I was just wondering if we could get a few pointers together for harmala extractions.
I'm finding their relatively low solubility in naptha to be a pain, and the manske technique
is not of much help because of a dense, muddy solution. With filtering the solution became
clear, but SWIM aborted extraction because he was loosing product after a couple of cotton
balls clogged up with salt and sediment.

Obviously, Im no expert. Im gonna go re-think this approach. I really wish there was some
readilly available solvent which would grab this stuff easilly, like an acetone drytek or something.
ground seeds + acetone, soak -> evap -> harmalas.

Harmine and harmaline have xlogp3 values of 1.2 and 3.6 respectively. So pulling both at once is a problem, or maybe is to our advantage.

I *guess* anything with xLogP3 value of 3 and higher should pull harmaline - naptha, D-Limonene. and again i *suppose* harmine can be pulled with acetone, but i think Isopropyl alcohol will pull it better. I'm basing this entirely on endlessness' xlogp solubility thread.

Shoe, how are you pulling with naptha? Do you just grind seeds, cover with water and add naptha?

no, first its an acidic boil with vinegar and water, then that is basified and naptha added. this yeilded very little harmalas, so don't bother.

Shoe, one project I wanted to do try with harmalas is pulling with limonene after freebasing the acqueous solution with them. The thing is, it might be that limonene also pulls vasicine and vasicinone, im not sure. I still have to add them to the psychedelic compounds properties wiki, but pubchem says vasicine's and vasinone's xlogp3 is 0.4... I dont know if they are or not soluble in limo.

A manske would for sure get rid of them, so I was thinking maybe after having been salted out of lemonene with vinegar, there would be much less impurities and therefore the manske result would be much easier to filter. Then one redissolve, freebase and filter to achieve hopefully pure harmalas, bypassing the annoying filtering when there's too much impurities.

If you want to try, I would be glad to read the results... Otherwise in a month or two I will definitely do these tests

Im sorry but Im not at all for this manske technique... It absoloutely sucks. Waiting for cloudy bits to preciptiate out, then collecting them and drying them out? eating 50% salt and 50% harmalines? no. sorry, its crystal or no deal.

I dont think you understood what I said. Youre not eating salt, you redissolve the manske precipitates and freebase, so there is no salt contamination, only precipitated freebase harmalas. The manske is only an intermediate step for removing vasicine and vasicinone, which is a question you didnt consider in your post.. So what about them?

im not concerned. If its in rue, its fine by swim.

What do the freebased harmalas do then, since they will seek the np layer, which there isn't....
They precipitate then, im guessing? That wasn't in any of the teks I read!! lol

A speedier harmala extraction would be most tubular and rad.
I'm sure if we all pool our notes, we can come up with some good insights.

Here's my current process. It's mostly the same process as on the wiki plus I tweaked it in order to reduce time spent filtering.

1.) Grind the rue and spoon the powder into teabags.

2.) Simmer for a while in either ph neutral or acidic water for somewhere between 20min and 120min.
Drain the solution into a collection vessel.
Rinse the teabags in hot water a few times and combine into the collection vessel.

3.) Strain solution through a gold filter, t-shirt, cheese-cloth, sort of thing. This should only take a minute.

4.) Reduce solution on stove top. The less liquid the better but there needs to be enough water that the harmalas don't drop out of solution and stick to the pot. I'm thinking like 200-500ml of water if extracting from 100g of seeds should be sufficient. Perhaps after several trials, a sweet spot can be determined.

5.) Strain again through gold filter to remove the crud that builds up after reducing.

6.) Add the now filtered and reduced solution to a large amount of hot salt saturated water. The water must be acidic or ph neutral. 500ml salt saturated water worked well when extracting from 100g of seeds.
*Instantly a precipitate forms as a sparkling mass of tiny crystals.*
Stir it with a chopstick for a couple minutes.

7.) Filter while still hot through a gold filter, etc. Again, this should only take a minute.
You can discard the liquid now or filter through a paper filter for a greater yield.

8.) Rinse the harmalas out of your filter using a minimum amount of hot ph neutral water. Collect the solution.

9.) Add your harmala containing solution to a large amount of hot sodium carbonate saturated water.
*Instantly a precipitate forms as a sparkling mass of tiny crystals.*
Stir with a chopstick for a minute.

10.) Filter while still hot through a gold filter, etc. Once more, this should only take a minute.
You can discard the liquid now or filter through a paper filter for a greater yield.

11.) While the harmalas are still in the filter, rinse with ph neutral water.
This will remove excess sodium carbonate. *I haven't actually tried this step.

12.) If freebase harmalas are your goal, rinse the harmalas out of the filter using ph neutral water (or your solvent of choice) and let dry. Otherwise, proceed with this recipe.

13.) Use a minimum of hot acidic water to rinse the harmalas out of the filter and stir until fully dissolved, adding more liquid if necessary.
Let them dry or keep liquid for tincture.
*If you use vinegar to acidify the water, and evaporate, all the excess acetic acid will evaporate. Otherwise there may be contamination present from a non-volatile acid.

That's it in a nutshell. Next time I do this, I'll take a stopwatch and record my time on each step. If any one else wanted to do the same, we could compare times and that would be cool.

Great Tek Alzabo, I'll try this one. But just just note that other members have different skins installed; mine is mostly white and light blue and so your colours make it almost unreadable - I had to copy + paste the text into notepad. My advice is just to leave the colours as default.

Here you go

There are few non-water solvents that will dissolve efficiently and pull freebased harmalas. SWIM has tried methanol, ethanol, acetone, and xylene and neither was good enough. Nothing compared to, say dmt where a splash of acetone or xylene dissolves it nicely.

DCM does the job nicely however, and along with its cousin chloroform they are the preferred NP solvents for pulling harmalas out of aqueous solutions.

I also tried with IPA and it was neither very good (for freebase harmalas).. So I guess limonene wont pull it too well either, but maybe enough to be worth using it, if it could indeed help with avoiding the worse part of filtering.

Some additional thoughts;

For higher yield,
After each precipitation step, once the bulk of the solids have been collected,
place the liquid in a fridge overnight to allow more solids to precipitate.

For a very clean product, there may be an easier way than multiple precipitation steps.
My feeling is that 1 salt and 1 sodium carbonate steps are sufficient.

One can use a large amount of salt saturated water and a large amount of sodium carbonate saturated water.
For example, in the manske step,
add your reduced and filtered rue tea to 5 gallons of hot salt saturated water and stir with a whisk.
This should allow the bulk of impurities to dissolve.
The same can be done for the base step.

OR after the base step, collect the harmalas and wrap them in a couple coffee filters,
secure with rubber bands and let steep in hot distilled water, changing the water until it runs clear.

I like the latter approach more as it doesn't call for excessive amounts of salt or sodium carbonate and should also wash away any impurities of sodium carbonate from the end product.

What's the melting temp of freebase harmalas?
I'm wondering if there's any reason the freebase harmala teabags shouldn't be simmered in distilled water.

Did you ever do any of this that you're saying, or is it theoretical?

For example when you say:

"My feeling is that 1 salt and 1 sodium carbonate steps are sufficient.", what do you mean? I have tried this and the product was dark tan or dark brown. It was of course active, but dosage wasnt as accurate because of impurities (I needed 1.5-2x more of it for same effects as pure white ones). So yeah, its sufficient in a way but then again it all depends what one wants, just an active product regardless of looks and purity, or if they want a much purer product (with some yield loss).

I dont understand what you mean with this:



why would the large amounts of water help, do you suppose? At least in the sodium carbonate step it would be counter-productive. Harmaline freebase is slightly soluble in water so the more water you use (and the same for the idea of 'washing it with water to remove impurities", the more harmaline you will lose.

As for the melting point and other alkaloid data, check here

I didn't realize there was a solubility issue.
That means that repeatedly washing the freebase harmalas in distilled water would lose a significant quantity of harmaline.
I thought the idea had merit, I guess not though .
I haven't tried the washing step or the large amount of saturated solution step yet.
I was speculating about more efficient ways to clean out impurities.
My idea with using more salt water in the single manske step was that there would be more solvent for the impurities to go into but the harmalas would remain insoluble -- impurities get diluted and goodies get concentrated.
That's my theory at least. I haven't tried it like that, I should have been more clear in my last post.

Ok, so here's another idea;
After the manske step, collect the harmalas and wrap in several coffee filters. Add these filters to a pot of hot salt saturated water and let steep, changing the water periodically until it runs clear.

^this should have the same effect as multiple manske steps without filtering multiple times, yes?

Also, what's with these numbers for harmaline?
Why is the melting point higher than the boiling point?

Freebase Harmaline

* Melting point: 232-234 °C (Sigma Aldrich)
* Boiling point: 120-140 °C at 0.001 mm/Hg (TIHKAL)

Plus freebase harmine has no boiling point?

Freebase Harmine

* Melting point: 262-264 °C (Sigma Aldrich)
* Boiling point: ???

you could try the harmala coffee filter clean up, I would be curious on the results

as for the melting point, note that the melting point is not exactly higher than the boiling point.. The detail is in the pressure. At lower pressure, the boiling point lowers, and 0.001 mm/Hg is a very low pressure. So in normal atmospheric pressure it is for sure significantly higher.

As for why no boiling point for harmine, simply because the searches in published literature did not reveal any information regarding boiling point. Maybe nobody tested, maybe we just werent thorough enough in our searches. If you can find this information from trustable source, feel free to edit the wiki and post the source

Awsome!

I will try this just as soon as I dock with the mothership.
Right now, there are jellyfish to dance with.

*puts on space goggles and zoomz away*

Why crystal or no deal?

I'm just that kind of guy

I wrapped some sparkly dirt in coffee filters and let steep in hot water overnight.
The harmalas still looked like sparkly dirt in the morning.

Although this method proved ineffective this time, it may be a matter of technique.
I will try again next time I process some seeds.