxide and bubble co2 for a day or two?

This may be better as a cleanup for acetate tar or something? I used like 300g fresh so like 10g dry so small yield expected. I have others move around where I setup só risk of spilling and such prevents some options for me. I always go diy route when possible

 

[Transform]

Hehe, that's what I love about your experiments - the adherence to the DIY ethic wins a special place in my heart.

More thoughts after I've slept.

 

[_Trip_]

Love the centrifuge fan.

 

[modern]

Hehe, that's what I love about your experiments - the adherence to the DIY ethic wins a special place in my heart.

More thoughts after I've slept.

Not diy by choice but necessity… everything lab related is 50% more expensive in just 2-3 years :/

So I collected all the precipitate in a Single container and another decant of the main liquid. All together around 10ml liquid. I added isopropanol and a precipitate formed which I’m certain in calcium carbonate. So from here I’ll evaporate It a bit and add hcl so the solution should become clear. Then evaporate completely try to weigh and then isopropanol wash keeping the mescaline hcl.

Assuming I get around 30-50mg of hcl that should be close to complete yield based on other cacti of mine. I might have been able to use my lab filter but so small amount that didn’t seem worth it.

 

[Transform]

Not diy by choice but necessity…

Fully understood - it's situations like yours as much as mine that underpin my own commitment to communicating the fundamentals of chemistry. Knowledge is power, and with rocks, fire, plants and a bit of ingenuity we can achieve a LOT even without access to much lab equipment.

I added isopropanol and a precipitate formed which I’m certain [is] calcium carbonate

But calcium carbonate is already completely insoluble - I think you need to consider the possibility of it being another salt, like the malate or sulfate perhaps, or a different cation.

 

[modern]

Fully understood - it's situations like yours as much as mine that underpin my own commitment to communicating the fundamentals of chemistry. Knowledge is power, and with rocks, fire, plants and a bit of ingenuity we can achieve a LOT even without access to much lab equipment.

But calcium carbonate is already completely insoluble - I think you need to consider the possibility of it being another salt, like the malate or sulfate perhaps, or a different cation.

calcium carbonate does have a very small solubility in water but indeed seemed more than it should have been. Isopropyl maybe even dna precipitated?

Regardless I tried filtering but gave up and added hcl until it all dissolved. I’ll evaporate it all then wash with isopropyl then maybe a tiny xylene a/b. I’ll run a TLC on it… with the remaining tea I’ll run a xylene extraction just be sure.

I should have started with pure salt like I did with oxalate. On paper I think it may work but I’ll need to repeat using a crude tea extract or pure mescaline to test. Maybe tea just has too much junk for this method.

Is it possible it’s another salt? I thought that calcium hydroxide would neutralize them all?

 

[Transform]

Maybe tea just has too much junk for this method.

That may be the case, although some careful thinking (backed up by literature) about what can be going where may help you to design a succession of stages where you coax the target molecule into a desired state of purity.

Is it possible it’s another salt? I thought that calcium hydroxide would neutralize them all?

Other inorganic salts would be largely unaffected, although some sulfate might get held back in the lime stage since calcium sulfate has a poor solubility (2.6g/L). There may be enough CaSO₄ present for it to precipitate with addition of IPA. As for organic anions, it depends on the solubility of their calcium salts.

Inorganic cations, especially sodium and potassium, will carry over into the aqueous solution, so there's a possibility of precipitating a bicarbonate of either or both of those two. Bicarbonates can also co-crystallise with carbonates as sesquicarbonates, so it may be worth checking the solubility curves of all the permutations in that system. Suffice to say, sodium sesquicarbonate is less soluble than both the carbonate and the carbonate of which it is comprised.

The presence of quaternary ammonium compounds cannot be entirely excluded, since they are known to occur in various trichocereus species. These would be capable of forming carbonates of which the solubility profiles remain to be determined, and naturally depend on the identity of the cation in question. [Given the commercial availability of tetramethylammonium carbonate (albeit as a 25% solution), formation of other quaternary ammonium carbonates seems entirely plausible, at least.]

 

[modern]

So another unknown precipitate formed in the original tea. I did already remove pectin but could be some more maybe. Not as heavy as pectin.

I added hcl to the iso/tea/precipitate mix and today there was some very shiny crystals along with some dirty precipitate. I’ll allow it to evaporate completely then try to weigh before attempting filtering. Will probably be another week or so.

Can’t get a good photo of the crystals that appeared in the treated precipitate

 

[Transform]

So another unknown precipitate formed in the original tea. I did already remove pectin but could be some more maybe. Not as heavy as pectin.

I added hcl to the iso/tea/precipitate mix and today there was some very shiny crystals along with some dirty precipitate. I’ll allow it to evaporate completely then try to weigh before attempting filtering. Will probably be another week or so.

Can’t get a good photo of the crystals that appeared in the treated precipitate

That photo shows something, at least, and it looks quite interesting…

It will be good to see what a reagent test shows once you get the crystals filtered off and washed.

 

[modern]

That photo shows something, at least, and it looks quite interesting…

It will be good to see what a reagent test shows once you get the crystals filtered off and washed.

That is not from the co2 bubbling but after I reduced a little more and stopped bubbling... The co2 should have almost completely been removed from the water

The actual precipitate had lots of dirty precipitate that formed so I added a bit more hcl to free any possible acids and filtered to remove a brown precipitate that remained.

 

[modern]

So all the precipitate that was formed from the co2 bubbling was collected after a fan centrifuge was done. This was then all joined and concentrated hcl was added to free any acids that bonded to the mescaline and other salts.
This was then left to air evaporate slowly over the past month and there was quite a lot of precipitate that remained however was all in form of grains. So I added water and filtered off. As I write this I realized this may be mescaline carbonate that didn’t convert to mescaline hcl. Regardless I could also see quite a bit of fats/oils relative to the quantity of salts.
Now after allowing this water to evaporate I can see some crystals with some impurities.
This extraction path seems plausible and I’ll consider reattempting this extraction experiment since it shows some promise.

The first two photos are the water filtered hcl salts after the first hcl salting of the carbonates. The last dish is hcl saying if xylene extractions in the tea to see if a majority of the salts didn’t stay behind.

 

[modern]

After another crystallization and filtering I have very clean crystalline material that looks similar to my cleanest hcl material. I ended up with around 35mg of hcl salts which is around the average mescaline yield I'd expect of around 0.4% or less % of the dry material.

I'll get around to doing the Ninhydrin stain on tlc in the future and will save this material separately. Will be a while. The xylene water fraction is showing some crystals which I think it the 'other' alkaloids I generally get which I'll also test in the future by solubility properties and later the stain as well.