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Lime for STB doesn't work with heptane?

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modern

Esteemed member
So I've tried a straight to base using calcium hydroxide to base and ph is easily 13. I've added heptane but zero precipitate formed from freezing for 24h-48h at -20C. I've tried adding vinegar to the heptane to salt out and will check if it forms an acetate.

Do I need to add lye to my mhrb or should the Lime work? I've seen lime used for ethyl acetate pulls so thought it would work with heptane
 
Lime does not work with naphtha, I tried.

It should work based on pH, but it does not. I think the DMT is encapsulated inside some kind of plant matter and lime/naphtha doesn't break that down. NaOH or ethyl acetate can dissolve that (hypothetical) protective layer away.

Welcome to the subtle complexities of working with biological systems and gentle chemicals.
 
Lime only works with naphtha if you're recovering DMT from an already extracted salt form. So, it could be used in the second stage of a mini A/B cleanup, for example. This lends itself as supporting evidence for Loveall's encapsulation hypothesis to a degree, although there could be some other reason for naphtha's lack of utility there. One that springs to mind is that it is insufficiently polar to penetrate the plant material, which is ever so subtly different from what Loveall suggested.

[Thinking about this a little more, it could be the case that a layer of calcium tannate is formed which for naphtha is impenetrable but more polar solvents garner sufficient intermolecular interactions to be able to pass through. Quite amazing, really, that limonene is just that tiny bit more polar to be able to do this (or whatever 😁 ).]

Now a bit of good news: if you stir in some sodium carbonate (washing soda), the extraction - still using naphtha - will 'magically' work again. Actually it's metathesis rather than magic, and sodium hydroxide gets formed in situ. With any luck this should bring your extraction back onto an even keel; you may want to apply gentle heat using a water bath to ensure success (no naked flames, though!)
 
Right thanks for reminding me... I did this mistakenly when doing cielo and it didn't cause the ethyl acetate to breakdown as far as I could tell.

EDIT: Can I use sodium carbonate to base and pull with heptane or same issue as Lime?
 
If you have SC, lime, bark and heptane/naphtha you will simply get better results by combining the SC and lime. I can assure you that it will work, whereas I can't say the same for SC alone. Again though, you could try a parallel test with just SC as the base in one small portion and both SC and lime in the other. Minimising the use of materials is obviously desirable.

Looking a little more closely at the idea, we can see that there are several permutations to the order in which the lime, SC, bark and water can be combined. Listing them all here is probably unnecessary, but if my memory serves me correctly the sequence bark, lime, water, SC should be effective, with mixing each time an ingredient is added - but I'll have to be honest here: I forget whether the SC was perhaps added first.

Furthermore, a far less granular variable is then the actual proportions of these ingredients. All I can say is, it doesn't have to be too precise, merely sufficient, but you can always have a little play around with molecular weight calculations.

Be sure to report any results should you try this, and that includes failures.
 
I think sodium carbonate is tricky because it will begin to buffer with its reaction with other plant stuff forming sodium bicarbonate. Risk of not reaching high enough pH, depending on water concentration and other factors. More water and more sodium carbonate may make it work. Drier conditions could see a big buffering effect with the smaller ammount of sodium carbonate in solution being overwhelmed by plant buffers.

Soduium carbonate works well when doing a mini A/B or fumarate conversion though.
 
downwardsfromzero said:
Lime only works with naphtha if you're recovering DMT from an already extracted salt form. So, it could be used in the second stage of a mini A/B cleanup, for example. This lends itself as supporting evidence for Loveall's encapsulation hypothesis to a degree, although there could be some other reason for naphtha's lack of utility there. One that springs to mind is that it is insufficiently polar to penetrate the plant material, which is ever so subtly different from what Loveall suggested.

[Thinking about this a little more, it could be the case that a layer of calcium tannate is formed which for naphtha is impenetrable but more polar solvents garner sufficient intermolecular interactions to be able to pass through. Quite amazing, really, that limonene is just that tiny bit more polar to be able to do this (or whatever 😁 ).]

Now a bit of good news: if you stir in some sodium carbonate (washing soda), the extraction - still using naphtha - will 'magically' work again. Actually it's metathesis rather than magic, and sodium hydroxide gets formed in situ. With any luck this should bring your extraction back onto an even keel; you may want to apply gentle heat using a water bath to ensure success (no naked flames, though!)

One theory I have is that DMT is encapsulated in a biological membrane (cell wall or similar fatty acid). Limonene and EA can break into it down by dissoliving it away. NaOH also breaks it down, but by a different mechanism (saponification). Note that sodium carbonate can also saponify, but I can't find any references for lime doing this - so it seems to fit experimental results.

This is purely a guess. No evidence. Could be wrong. Fun to think about though.

Modern, a freeze/dry cycle can also break down cell walls and may make lime successful. You can try this if you still have the bark+lime.
 
Loveall said:
One theory I have is that DMT is encapsulated in a biological membrane (cell wall or similar fatty acid). Limonene and EA can break into it down by dissoliving it away.
Could EA be used to break down the biological membrane, let the EA evaporate, then proceed with lime and heptane?
 
I added the sodium carbonate and indeed the 'water' became black which seems right before it was grey.

From here I added the heptane and for now just keeping it seperate will freeze to see if it precipitates. It remained very clear but doesn't discourage me since heptane is super selective?

With the alkaline soup I added ethyl acetate and am doing two pulls. EA shouldn't be mixed with lye HOWEVER I didn't have an issue in the past with it breaking down. I added vinegar to the EA and and gonna evaporate it. If the vinegar has a good amount of salts Ill try cleaning it up with heptate. I may opt to use EA and only use heptane to clean up since I lost quite a bit of solvent (most likely due to errors on my end) EA is easier for me to obtain than heptane although about the same cost.

I'll update on what I end up.
 
So I pulled twice with around 200mL EA then I added vinegar to salt out and ended up with a pink lemonade liquid. I then added lime water and it turned purple. I pulled with the same heptane that I used earlier so IDK which of the pulls worked. I froze and it produced some nice looking very white crystals.

I'm redoing again with lye this time to base and the color difference was massive being very black soup this time. I'm using the same heptane which didn't have any 'lose' this time. I believe that the lost heptane from previous attempt was lost in the bark or something idk why I lost so much.

I'll likely only use lye and heptane for my future attempts. Sodium carbonate and calcium hydroxide do make sodium hydroxide and calcium carbonate but there seems to be a difference in the two since ethly acetate doesn't break down in the combination.

The first attempt bark wasn't repulled and just discared as a failure since it became a goo after the ethyl acetate pulls similar to cielo. There was likely a bit of alkaloid remaining but that is fine.
 
Heptane remained completely clear after I added to my mhrb soup. I'll report back. I thought heptane was so selective that it remained clear.
 
modern said:
So I pulled twice with around 200mL EA then I added vinegar to salt out and ended up with a pink lemonade liquid. I then added lime water and it turned purple. I pulled with the same heptane that I used earlier so IDK which of the pulls worked. I froze and it produced some nice looking very white crystals
Quoting here to ensure this report of positive results gets acknowledged. Of course there was no reason why the process shouldn't work; would you say that the EA/lime/SC process showed any advantage over EA and lime alone, or is it superfluous in the addition of SC? Have you obtained such nice crystals with an EA/lime process?
 
I've not tried lime and ethyl acetate alone. From my understanding you shouldn't mix EA with lye since it'll break down to ethanol. But this has not been observed by me when mixing with sodium carbonate and calcium hydroxide. Maybe the calcium carbonate is a buffer preventing the hydrolysis of the EA?

The nice crystals were from the heptane pulls on the vinegar that was salted from the EA. So results are skewed a bit. I'm sure I had very poor yield but mainly from my own errors.


BTW the heptane did get a little brown color at first but once it settles a bit and is pulled; it returns very clear with that 'white' waves from being saturated.
 
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