Someone on eBay is selling harmine/harmaline cheap.

2) SWIM was thinking of using the acetone route to get the alkaloids out of the plant material in a salt form and convert them into fumarate salts, as with the DMT.

1) He doesn't know if it would work with citric acid as most syrian rue extraction TEKs use acetic acid, that's why he assumed that anhydrous acetic acid might work better with the acetone. Of course he doesn't know if acetic acid is soluble in acetone.
(If SWIM understands correctly, in A/B extractions the Acid phase pulls out the alkaloids into the water from the plant material, and the Base phase converts them back into freebase, so they can be pulled out with solvent of choice?)

SWIM may better ask than presume:
Is it possible to us the FASA Tek to extract the alkaloids from Syrian Rue?

Yes, to some extend but it is not the best route available.

One reason is the not so great solubility of harmalas in xylene (but still fine if one fancies doing 20 or so pulls)

The other is a more serious one; SWIM has done FASA on harmalas, basically dissolving the crude freebases from p.harmala in acetone, then precipitated the alkaloids with FASA. It works, and one can see beautiful yellow precipitates, but if they are left for too long (i.e. an hour or so) in the acetone mixture they will start turning red. The nature of the harmalas-turned-red alkaloids is unclear, so is their bioactivity. Some people have tested the harmalas-turned-red alkaloids (crated by a different route however) and have found them to be inactive. SWIM believes that there is something not very good done to harmala alkaloids when they turn red.

What the red is or how it is formed is a matter of speculation.

Finally, citric acid does not go well with Manske prcipitation. SWIM has tried that. Beter stick with the standard store-bought vinegar

There’s nothing magical about acetic acid. All the acids work that SWIM tried.

Citric acid works just as well as acetic acid for the Manske method in terms of final yield, but it takes LONGER. Acetates are much quicker to convert to hydrochlorides than citrates are by the action of sodium chloride on harmala alkaloids. SWIM knows, he’s used citric acid many times and the yields are the same, it just takes longer. Something like 2-3 times longer.

True, thanks for pointing that out. When SWIM tried citric acid he did not see precipitation within the expected time. And he did not bothered waiting. He tried to salvage it by dumping a massive amount of HCl in the acid solution to convert the citrates to their hydrochloride salts (or so he thought, hahahaha). It did work at that time.

When SWIM did his harmala extractions manske+base precipitation, he used ammonia as a base. SWIM used only a few drops.

Now he moved and cannot find ammonia anymore. ph of ammonia seems to be 11.6. Is sodium bicarbonate an option, or is it too low ph?

what about sodium carbonate? isnt it possible to make sodium carbonate by putting sodium bicarbonate in a tray in the oven?

how much should SWIM use?

ok so SWIM found sodium carbonate.. Is it or is it not ok to use it instead of ammonia when basifying the acqueous solution to precipitate harmalas freebase? SWIM cant think of any reason why not, but maybe some of you guys know better..

how much should one use of sodium carbonate? I saw somewhere the pH was about 11.. I guess then even if I add too much it wont hurt the harmalas, but maybe it would precipitate/decant together with the harmalas, which I dont want, so how much dissolves in, say, 100ml of water (considering it has harmalas inside) ?

thanks

The only difference is that ammonia will precipitate harmine and harmaline, while sodium carbonate will precipitate harmine, harmaline, and harmalol (if there’s any present).

thanks! and what do we know about harmalol? googling it shows some sort of neuro protective properties, and also that it is a metabolite of harmaline. So I guess it cant be a bad thing..

how well does sodium carbonate dissolve in water? to get the desired pH, will I be near or far from the sodium carbonate saturation level ?

The pH depends on many factors. It's too hard to guess without knowing the quantities.

Sodium carbonate dissolves very well in water. 30 grams dissolves in 100 ml of water (that’s 30%). A 1% solution in water has a pH of 11.5.


Note that harmalol can't be extracted with the Manske method.

Do not worry, it is pretty soluble. Soluble enough to give a pH of 12.

But beware of one thing. Mixing sodium carbonate with acid will liberate carbon dioxide. Just add sodium carbonate in vinegar or lemon juice and see what happens. It's funny, the liquid foams up as the acid is neutralised by the sodium carbonate.

So just be careful when basifying; add slow amounts of sodium carbonate, then wait for the foam to settle (takes less than one minute! then add more. When no more foam forms after Na2CO3 addition, the solution is neutral (pH~7). From this point onwards it is safe to dump in the solution as much sodium carbonate as one desires.

excellent, thanks a lot ron and ..dibulum

btw, SWIM is right now making the extraction with 150g rue.. After making the tea and filtering, the total amount of water he was left with in the end was 3 liters. He then decanted in two jars in the fridge overnight, threw away the solid particles that decanted and put the liquid together. Now he is boiling down so that it all fits in a better container for the salt precipitation part. Is it safe to reduce from 3l to, say, 750ml of tea? Enough water for actives to be safe in solution, in a low-flame boil?

btw one more question. How comes some people pre-saturate a separate solution with salt and then mix the tea with the salt-saturated solution? It never made sense to SWIM, why not just saturate the rue tea with salt straight away? Why bother increasing the amount of water, and anyways the salt in the saturated solution will dilute with the tea, and it might not be enough, so then people add more salt on top.. seems pretty sloppy. SWIM just saturates, like 36g for 100ml as if its pure water, and even if its too much and some salt precipitates, no problem because in the base-adding step, the salt will remain in the solution while only the harmalas precipitate as freebase.

Well IPA works a charm. My friend has been going through suspense as he only had IPA to hand and after 3 days boiling liquids and filtering out what only looked like mud, he now has a nice dark red solution ready for evapping .

You shouldn't use IPA or any other alcohol unless its done without any oxygen present. It causes a red color to form from degradation of the alkaloids. The longer they sit in it, the redder it gets, and the more your alkaloids are converted to harmala red. This is why alcohol is not normally used to extract harmala alkaloids. Its great for making harmala red though, which is why your IPA solution is red.

Acetone seems to also do this.

Hmm... that's no good.

I'm now a little confused about how most harmala teks I've read involve alcohol.

Well several old books document this. Heat makes the red material form even faster. SWIM has seen it happen with IPA and with acetone. It's oxidation of some sort which doesn't easily happen when using water. I don’t know if the harmala red material is active or not. It might be just as active as harmine and harmaline. Currently no one has documented the structure of harmala red. Very little is known about it other than it’s used to dye carpets.

are harmalas soluble in naphtha? does a standard a/b work?

I ask this because SWIM was making manske+basification, but for some reason this one is being specially a pain in the ass to filter. So SWIM just completed the salt precipitation part, redissolved it in more water, but he did not basify it yet.. He wondered if he could basify it, and instead of letting precipitate the freebase and then going through the problem of filtering, he would basify, mix with naphtha, separate naphtha and evaporate... would that work?

Filtering can be extremely tough sometimes. I believe mucilage is responsible for this. Mucilage should break down if cooked for an hour at 250 F.

The Chemical Gazette says harmine is slightly soluble in naphtha, so naphtha would not be a good solvent.

Most A/B extractions I've seen use DCM or chloroform for the harmala alkaloids.

Ok after that little mishap SWIM has dried the lot and he's looking at a mixture of white, palish brown and a little bit of red. It's all pretty mixed up, but does anyone know of a tried and tested method to get the good stuff out?

SWIM's a little frustrated with himself for rushing and not researching more thoroughly. Needless to say next time he'll just filter a hell of a lot more and then basify with NaCO3 rather than disolving in alcohol.

are harmalas soluble in naphtha? does harmala red form when evapping naphtha with harmalas? does freeze precipitation work with harmalas and naphtha?