Cleaning harmalas with canola oil. Results-->White

[gibran2]

Sorry to hear that you are not getting good results. Maybe it does not work so well with soybean and olive oil.

@ Dagger – are you sure the white powder is freebase alkaloid? How did you basify the vinegar solution? Is it possible the powder is a salt of some sort? Did you try dissolving it in water?

Pretty sure. I used lye to basify the vinegar solution. I dissolved it in water and as expected, it went into solution.


Here are some more pictures. The first is after moving 1 gram of harmine over into the water layer. The second is after freebasing(~650ml water).

In your first photo, is the liquid all vinegar, or is it diluted? You said in one of your posts that you used 35% acetic acid rather than vinegar. Have you tried the technique with vinegar? (Vinegar is typically 5% acetic acid.) Maybe a highly acidic environment is needed to pull alkaloids from the oil?

Also, have you tried any other oils yet? The process seems straightforward, so I’m thinking it has to be either the oil, the acid, or maybe the heating.

How did you heat the oil, and for how long? (I heated mine directly on an electric stovetop, stirring constantly with my thermometer. I’d periodically remove it from heat to ensure the temperature never went above the recommended temp. I heated and stirred for maybe 5 minutes. Maybe not long enough?)

Your second photo looks absolutely beautiful. If only I could get similar results.

 

[gibran2]

Sorry to hear that you are not getting good results. Maybe it does not work so well with soybean and olive oil.

@ Dagger – are you sure the white powder is freebase alkaloid? How did you basify the vinegar solution? Is it possible the powder is a salt of some sort? Did you try dissolving it in water?

Pretty sure. I used lye to basify the vinegar solution. I dissolved it in water and as expected, it went into solution.

Wait a minute – I just re-read your post and noticed you say that your alkaloids dissolved in water? Unless the water is slightly acidic, harmaloids should not dissolve.

Harmine is insoluble in pH neutral water, harmaline is very slightly soluble, and I think (not sure) that THH is also very slightly soluble. The alkaloids should NOT dissolve.

If they dissolved completely, and if your water isn’t acidic, then the alkaloids aren’t harmaloids. Hmm…

(Is it possible you've extracted sodium acetate? edit - Can't be. Sodium acetate is much too soluble to precipitate in the volume of water used.)

 

[prottel]

Wait a minute – I just re-read your post and noticed you say that your alkaloids dissolved in water? Unless the water is slightly acidic, harmaloids should not dissolve.

I added acetic acid, so it was acidic.

In your first photo, is the liquid all vinegar, or is it diluted?

The liquid lower part is water with 2ml 35% acetic acid. The harmine has already moved over into this layer in the picture. It is vinegar I am using, only it is a vinegar essence. A highly acidic ph isn't needed as far as I can tell. pH is not below 5. To put it another way. I used about twice the amount of vinegar that is needed to dissolve 1 gram of harmine.

Also, have you tried any other oils yet? The process seems straightforward, so I’m thinking it has to be either the oil, the acid, or maybe the heating.

I have not extracted with other oils. Only tested if harmine would dissolve. All the oils I tested dissolved it. Wasn't that big a difference.

How did you heat the oil, and for how long? (I heated mine directly on an electric stovetop, stirring constantly with my thermometer. I’d periodically remove it from heat to ensure the temperature never went above the recommended temp. I heated and stirred for maybe 5 minutes. Maybe not long enough?)

I put it inside an oven. It stayed there for about 2 hours, or however long was needed to get a clear solution.

 

[SnozzleBerry]

Interesting...I tried to dissolve some fairly clean alkaloids extracted from rue in canola oil with no success. I used 200mg of alkaloids and 60ml of canola oil, put it in the oven at 150 for a couple of hours, but even after that there were still particles floating around in the oil...any thoughts?

 

[gibran2]

Interesting...I tried to dissolve some fairly clean alkaloids extracted from rue in canola oil with no success. I used 200mg of alkaloids and 60ml of canola oil, put it in the oven at 150 for a couple of hours, but even after that there were still particles floating around in the oil...any thoughts?

ºC or ºF? 150ºC = 300ºF (approx.)

 

[prottel]

150ºC

Interesting...I tried to dissolve some fairly clean alkaloids extracted from rue in canola oil with no success. I used 200mg of alkaloids and 60ml of canola oil, put it in the oven at 150 for a couple of hours, but even after that there were still particles floating around in the oil...any thoughts?

As mentioned above, if you kept 150f then I can understand that there was particles floating around. If you kept 150C, then I don't know. Maybe impurities?

The test I did with rue seeds were fairly clean to begin with. Have not tried dirty rue extract.

 

[SnozzleBerry]

Interesting...I tried to dissolve some fairly clean alkaloids extracted from rue in canola oil with no success. I used 200mg of alkaloids and 60ml of canola oil, put it in the oven at 150 for a couple of hours, but even after that there were still particles floating around in the oil...any thoughts?

ºC or ºF? 150ºC = 300ºF (approx.)

***Facepalm***

Oh boy...looks like the lack of sleep is getting to me...well, as I hadn't seen that I missed the whole farenheit/celsius thing , I took the canola oil/harmala mix and dropped it in my sep funnel, along with a bunch of vinegar. I proceeded to shake the crap outta the funnel until I had a complete emulsion, with no discernible layers. At that point I allowed the layers to separate and drained out the vinegar. I basified about 3 minutes ago; the entire solution went chalk white and from what I can see of the submerged precipitate so far, it seems to have rendered a similar product to dagger's.

Now I'll go try again with the oven at 150C, :lol:

EDIT: Just collected the precipitate...success! :d Product appears to be nearly identical to Dagger's, will confirm once dry.

 

[gibran2]

Interesting...I tried to dissolve some fairly clean alkaloids extracted from rue in canola oil with no success. I used 200mg of alkaloids and 60ml of canola oil, put it in the oven at 150 for a couple of hours, but even after that there were still particles floating around in the oil...any thoughts?

ºC or ºF? 150ºC = 300ºF (approx.)

***Facepalm***

Oh boy...looks like the lack of sleep is getting to me...well, as I hadn't seen that I missed the whole farenheit/celsius thing , I took the canola oil/harmala mix and dropped it in my sep funnel, along with a bunch of vinegar. I proceeded to shake the crap outta the funnel until I had a complete emulsion, with no discernible layers. At that point I allowed the layers to separate and drained out the vinegar. I basified about 3 minutes ago; the entire solution went chalk white and from what I can see of the submerged precipitate so far, it seems to have rendered a similar product to dagger's.

Now I'll go try again with the oven at 150C, :lol:

EDIT: Just collected the precipitate...success! :d Product appears to be nearly identical to Dagger's, will confirm once dry.

So maybe canola oil is necessary for this to work?

 

[prottel]

EDIT: Just collected the precipitate...success! :d Product appears to be nearly identical to Dagger's, will confirm once dry.

Great! Nice to see some others getting good results. Looking forward to the final results.

A separatory funnel would have come in very handy for this step!

Actually, I just tested a mixture of canola oil and water, at somewhat below room temperature. It turns out that canola oil has a hard time moving through a coffee filter, so it should work for separating the water from the oil.

Maybe you should try out canola oil gibran. It may be that it is better at getting a good clean product. Then if you get it working, further experiments could be done with other oils to see if there is any difference.

 

[Crystalito]

Ah ,just a suggestion : DIY phase seperation filters might help further.

(unfortunately i cannot embed it here ,if a mod can please feel free to do)

 

[narmz]

Ah ,just a suggestion : DIY phase seperation filters might help further.

(unfortunately i cannot embed it here ,if a mod can please feel free to do)

Those would be useful if the oil was more dense than water, so things like dichloromethane or chloroform which are immiscible but also more dense and settle below the water later, you are able to separate with these. Because oil floats on top of water, the water will always be in contact with the filter papers and will not let anything through.

 

[gibran2]

Maybe you should try out canola oil gibran. It may be that it is better at getting a good clean product. Then if you get it working, further experiments could be done with other oils to see if there is any difference.

Yes, I'll add canola oil to my next shopping list and try again. I'm also thinking that heating slowly and maintaining the oil at 150ºC for 2 hours in an oven might be a factor (2 hours in an oven vs. 5 minutes on the stovetop).

I'll post my results after I try again.

 

[narmz]

Someone tell me i'm wrong here if I am - could you not just use the canola as a defat step when you have the harmalas in salt form, the harmalas shouldn't dissolve in the canola, but the brown/yellow impurities should - at least according to what I've read of this thread so far. So then you just separate the water layer after defatting and base without having to worry about trying to dissolve the freebase in the canola oil or getting it to migrate back into the water layer - does this not seem easier?

 

[Mindlusion]

Someone tell me i'm wrong here if I am - could you not just use the canola as a defat step when you have the harmalas in salt form, the harmalas shouldn't dissolve in the canola, but the brown/yellow impurities should - at least according to what I've read of this thread so far. So then you just separate the water layer after defatting and base without having to worry about trying to dissolve the freebase in the canola oil or getting it to migrate back into the water layer - does this not seem easier?

Hmm, you could try it narmz, It shouldn't do any harm at least even if it doesn't work.
I might try that on my next extraction.

 

[Crystalito]

Indeed Narmz, i wonder though if from the sides the oil could filter...still i can see the potential problem with solvents less dense than water.

Also,something that sprung to mind: what is the solubility of freebase "harmalas" in naptha/hexane? Could it be used to clean up the harmala alkaloids in the same fashion as canola is used? Or if they are not soluble i wonder if naptha could "decolor" the alkaloids by removing impurities.

 

[Mydriasis]

I've tested the solubility of freebase harmalas in naptha, it is minimal at best(I would say insoluble though it could be very very slightly soluble). Naptha can be used to help defat. It doesn't completely remove all fats from a syrian rue extraction or anything but it can help.

I started a thread with a few solubilities for these compounds. If anyone else does any tests they should add on to it.

 

[prottel]

Someone tell me i'm wrong here if I am - could you not just use the canola as a defat step when you have the harmalas in salt form, the harmalas shouldn't dissolve in the canola, but the brown/yellow impurities should - at least according to what I've read of this thread so far. So then you just separate the water layer after defatting and base without having to worry about trying to dissolve the freebase in the canola oil or getting it to migrate back into the water layer - does this not seem easier?

I tried that. The impurities won't move from the water layer over into the oil layer.

 

[SnozzleBerry]

Someone tell me i'm wrong here if I am - could you not just use the canola as a defat step when you have the harmalas in salt form, the harmalas shouldn't dissolve in the canola, but the brown/yellow impurities should - at least according to what I've read of this thread so far. So then you just separate the water layer after defatting and base without having to worry about trying to dissolve the freebase in the canola oil or getting it to migrate back into the water layer - does this not seem easier?

I tried that. The impurities won't move from the water layer over into the oil layer.

This echoes my experience...I was apparently somewhat hasty in my conclusion that I had reached Dagger's purity with my first extraction (which essentially tried this). The alkaloids were somewhat lighter than they started...from light light tan, so somewhat off-white...but once dried, they were not the brilliant white of dagger's.

Last night I began to heat more oil/harmalas, but there seems to be difficulty dissolving all of it. The oil has begun to take on the same color as in the picture dagger uploaded and I will resume heating/dissolving tonight and post whatever results as soon as I have them. Perhaps a cacnola defat would work if the haramals were in salt form and the oil was already heated to ~300c? I dunno, just a thought.

 

[prottel]

I was apparently somewhat hasty in my conclusion that I had reached Dagger's purity with my first extraction (which essentially tried this). The alkaloids were somewhat lighter than they started...from light light tan, so somewhat off-white...but once dried, they were not the brilliant white of dagger's.

The picture I posted was from caapi. It seems like it is much better at getting a pure white product compared to rue. But this method seems to be much better at cleaning the rue alkaloids than water precipitation is. Just look at the color of the oil after the particles has dissolved. You can do many cleaning steps with water precipitation, but it is difficult to get it to this kind of purity.

Last night I began to heat more oil/harmalas, but there seems to be difficulty dissolving all of it

I haven't had any problems with it. Yes, there are some actives still on the bottom, but that is mainly because I have not managed to make it into finer particles. But the amount is negligible.

SnozzleBerry, when you shook your sep funnel, was the oil still hot? I have been thinking that maybe less impurities would move over into the water layer if the oil and water was colder.

Perhaps a cacnola defat would work if the haramals were in salt form and the oil was already heated to ~300c? I dunno, just a thought.

Maybe, but you can't have any water in it. That would make a boom for sure!

 

[SnozzleBerry]

SnozzleBerry, when you shook your sep funnel, was the oil still hot? I have been thinking that maybe less impurities would move over into the water layer if the oil and water was colder.

No, I've been doing it when the oil had cooled...should it still be hot? If so, how much time should I let it cool after the oven? I just tried again, heated the oil up, it turned that deep deep red, let it cool and salted out, but I don't think my product is that white, it's currently drying...I'll post again. I'll definitely give it another go if you say your oil was hot when you salted out, just let me know.