ok, I don't know how exactly I managed to make them come out like this, but I'll tell you what I did...

remember that EtOH extraction on caapi I did and only got about .6% yield? Well I decided to try and get the rest of the alkaloids out by soaking the caapi (which was still damp with EtOH) in 3% vinegar as with the cold extraction. I let it sit for about 2 weeks because I was lazy and busy. Today I filtered and based with lye.
I had about 300ml of orange liquid and added 100ml of H2O+9.8g NaOH still slightly warm but clear to the orange liquid. It turned dark brown and then ... this happened:



Any ideas why? Is it the leftover ethanol that is supporting crystal growth?

Any ideas on how I should clean them without breaking them? They're so pretty...

cheers & much love
Enoon

Any ideas how I could clean them without breaking them?

Carefully decant the solution after allowing the crystals to settle. Once left with mostly crystals do some gravity filtration or vacuum filtration. Gently wash perhaps with water. If they break and fall away you can always try to recrystalize them.

I'm not terribly sure about the solvent mixture maybe 1:1 benzene and acetone? It really depends on what those crystals are .

i'm no expert, but I'd say the sodium hydroxide is whats causing that crystal growth, all 9.8g of it.

hehe - seen this before - nice harmaloids - well done.
use an oil filter - and pour slowly - their brittle and will settle like hair on the filter.

And this is what the final result looked like. The crystals are small so you can't see them well in the picture, but it definitely looks different than my usual extract which is more powdery and forms clumps. This formed a rug-like net of fine crystals which are extremely light and I had to hold my breath scraping them up so I wouldn't blow them all over the place.




bringing my yield up to 1.0% ... I just started another round of cold extraction on the same vine to see if there's more left... 400ml of 3% vinegar and a shot (15ml) of ethanol. Let's see if I can reproduce these xtals

cheers and good night

you and me both! The only difference in this extraction to the others is the residual ethanol (methylated/denatured ethanol) in it. So an experiment would be to try adding a small amount of ethanol to a caapi brew and finding out if xtals form when basing. They were really nice to work with, so if ethanol really does it I'm adding some to every caapi extraction from now on

if anyone has the chance to test this, please report back.

OK – I just tested! Here’s what I did:

I dissolved about 200-300mg of caapi alkaloids in a very small amount of vinegar (<5mL). I didn’t have denatured ethanol, so I used 91% isopropanol – I added maybe 40mL.

I then dissolved less than 1g of NaOH in about 20mL of water. I added this to the iso/caapi mix. Nothing happened! No precipitate. So I figured maybe I had too much alcohol – I added about 100mL water to dilute. Still nothing. I tested pH and it was about 12.

I had breakfast, and when I looked at the solution… crystals! They are very small needle-like crystals, maybe 2mm long at most, but very similar to the crystals in the photo.

We need a chemist to tell us why this works.

awesome, thank you so much gibran2 for testing this!!!

So in your case you had 40mL IPA to ~100mL water ? I'm sure I had much less ethanol:water in my solution than that and still crystals.

I agree about the chemist..., I'd love to know how/why this works!

I’m thinking that this might be a good way to get very pure alkaloids. I’m going to re-crystallize several times and see what happens.

Will report back…

One thing that I doubt plays any interaction in this is that-
C2H5OH + NaOH <=> C2H5ONa + H2O

I don't see sodium ethoxide performing a claisen condensation on any of the actives. It is a reducing agent, I think? Wonder if it is strong enough too reduce harmine into harmaline. This would lead to a higher purity of harmaline which would promote crystalline growth.(Or do I have this backwards? damn oxidation/reduction)

I'm not to seasoned with organic chemistry though.Ruled out.

Have you tried a test run with similar conditions using no ethanol or isopropanol? I've gotten crystals, albeit those are nicer ones but the variable should be tested in parallel to compare results.

My assumption is solubility conditions. Perhaps the xtals are more soluble in ethanol/isopropanol(being that their less polar than water). Though still not soluble enough in them to stay in solution especially one that dilute.

Hopefully someone else could elucidate this with real chem. knowledge.

I just tried a 2nd re-crystalization, this time using less isopropyl than before (maybe 20mL to 100mL water), and oddly enough, the solution turned milky white when NaOH was added – as it does when no alcohol is present.

I’ll try a 3rd re-crystallization later today. I think this is a very good way to get very pure harmala alkaloids – the precipitate is almost pure white.

(I’ve never gotten crystals before – just a fine precipitate that that tends to aggregate.)

mmm maybe you do acetate at first than you add alcool that will low the harmas acetates solution..but that is not important swim thinks,anyway..when you put naoh you freebase the alks that will dissolve in the mix that would be a bad solvent for them but it is able to brings the harmalas in solution...when some alcool evaporates,the solvent capacity get lower and release the harmalas as crystals couse they become available free in the solution very very slowly,so they could aggregate in crystals form istead of powder precip.

@ Enoon - Have you tasted your caapi alkaloids yet?

I dried my alkaloid crystals (they look very similar to your dried crystals) and took 20mg sublingually. Oddly enough, there was no bitter flavor. Caapi alkaloids have always been very bitter, but these crystals tasted almost like baking soda – no bitterness at all.

Now I’m wondering what exactly the crystals are?

(I did a stupid thing and mixed the remaining alkaloid crystals with the vial I originally got them from, so I can’t test them further. Doh!)

I'll have to try them when I get home... luckily I didn't mix mine with the rest of my caapi though I was close to doing it... then thought the better of it. I love your pic btw, they look so sparkly!
I have to admit I never thought the harmala taste was bitter, at least not with caapi, as long as I didn't mix it with acid whereby making it a salt. How could we find out what these are? Mass spec?