Hi everyone! I recently completed my very first successful extraction of harmalas from Syrian rue, thanks to all the wonderful information this community has made available to the world. I was roughly following the Tao of Rue tek as well as the Easy Caapi Vine tek, both of which are fantastic. But was having difficulty with the washing step as I felt I was losing a fair amount of alkaloids when I would decant off the top.

So, I decided to simply run the freebase harmalas and alkaline solution through a coffee filter. And after the solution went through, I added fresh cold water to the freebase harmalas caught in the filter. I did this 4-5 times until the water came through slightly cloudy but no longer tasted like sodium carbonate. (I know this is not great lab etiquette...)

My question - was this a mistake? Did I lose alkaloids doing it this way? This seemed much easier than waiting for the precipitate to fall to the bottom, which if done correctly might take 5+ hours for 4 washes.

Any thoughts or input from you all would really helpfull.

In bold, italics, and underlined: Lolololol!!! You are right! It's not good lab etiquette, but it's still pretty funny. If this were any kind of extraction that used a solvent like naphtha or xylene - I'd have gotten on to you. Harmalas extractions are pretty safe, unless you decide to use sodium hydroxide instead of sodium carbonate. (Still safe... just "less" safe.)


As far as your method of filtration and washing - you are possibly the first person who has said they'd rather filter than wait! Even when I did filter, I didn't have a filter flask at the time, so it took FOREVER to wait for the coffee filter to drain. Then it would clog halfway through. Then I'd have to play "transfer the contents of one filter to a new one," only to find that the new one clogged 2 minutes and 46 seconds later. I'd imagine this is all based on scaling and how much filtering took place before hand.

Most of my clogs were likely from the seed material.

If I were to extract harmalas now-a-daze, i would brew the seeds, use a metal strainer to get a majority of the seed/plant matter out, then allow the aqueous to rest as the remaining plant matter settles. Once settled, I'd use a siphon to remove the majority of the solution, leaving only the plant matter and a small amount of solution behind, then do a quick filtration on that.

After the aqueous solution has been separated from remaining plant matter, I would put the solution on a magnetic stirrer with a pH probe inserted. I would titrate a base solution, while stirring, until the pH is right at 8. That should be high enoug to precipitate some of the harmine from the solution. I'd allow it to settle, then siphon the solution from the harmine. I'd then return the solution to the magnetic stirrer and titrate base until the pH is roughly 9.5 - that should precipitate most of the remaining harmine and begin to precipitate the harmaline. I'd let that precipitate settle, siphon the aqueous, and then return the aqueous solution to the magnetic stirrer. I'd titrate some acidic solution to drop the pH to 7 and then return the solution to the pot used for initial brewing.

It's been said that extensive heat will convert harmaline into THH. So, I'd let it lightly simmer for a few hours, return to the magnetic stirrer, titrate to a pH of 11 (precipitating most of the remaining harmala alkaloids) and then siphon the aqueous from the precipitate, and begin the cleaning processes.

If you don't care about isolation, then just go straight to a pH of 11. That will knock most of the alks from solution.

When you wash, are you adjusting the pH at all? If not, be sure that you're not using water that is acidic. When washing, it's best to use cold water that has a pH that is near the pKa of the specific alkaloid. Otherwise, if too low, then the wash will convert some of the freebase back to the salt and pull it with the wash. If the pH has not been adjusted for the alkaloid, make sure to get it as cold as possible.


In short, yeah your method can work. As you may suspect, unless the pH is accounted for, then there may be some loss. If the pH was very high to start, then the base used for initial precipitation may be enough to buffer the wash while not over concerning yourself about much loss. Plus, nothing is lost until you pour it out. Even if there is "loss" from a wash (or series of washes), it is retrievable. Just save your washes and check the pH of the wash solution. If it's below 7, then titrate some base. If precipitation forms, you've un-lost your loss.

Personally, I prefer harmine over harmaline. That's why I would go through the extra effort of separation. Most folks are happy with the full blend. Patience is a virtue, not a pain in the ass.

Take Care!
ACY

(Ha. My dad always used to say: you can't be a doctor if you don't have any patients [patience].)

This is too funny... I asked my wife if she would mind bringing me a shirt (was getting out of the shower.)

I hope you appreciate the synchronicity as much as I did.

I want one!!! Where's it from?