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Acetic Acid Isolation of Harmine and Harmaline
Mankse's Acetic Acid Peganum Harmala Extraction
by Erowid, et al. per Manske


Take rue, powder it, place it water with small amount of acetic acid (distilled vinager) bring to simmer, cool and strain, repeat at least once, on the last batch, add the strained water hot and dissolve a good quantity of non iodized salt into the water, place in fridge/freezer (watch it so it don't freeze and break your container) and cool down to really cold, brownish orange flakes will percipitate out, let set in fridge until flakes settle to bottom, pour off excess liquid, then filter the rest through a coffee filter, wash with cold salt water, dry and scrape off the powder.

This is extremely efficient and I understand is the technique used in the field to test for harmaline.

From "The Alkaloids" Vol II (p393), Mankse:

"The crushed seeds of Peganum Harmala are covered with three times their weight of water containing 30 g of acetic acid per liter of water [white vinegar is about 50g / l or 5 %]. The seeds swell as they absorb the liquid and form a thick dough which is pressed after 2-3 days. The pressed seeds are once more treated as above with twice their weight of dilute acetic acid and, after maceration, the liquid is again pressed out. To the combined liquors, sodium chloride [that's table salt, man] (100g. / liter of liquid) is added to transform the acetates of harmine and harmaline into the hydrochlorides which are insoluble in cold sodium chloride solutions and are precipitated during cooling. The supernatant liquid is siphoned off, the crystalline residue filtered with suction and redissolved in hot water.

Addition of sodium chloride to the filtered solution causes the precipitation of the hydrochlorides as a crystalline mush and this process is repeated until the hydrochlorides have acquired a yellow color (for the purposes of this newsgroup, once is enough). The final product is then recovered by filtration."

Yield is about 4% of dry seed weight.

While this procedure is legal in the U.S. (where harmine and harmaline are currently unscheduled), it is illegal in Canada where harmine and harmaline are Schedule III. These are extremely potent alkaloids. Misuse of them can result in serious, even fatal, consequences. Read the info about MAO inhibitors.

Comments on this method by Dirk:

White vinegar contains 5 to 10% (5% is 50g/l), look at the label, dilute as appropriate. Say you want 500 ml of 30g/l (=3%) starting with 8% vinegar you'd add 500x3/8 = 187.5 ml of 8% vinegar to 500-187.5 = 312.5 ml of water.

Supernatant is the liquid standing aove the precipitate. Pour as much as possibly off very carefully.

Well i tried it with suction on a buchner filter with a scintillated glass disk. Sound good no ? Well the filter clogged up immediately. There's still some red gum in there. Don't exactly remember how i got around this; possibly used a coffee filter (that ripped). Next time i think i would look for a finely woven cloth.

After dissolving it in hot water you can filter it again, collect the water and add the right amount of table salt. The amount of water to use should be minimal (minimizing loss because of the harmaline/harmine that doesn't precipitates), but not too little (loss through the amount of liquid that gets retained by the filter paper).

The paper {Hasenfratz et al., Ann. chim (10) 7,15l (1927)} then goes on to describe the separation of harmine from harmaline, but this procedure is slightly more complicated and not necessary for most purposes. The separation requires the use of a microscope and is based on the fact that when a warm aqueous solution of the hydrochlorides is alkalinized with ammonia, harmaline is liberated only after the decomposition of harmine hydrochloride is complete {harmine forms long needles; harmaline forms plates}). After separation the 2 salts are then further purified by recrystalisation of their salts.

I've found that harmaline and harmine are quite stable in acid solutions even at boiling water temperatures, however when the pH is raised to 11 or more boiling will rapidly remove the fluoresce of the solution (an indication that harmaline and harmine are being destroyed under these conditions).

Ann. chim (10) 7,15l (1927)

The separation of harmaline from harmine is based on the fact that when a warm aqueous solution of the hydrochlorides is alkalified with ammonia, harmaline is liberated only after the decomposition of harmine hydrochloride is complete. The appearance of harmaline is readily detected under the microscope since it consists of plates while harmine forms long needles. The addition of ammonia, therefore, is stopped as soon as crystals of harmaline are detected, the harmine is filtered off and the harmaline recovered from the filtrate by the addition of ammonia, The bases are then further purified by recrystallization of their hydrochlorides.

(discussion about this extraction procedure)
> ...My question is this: will this extraction actually work? I didn't think
> acheiving the HCl would be that easy! I've recently been thinking about how to
> convert pure, crystalline, already-extracted freebase of a syrian rue extract
> into the HCl form, but that would be a lot of work (adding the right amount of
> moles to the right amount of harmala freebase--too technical), whereas the
> above method claims to extract the HCl directly from the acetic acid solution.
> I don't know too much chemistry, so pardon my ignorance here. All responses
> would be most appreciated!

I think the driving force for this reaction (the converting to the HCl salt) is the fact that the HCl salt is insoluble. Thus it seems to "disappear" from the right side of the harmaline-acetic salt <--> harmaline-HCl salt equation. So even if the dfisplacement of the acetate by the Cl is not favorable, giving an equilibrium concentration favoring the acetate, as the HCl salt crashes out of solution, the equilibrium will try and be maintained, forcing more of the HCl salt to be formed.

I do think this would work, but Id be careful not to add too much NaCl, or else you will get it crashing out as well when you cool. This will skew your yield and cause you to think you have more harmaline than you have. Cooling slowly may help this problem as well (keeping the solution supersaturated with NaCl instead of precipitating out).


Bilbo's Comments On Syrian Rue Extraction: (1996)

Do try to *defat* the potion while it is still in the acidic aqueous phase. You can then get rid of the oily residues then, then change the aqueous to a basic solution @ pH9 - 10, and multiply extract THAT into your non polar solvent; evaporate, and try. Be very conservative with measuring your dose. Anything over 100 mg. of extract should be aproached with caution.