Is Caapi Extraction as Easy as it Seems?

[gibran2]

I prepared a brew yesterday using 30g of black caapi and tried it last night. I acidified it with fumaric acid, so it ended up being much too sour. I only used half of it, and not wanting to throw away what was left, I figured I’d try to extract the alkaloids. Here’s what I did:

I added a small amount of NaOH to about 50mL of water, then added this to the remaining brew (about 125mL). The brew changed color (went from amber to brown), and in a short amount of time, a brown sediment settled. The liquid portion was dark brown and, since the solids settled, relatively clear. I removed and discarded the liquid. I added about 200mL fresh water, mixed, allowed to settle, and removed the liquid again. I repeated this twice more, at which point the sediment was a pale brown/tan color.

I assumed that the brown color was due to insoluble impurities, so I added about 50mL vinegar to the sediment. After settling, I was left with a yellow solution and a small amount of brown sediment. I removed the liquid to another container and discarded the sediment.

I made more NaOH solution as before, added it to the yellow liquid, and immediately a large amount of off-white precipitate formed. The precipitate rapidly settled (see attached photo). I plan on removing the liquid and adding water to rinse any remaining impurities (including NaOH). I assume I’ll be left with freebase harmalas.

Observations and Questions

What exactly have I extracted? I’m assuming harmine and harmaline, but might I have THH in there as well?

I intend to dry the product, and I’ll report back on the yield, but it seems like a lot – I only used about 15g of caapi.

The product already looks very pure. Why isn’t this method used more often?

Can harmalas from Syrian Rue be extracted using a similar method?

(If there’s already a TEK out there that is similar, I apologize for being too lazy to look it up. )

 

[Crystalito]

If i follow this correctly, then what you have extracted are beta-carbolines, namely harmine, THH and little to none harmaline if the bibliography is correct about caapi.

I think Director of Sound as well as others (sorry, cannot remember usernames right now) have started with a basification, at least for peganum harmala instead of going for a "manske". I remember seeing it couple of times... Thing is , it seems that peganum harmala is more burdensome, due to filtering issues, its as if it contains some sort of resin/gum that clogs filters. It might also contain other impurities that precipitate easier than whats in caapi, at least in my experience there seems to be "something" following the harmalas around during manske and basification although i have to admit i filter coarsely ( i do not grind seeds though).

From a contamination point of view you might have lingering around sodium acetate and sodium fumarate, excluding compounds of plant origin and NaOH. Both of them are soluble in water from what i see online, and quite harmless so no need to worry about them. NaOH leftovers would be my main worry but this can be taken care of, either by neutralising or by washing more with water (here, slight solubility of the freebase in water might account for drop in yield, but i do not have any numbers unfortunatelly, consider it very small though).

 

[endlessness]

yeah if I understand, you're doing an A/B without non-polar solvents, just repeating the A/B steps and letting harmalas precipitate (and filtering/decanting between steps to remove impurities). Sure it should work and theoretically all your harmalas (including THH if there's any in the first place) should be there.

People dont do it with syrian rue because unlike caapi, rue has other unwanted alkaloids, vasicine and vasicinone, which are removed by the manske salt-precipitation step. So one has to do at least one manske if one wants clean harmalas, in the case of rue

 

[gibran2]

yeah if I understand, you're doing an A/B without non-polar solvents, just repeating the A/B steps and letting harmalas precipitate (and filtering/decanting between steps to remove impurities). Sure it should work and theoretically all your harmalas (including THH if there's any in the first place) should be there.

People dont do it with syrian rue because unlike caapi, rue has other unwanted alkaloids, vasicine and vasicinone, which are removed by the manske salt-precipitation step. So one has to do at least one manske if one wants clean harmalas, in the case of rue

Thanks for reminding me about the unwanted alkaloids in rue – I knew there was a reason that the Manske TEK was done on rue.

I dried my product and got a final yield of 323mg – about 2.15%.

To remove the water-soluble impurities, including NaOH, I did 4 water rinses, removing about 95% of the water each time. This means 5% impurities remain after each rinse, so after 4 rinses, 0.000625% remains. Since I added only a gram or 2 of NaOH, after 4 rinses there should be less than 10 micrograms NaOH remaining in a yield of 323mg.


(This also makes me wonder if a similar technique could be used on MHRB? If the MHRB “tea” is dilute enough, the DMT might cleanly precipitate out? Maybe I’ll try it.)

 

[sigmundfreuid]

Please let us know when you will bioassay this,swim is very interested in a report.

 

[olympus mon]

gibran2- do you think this method would work and be an accurate measure of the differences in alkaloids contents between decanted cappi tea vs, its sediment.

ive had a test sample separated sealed and ready to test out but i haven't known of an easy method.

thank you for posting all this. its the first thread in long time that's got me excited with ideas and potential learning opportunity's.

 

[gibran2]

gibran2- do you think this method would work and be an accurate measure of the differences in alkaloids contents between decanted cappi tea vs, its sediment.

ive had a test sample separated sealed and ready to test out but i haven't known of an easy method.

thank you for posting all this. its the first thread in long time that's got me excited with ideas and potential learning opportunity's.

If you can separate the sediment from the decanted tea (I’ve read that freeze/thaw does this?) you can extract them separately and get a rough idea of where the alkaloids are. Good idea!

 

[Malaclypse]

gibran2- do you think this method would work and be an accurate measure of the differences in alkaloids contents between decanted cappi tea vs, its sediment.

ive had a test sample separated sealed and ready to test out but i haven't known of an easy method.

thank you for posting all this. its the first thread in long time that's got me excited with ideas and potential learning opportunity's.

If you can separate the sediment from the decanted tea (I’ve read that freeze/thaw does this?) you can extract them separately and get a rough idea of where the alkaloids are. Good idea!

Yeah, it's not too hard to get the sediment separated with fridge/feeze decanting. You might have a tiny bit of brew left over by trying not to get any of the sediment when decanting, but it should still be very informative when comparing results of this tech between the two.

SWIM would certainly be willing to do a test on his next brew, would be great to have many data sets. He doesn't want to work with NaOH, though. Anyone know if Ca(OH)2 would work?

Also, interested in the bio-assay. Please update when it has been tested.

 

[gibran2]

...SWIM would certainly be willing to do a test on his next brew, would be great to have many data sets. He doesn't want to work with NaOH, though. Anyone know if Ca(OH)2 would work?

Also, interested in the bio-assay. Please update when it has been tested.

I don’t know if calcium hydroxide would work, but when using sodium hydroxide very little is actually used – maybe 5g at most for a 50g caapi extraction. The goal is to neutralize the acid and bring the pH up high enough to just precipitate the alkaloids. (It’s not like a STB where you’re adding 50g NaOH to 750ml water!) Anyhow, give Ca(OH)2 a try!

As far as the bio-assay goes, I’m thinking of taking 225mg of the extracted alkaloids dissolved in a bit of OJ, followed maybe 15 minutes later with about 25mg DMT in OJ. Does this sound about right?

 

[sigmundfreuid]

Or you could try smoking/vaping some...

 

[alzabo]

As far as the bio-assay goes, I’m thinking of taking 225mg of the extracted alkaloids dissolved in a bit of OJ, followed maybe 15 minutes later with about 25mg DMT in OJ. Does this sound about right?

Is that 25mg DMT a salt or freebase?

 

[gibran2]

As far as the bio-assay goes, I’m thinking of taking 225mg of the extracted alkaloids dissolved in a bit of OJ, followed maybe 15 minutes later with about 25mg DMT in OJ. Does this sound about right?

Is that 25mg DMT a salt or freebase?

Freebase harmalas, freebase DMT.

 

[clouds]

rue has other unwanted alkaloids, vasicine and vasicinone, which are removed by the manske salt-precipitation step.

what do you mean by unwanted?

 

[SnozzleBerry]

rue has other unwanted alkaloids, vasicine and vasicinone, which are removed by the manske salt-precipitation step.

what do you mean by unwanted?

Toxic or simply not the alkaloids desired...if you're focused on extracting only Harmine, Harmaline or THH, then any other alkaloids qualify as "unwanted".

 

[clouds]

Toxic

So is rue toxic?

edit: I see. Thanks SB and endlessness.

 

[SnozzleBerry]

rue has other unwanted alkaloids, vasicine and vasicinone, which are removed by the manske salt-precipitation step.

Clouds, both of these alkaloids are toxic afaik, so...yes?

 

[endlessness]

Clouds, unwanted as in, not displaying MAOI activity and having certain health issues. I made a thread about them, check it out: Vasicine Vasicinone and Deoxyvasicine

would be good to get more info for that thread.

 

[ouro]

I believe making a tea, then basing will precip more than just alkaloids. This method is used a lot in the ibogaine literature, and its common for the base precip to be pulled into acetone, which the freebase alks are freely soluble in, leaving behind plant matter. I wonder are freebase harmalas soluble in acetone? Maybe pulling the base precip into acetone and evapping could bring the purity up, or at least test that all the stuff that precips is in fact semi pure alkaloid salts.

side note: this base precip procedure is also how a lot of people are making their home cooked "ormus" from sea salt solution. I've been pretty surprised recently how much stuff falls out of solution at ph > 10... certainly not just alkaloids, and I wonder what it is. Maybe someone with more chem backround can give it a good guess.

 

[gibran2]

I believe making a tea, then basing will precip more than just alkaloids. This method is used a lot in the ibogaine literature, and its common for the base precip to be pulled into acetone, which the freebase alks are freely soluble in, leaving behind plant matter. I wonder are freebase harmalas soluble in acetone? Maybe pulling the base precip into acetone and evapping could bring the purity up, or at least test that all the stuff that precips is in fact semi pure alkaloid salts.

...

The initial basification will precipitate out alkaloids and pull other insoluble solids out as well. The precipitate is repeatedly washed – the wash water is decanted off and discarded. During this process, the pH approaches neutral.

After the precipitate is fairly clean, it is acidified. All insoluble material is allowed to settle (mostly plant particles/dust). The clear yellow solution is decanted and saved, the brownish precipitate is discarded.

At this point I assume the solution contains only alkaloids (and I suppose any other substances insoluble at pH>7, soluble at pH<7). The solution is basified a second time (this time just to get the alkaloids in freebase form), the off-white precipitate is rinsed repeatedly (with a resultant lowering of pH – approaching neutral), and air-dried.

 

[ouro]

Yeah, your right that could get rid of the mystery precip. I sort of assumed that if some plant material was in solution, but precipped in basic solution, it would be soluble in acid, even though some stuff clearly doesn't make it into the acid solution. My chem isnt good enough to really understand that kind of conditional solubility. Still, I wonder if the FB harmalas are soluble in acetone.. it could be a good way to clean/purify further.