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Crystalline Caapi Alkaloids

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gibran2

gibran2

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Thanks to Enoon’s accidental discovery that freebase harmala alkaloids crystallize when in a solution containing alcohol, I’ve done a few experiments.

Here’s what I did:

I started with about 530mg of FV’s Caapi Copy (didn’t want to experiment on my good stuff!). I dissolved it in 10ml vinegar, then added 50ml 91% IPA. I dissolved 1g NaOH in 20ml water, then added this to the alkaloid solution. Next, I added 100ml boiling water.

I let the hot solution cool to room temperature undisturbed, and the result was some very nice crystals! I decanted, added water, decanted again twice more, then dried the resultant crystals.

Other than looking all nice and sparkly, I don’t know if there’s any reason to take this extra step, but it sure does look nice!
 

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Wow, nice gibran2!!! Really pretty crystals! Personally I think I will add alcohol/IPA to all my harmala extractions from now on, because a) they're so pretty and b) I found them easier to wash/deal with

cheers & love
Enoon
 
Gibran, was there any yield loss/change from the recrystallization?

I wonder if this would work with syrian rue as well?

I've got a rue extraction in the final stages, so I'll give it a shot in the next day or so and report back.
 
Melodic Catastrophe said:
Gibran, was there any yield loss/change from the recrystallization?

I wonder if this would work with syrian rue as well?

I've got a rue extraction in the final stages, so I'll give it a shot in the next day or so and report back.
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No discernable loss of yield.
 
elru said:
I just read the post in the other thread about the taste. Did you figure out what exactly the crystals are? Have you tried this with sodium carbonate instead of NaOH?
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I’m fairly certain that the crystals are just crystallized caapi alkaloids. I tasted some of my caapi extracted alkaloids and discovered that they’re not bitter either. (The alkaloids I extracted from Syrian Rue had a distinctly bitter taste.)

I haven’t tried doing the extraction with sodium carbonate, but I think others have. I don’t remember the results, but I think they’re posted in the extraction thread.
 
ok, in the last week we got diamond spice crystals and now harmala crystals. Can they be crystallized together?
 
Very nice. What is the purpose of the ipa? I recall your caapi tek just using acid water, then NaOH, then water washes.
 
I repeated my extraction procedure using 400ml of 3% acetic acid and 20-30ml of denatured ethanol from the hardware store (96%?). I also got two layers at first when I added the lye (the top layer was clear and greenish, the bottom layer brown). Then I shook and got some nice, small crystals again. I currently drying in the filter.
Would be nice to find the optimal crystalization-conditions :D
 
Considering denatured alcohol contains substances to make alcohol toxic or taste incredibly bitter so it isnt consumed, arent you worried using that for harmala extraction? What is the denaturing agent in that alcohol?
 
They usually use acetone, MEK or IPA here. Since I'm washing the harmalas I'm not all that worried. Though I would rather use pure EtOH... it's just about 10 times as expensive. Taxes :(
 
elru said:
I just tried this using closer to 10 or 15ml of 91% IPA and 1.6g caapi harmalas and it looks like it's just precipitating out. As I added the lye though it did something kind of weird. When I put in the first couple drops I saw some shiny things in the liquid that looked kind of like fish scales or flakes of glass. I kept adding the lye and as it was all mixing in a layer of white stuff came to the top that looked like creamy snowflakes or curdled milk. They clumped together on top. I added the hot water and they dissolved back into the liquid, which formed layers and the harmalas seem to be precipitating out.
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On trials with IPA, I also had normal precipitation occur if I didn’t add enough alcohol. It seems that with IPA at least, the higher the ratio of alcohol to water, the better.

It might also have to do with the quantity of alkaloids relative to the volume of liquid – too concentrated and it precipitates out prematurely.

By the way – those white snowflakes are very pure alkaloids. I’ve never managed to get them that white!
 
I’m fairly certain that the crystals are just crystallized caapi alkaloids. I tasted some of my caapi extracted alkaloids and discovered that they’re not bitter either. (The alkaloids I extracted from Syrian Rue had a distinctly bitter taste.)
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Did you taste it in its freebase form? As a freebase the harmalas does not have much of a taste, but in its salt form, it tastes distinctly bitter, but has no other taste as long as all the impurities has been removed.
 
elru said:
Oh nice! Once this settles out I'll try repeating it and collecting the snowflakes. Because they are on top rather than on bottom I'm not so sure how to separate them from the liquid without having to slowly filter lye through a coffee filter (something I'm not particularly comfortable with safety-wise). Do you have any ideas for how to collect them?
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Usually they float to the top because air/gas bubbles are trapped in them. Giving them a good stir usually helps them to settle. However, if I had such nice white precipitate floating on top, I’d skim it off with a spoon and rinse it into another container.
 
Dagger said:
I’m fairly certain that the crystals are just crystallized caapi alkaloids. I tasted some of my caapi extracted alkaloids and discovered that they’re not bitter either. (The alkaloids I extracted from Syrian Rue had a distinctly bitter taste.)
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Did you taste it in its freebase form? As a freebase the harmalas does not have much of a taste, but in its salt form, it tastes distinctly bitter, but has no other taste as long as all the impurities has been removed.
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My caapi extracted alkaloids in freebase form are not bitter. I'll have to sample my rue extracted alkaloids again, but I think they were bitter. I'm wondering if freebase harmaline has a bitter taste?
 
gibran2 said:
My caapi extracted alkaloids in freebase form are not bitter. I'll have to sample my rue extracted alkaloids again, but I think they were bitter. I'm wondering if freebase harmaline has a bitter taste?
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Just tested powdered harmaline freebase. Did not taste anything. It is not bitter. If rue extracted alkaloids were bitter, either they were in salt form or there was some kind of contaminant from rue.
 
Dagger said:
gibran2 said:
My caapi extracted alkaloids in freebase form are not bitter. I'll have to sample my rue extracted alkaloids again, but I think they were bitter. I'm wondering if freebase harmaline has a bitter taste?
Click to expand...
Just tested powdered harmaline freebase. Did not taste anything. It is not bitter. If rue extracted alkaloids were bitter, either they were in salt form or there was some kind of contaminant from rue.
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ime, harmalas extracted from rue are always slightly bitter in the fb form
 
Ok, so I just did an A/B cleanup on the liquid that was filtered after salting a rue-tea and got the same crystals that mydriasis was talking about in his thread. These are not the IPA-induced crystals, although, from your pictures, gibran, they look pretty similar.

Does anyone know what might cause this? I haven't filtered them yet, but assuming they are like myd's xtals, I expect them to degrade in quality when I do. I just find this really bizarre. Before I filter, I may make some IPA xtals and see how they compare physically.

I don't understand how the crystals would form this way (not that I truly understand how they form in IPA...buuuuuut...)
 
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