Date: Sat, 13 Dec 1997 15:57:19 EST
From: (Dirk Teunis)
To: Multiple recipients of list <>
Subject: Harmaline Extraction from Syrian Rue

In a message of 11 Dec 97 Hara Ra wrote to Multiple recipients of list:

 HR> Per some interest on this list, I am posting my harmaline extraction
 HR> method from Syrian Rue seeds. I could not find my notes on this, so
 HR> this is from memory and the details may be different. Please bear in
 HR> mind this is for informational purposes only.

I don't want to rain on your parade (this being my first post to this list)=
, but there's a much more practical extraction procedure that would leave=
 you with a significantly purer end product.


 HR> 3. Do NOT EVER attempt injection of the extract prepared by this
 HR> method. It is very possible that this extraction may have components
 HR> which are orally harmless but dangerous if injected.

This warning is important enough to be repeated, further more i don't recom=
mend even eating this extract without first reading up on it. I don't takes=
 responsibility for your actions (you're an adult with all that this encomp=

 HR> Go to the hardware store and buy a gallon of methanol or denatured
 HR> alcohol, and a gallon of mineral spirits (paint thinner). <snip snip>
 HR> I tried this substance, assuming it was 1/3 harmaline and had nausea.
 HR> This was due to the fact the extract was more like 2/3 harmaline. =

 HR> NOTE: This is freebase harmaline. The hydrochloric acid in your stomac=
 HR> will convert it into harmaline hydrochloride...

It will be a complex mixture that also contains any water soluble compound=
 in the seeds.

My hairs always stand on end whenever i read a method that uses mineral spi=
rits and ends with a product that is meant for human consumption. Mineral=
 spirits have a wide boiling range (upto 200C for white spirit) and it coul=
d prove difficult to remove the last traces of it in the final product.

Below is a simple extraction procedure that use only products that are sold=
 for human consumption (with the exception of the Peganum harmala seeds) an=
d no, potentially problematic, organic solvents. The extraction uses the pr=
operty of harmaline and harmine hydrochloric salt that are not soluble in=
 a cold table salt solution.

The advantage of this procedure is that it only isolates the harmaline and=
 harmine and leaves out most other compounds and betacarbolines present in=
 Peganum harmala seeds (harman, harmalol, ...).

All that is needed to perform this extraction is table salt (sodium chlorid=
e), vinegar (acetic acid) and water. Harmaline has a bright yellow color an=
d shows up bright yellow/blue under UV light (black light) even with a smal=
l amount in a largish volume of water.

>From "The Alkaloids" Vol. II by Manske (p393). Printed without permission.


The crushed seeds of Peganum Harmala are covered with three times their wei=
ght of water containing 30 g of acetic acid per liter of water [white vineg=
ar usually is about 50g / l or 5 %; but read the label in some parts of the=
 world 8% is the most common concentration for vinegar]. The seeds swell as=
 they absorb the liquid and form a thick dough which is pressed after 2-3=
 days [use a piece of cloth to do this]. The pressed seeds are once more tr=
eated as above with twice their weight of dilute acetic acid and, after mac=
eration, the liquid is again pressed out. To the combined liquors, sodium=
 chloride [table salt] (100g. / liter of liquid) is added to transform the=
 acetates of harmine and harmaline into the hydrochlorides which are insolu=
ble in cold sodium chloride solutions and are precipitated during cooling=
 [leave the solution in the fridge overnight]. The supernatant liquid is si=
phoned off, the crystalline residue filtered with suction [at this point a=
 {expensive} buchner scintillated glass filter clogged up with some sort of=
 gum, a less sensitive filter might be preferable here] 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 [ones or=
 twice usually is enough]. The final product is then recovered by filtratio=

150g seeds yielded about 6g of fluffy yellow powder.

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 separat=
ion 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 hydrochlori=
de is complete {harmine forms long needles; harmaline forms plates}). After=
 separation the 2 salts are then further purified by recrystalisation of th=
eir salts.

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

Dirk [*]