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Harmalas extraction-syrian rue (by SAKKADELIC)

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Sakkadelic

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After reading some harmalas extraction teks on this site and understanding the basic ideas in them i tried to follow a similar method but with some modifications that i made and after repeating few times it turned out to be good. i hope for this method to be helpful for all and a good contribution to the site.

-why using this method?
This method is very easy to follow, it skips all the annoying filtering and produces high yields of clean harmalas.


-short description of the method:
soak whole syrian rue seeds with water and vinegar
freeze/thaw
boil vigorously in microwave
strain through a metallic strainer(or 100% cotton cloths) and press the liquid out of the seeds
mash with potato masher
repeat boiling/strain/press/mash 5-6x
combine strained liquid and basify with lye
settle and decant water
add water and vinegar, settle, filter, keep liquid
basify
water washes
add minimal amount of water and vinegar
manske
filter crystals, press water out with tissues, dry
collect HCl harmalas crystals
convert to freebase if FB is desired
dissolve crystals in hot water, basify
water washes
settle, decant, dry
collect FB harmalas


-resources needed:
whole syrian rue seeds(up to 100g more than that things get messy, larger volumes, hard to handle and strain...but can be done)
1L glass casserole or big wide jar(for microwave boils)
1L+ jar, 500ml jar, spare jars of different sizes that might come in handy
pure NaOH powder
distilled white vinegar
tap or distilled water
rock salt
microwave
freezer
potato masher
metallic strainer or 100% cotton clothes
large coffee filters
10ml syringe

step 1:acid boils (in this step the jars are very hot, use a towel when handling them)

-in a 500ml jar soak the whole seeds with 20ml vinegar and 230 ml warm water, stir and let them sit for 30 minutes, you could boil them a little if you want the idea is to soak them well and make sure they absorbed water. close the lid and put in freezer, once they are hard frozen remove the lid, put in microwave on thaw(on low). pour into the boiling glass container(casserole or wide jar) and put in microwave.
{
-boil 5 mins on high, let the casserole rest for 5 minutes stir then boil again for two minutes(if you are using a jar keep checking it might boil intensely and spill in the microwave if this is about to happen stop the microwave for few minutes then continue, placing a wooden spoon across the top of the jar will solve this problem and u can boil for longer but stay alert).
-let it rest and cool a bit then strain through the metallic strainer or the cotton cloth into the collecting jar or some temporary container(easier if you couldn't firmly fix the strainer/cloth to the mouth of the collecting jar then transfer later to the collecting jar), press/squeeze the seeds strongly until they are drained. if later the collecting jar was completely filled use one of the spare jars.
-put the seeds back into the casserole mash them slowly with the potato masher (be careful not to break the casserole sometimes there is small stones with the seeds) add 20ml vinegar and 230ml water.
}repeat this 5-6 times.


note: no need to follow procedure and volumes precisely, boil in enough water and vinegar strain and SQUEEZE the water out, achieve this the way that suits you.

-end of step 1:
you should end up with a dark brown/red tea in the collecting jar.
wait until it cools and start step 2, you can put it in the fridge but don't let it get really cold

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step 2:basifying
-prepare a strong solution of NaOH by dissolving around 50g of lye in 250ml water in one of the spare jars, first take all safety measurements before working with NaOH, slowly add NaOH powder to the water stir carefully until all powder is dissolved, this reaction is highly exothermic the jar will become very hot and the water might boil so be careful, this solution will be used throughout this extraction and probably in another one so store it properly if possible.
-when the tea is at room temperature, stir then using the syringe add the lye solution slowly and witness the beauty of this reaction, when the solution turns all milky stop adding lye, if there's still a distinct yellow tint in the cloudy solution add few more drops of lye until the tinge disappears.
-wait few hours until all the freebase has settled at the bottom, and pour slowly as much as possible of the liquid in the drainer be careful not to pour any of the precipitate along. i am impatient and don't have a lot of time usually so i just wait 2 hours max, there would be still some very fine FB floating around but it seems inconsiderable so i pour it, optimally wait 8 hours.

-end of step 2:
you should end up with a dark beige mud.

---------------------------------

step 3:removing impurities
-using the cleaned syringe add vinegar to the mud and stir until nothing is dissolving anymore, these are plant material sometimes they look similar to FB harmalas but don't add too much vinegar to dissolve them, they won't dissolve, so when the solution is not cloudy anymore and if you could measure PH and reached PH 4 stop adding vinegar.
-wait for the impurities to settle (1/2 hour is good), fix well a coffee filter on the jar and wet it with water, pour the solution slowly through the filter leaving the impurities to filter at the end so they don't clog the filter from the beginning, discard the impurities.

-end of step 3:
you should end up with a clearer brown to yellow liquid.


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step 4:re basifying and water washes
-stir and then using the cleaned syringe add the lye solution slowly until it turns all cloudy it will be more beautiful this time fill the rest of the jar with water, wait few hours for settling, decant water
-refill the jar with water, wait for settling and pour the water out this was a water wash, i usually do this until when i rub a drop of the water with my fingers it's no longer slippery(don't forget to wash your hands immediately), with each additional water wash the water will become clearer and clearer but the PH must not drop a lot so the freebase don't dissolves back into solution.

-end of step 4:
after decanting the last water wash you should end up with a clear beige to white mud


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step 5:manske and collecting the crystals
-transfer the mud to the 500 ml jar, using the cleaned syringe add slowly a minimal amount of warm 50-50 water-vinegar to the mud until it's completely dissolved.
-measure the volume of the solution you have or simply fill an identical jar with the same amount of water
-boil this water in microwave add rock salt and stir until all is dissolved(35g salt for every 100ml water will saturate the solution)
-add the salt saturated water through a filter to the harmalas acidic solution, screw the lid loosely and place the jar in a pot of freshly boiled water close the pot lid and let them sit undisturbed to cool of slowly for at least 12 hours.
-when the beautiful needles has crashed out, give the jar a little swirl so the crystals brake of the sides of the jar put them in the fridge for half an hour to settle and cool a little bit more, fix a coffee filter firmly(using a rubber) on the mouth of a jar and slowly pour first the water layer then the crystal rich layer through the filer, if while pouring the filter got filled stop for a minute until the water drips through it then continue, place the lid on the jar and leave it to drip the water.
-once the filter stops dripping water take it and fold it and fix it with clothespins or anything similar so the crystals are safe inside
-place the filter between 2 folded tissues on a dish, flip the filter and replace tissues every few minutes do it until no more water is coming out on the tissues, u can exert a little pressure on it with your hand to force more water out on the tissues, this will ensure that most of the salt contaminated water is out and you'll have a purer product
-dry the filter in front of a fan or using a hair drier, make sure that the filter is cracker dry before collecting the crystals (it will take around 15 mins using a hair drier).
-collect the crystals and store.

(sometimes when working with smaller amounts i proceed a little differently i calculate the amount of salt needed to saturate the volume of harmalas solution, boil in microwave and add a little bit less of the calculated amount of salt to it and stir until most is dissolved then filter the solution and continue normally, i get same results but i believe it's better when the harmalas solution is not saturated enough-with harmalas-).


-end of step 5:
you should end up with beautiful golden thin chips/foils(if using hair drier) of harmalas HCl crystals.(that's the best way i can describe them)

------------------------------------


step 6:freebase
-in a 500ml jar dissolve the crystals with a minimal amount of hot water, add lye drop by drop and swirl gently until the solution turn cloudy
-top the jar with water and rub a drop of the water in the jar between your fingers(wash hands immediately) if it's slippery then you need need to do more water washes, once it is not slippery anymore, dip the tip of your finger into the water then taste it, it should be tasteless, if it is sour or burns a bit then do more washes until is tasteless tasteless and feels like normal water.
-after the final wash let the jar sit until all freebase has settled at the bottom, decant very slowly as much as possible of the water, pour the mud into a narrow cup, wash the jar with few mls of water and into the cup. let it settle very well for many hours and with the syringe remove as much as possible of the water layer.
forget about using the syringe to remove the last bit of water, use a folded paper towel to slowly suck up most of the water, don't let the paper towel touch the freebase layer, picture describes it best.
-pour the mud in the cup into a wide dish and wash the cup with few mls of water and into the dish, dry it overnight in front of a fan make sure it's completely dry before scraping with a razor blade it will be very powdery when it's well dried

(right before complete drying if the freebase is scraped it will form a paste, if you dry this paste in oven on low setting you will get a solid peace like chalk that you can break into small stones of FB harmalas instead of the very fine powder, i like to do this bcz it's easier to handle and to smoke as it is through a pipe or bong, if you smoke a good amount of FB harmalas through a bong you will really get blown away, i wanted to write a post about the smoking experience of pure FB harmalas through bong experienced by me and 2 other friends but it's hard to describe this kind of effects, it's quite intense...)

-end of step 6:
you should end up with a clear beige to white freebase harmalas powder.

------------------------------------

this post was edited so sorry if any of the comments seem irrelevant.
images attached below are of different stages of the extraction and sorry for the rotated and not in order images.
 

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Jees said:
As promised, I gave some of the ideas here a try

Jees: In your ground seeds tek maybe you should have tried boiling them instead of cold soak? I wonder what yields you'd get with this whole seeds tek if you cold soaked them?

PLUS: I am a great fan of your video tutorials. Could you do one about this? Or better still do one from start to finish with every step, aka 'rue extraction for dummies'?

Love them blue gloves, and sandals. Maybe put a glove on them toes for sake of purity, (must not offend the rue.) 😁
 
Thank you.

In your ground seeds tek maybe you should have tried boiling them instead of cold soak? I wonder what yields you'd get with this whole seeds tek if you cold soaked them?
I've thought about boiling and/or freeze-thaws on the grind seeds, just never got to it inspired by being contempt with the yield. It might add something.

Cold soaking whole seeds, hmm, doubtful, but we have a standard expression at work when someone comes up with an idea: "Great, now you are going to try this out!" 😁

I understand it would be neat to have a chart with all possible actions and what their effect is on the outcome. We could give a prize tag on the most important one and a boo-tag for the action that does little. Such chart would be a nice-to-have but takes a lot of comparing works to get to it finally, and then Steven Stokes comes along to tell that his boils are more effective than my boils and we're back at zero. :lol: Or Brenda Bullcock chimes in and tells us to grind even more finer for better etc etc. And perhaps they are right.

BTW one must wear blue gloves, no yellow ones or the yield suffers, and not any sandal works, must be Birkenstock! No sh*t.

* * *

Sakkadelic, yes would be nice to eliminate the overkills. I think center of gravity is the hitting the whole very mushy seeds mechanically strong so their inner content comes out, with whatever means and repeat that. Something like this would be nice:
41dYgYnYn5L.jpg


When watching how apples were pressed juiced, it was important to put them in a cotton bag. I would also do so with the seeds.

Or putting an amount of the seeds in a muslin bag and squeeze it with something like this:
201035.jpg


I'm still wondering on the impact of the microwaves, does it more than just heating? I did waved mine shortly to try it (and finding out my oven wasn't good enough, no rotating plate --> heat spots) so I switched to standard boils.

The towel squeeze trick works best for 50 gr seeds at a time so your hands have a good firm grip over the ball of seeds. It's hard to overpower a too big ball like 100 grams in it.
 
i don't think the microwave has any impact other than heating it's just faster...
i now know what to buy next :) thank u jees
this is what i use one jar is usually not enough for all the liquid so i use two then combine after the first basification.
there's no way i can get it right, i tried it straight and it got flipped to the left i tried it flipped to the right and it didn't flip back, only the picture with iphone worked
 

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Hi guys,

Just finished a SR extraction with whole seeds. Just wanted to give my feed back.
I ended up with 2.7g of clean extract from 50g of seeds. (5.4% yeild)

My process.

4 x 30min boil of seeds at pH 4.
Collected tea, discarded seeds.

Based tea to pH 12.
Allow to precip in fridge 8hrs.
Carefully decanted 90% of base water, poured remainder with extract via filters.
* This filtering was difficult. Did in 4 batches, replacing filter each time.
Washed extract off filters in acid water - pH 4
Poured acid water with dissolved extract via filter again. Discard filter.
* This filter was a lot easier - one batch slowly.

I then perform these steps again, base/filter/acid/filter.

Then one final base - allowed to precip in fridge overnight.
Then I washed the base 4 times with water to lower pH to 8.
(Decant 90% base water, add fresh water, settle (30min), repeat.

Last step - decanted 90% of water - then pour the rest with extract via filter.
Scraped the wet extract from filter onto ceramic dish.
Allow extract to dry over night then scrape with razor and chop up to fine powder.

I started the process Friday night and Monday morning i was scraping up my ready to consume harmala/harmine extract.

Final product was a light beige powder with a consistency similar to talc, taste test was not bitter - no flavor at all really.
 
Sakkadelic said:
i don't think the microwave has any impact other than heating it's just faster...

Au contraire mon frere. Microwaving does more than just heat!

Recent Extraction Techniques for Natural Products Paper

from the document: "In the case of extraction, the advantage of microwave heating is the disruption of weak hydrogen bonds promoted by the dipole rotation of the molecules."

and

"Localised heating leads to the expansion and rupture of cell walls and is followed by the liberation of essential oils into the solvent"

I know we're looking for salts here rather than oils, but rupturing the cell walls is certainly what we want to do!

It helps to have a newer microwave that provides a more homogeneous field and a variable inverter to deliver ~600w of power (most microwaves pulse their highest power only).

Since Jayrocco was able to get good results with whole seeds, I'll try an extraction with whole microwaved seeds (after one freeze/thaw). I'll be back with results in about a week!

Thanks Jayrocco for posting results of your experiment!
 
You're welcome. I figure if we can spare the mess and the filtering difficulties of having powdered seeds - it would make this process much easier.

The upper yield with Syrian Rue extraction is around 6% with crushed/powdered seeds.
My yield of 5.4% is 80% of a 6% yield. (I believe i may have lost some yield during the first filter fiasco)

So either the acid boils penetrate far enough to get 80%+ of the alkaloids from whole seeds.
OR
80%+ of the alkaloids are in the coating/shell of the seed.

Lets stop with the mess and just use whole seeds!
 
Thank u Nightgazer for correcting me, i hope u get good results too :)

Jayroco maybe u got less yields because u didn't do enough boils or did u squeeze the seeds?
And did u use normal coffee filters? I find it hard to filter the freebase with coffee filters without loosing product, i think it's better if u just filer the acidic solution..
I find my extract to be a bit bitter maybe there is some impurities left because i don't do filtering i will try to filter as proposed by BongWizard and report back.
 
Wow Sakkadelic, that wooden plunger seems very rigid stuff :shock: , no wonder you got good results. And that metal mesh seems so fine that it acts like a cotton bag (to put the seeds in). Though I would still favor an extra muslin bag (or a fine cotton sheet) during squeezing.
il_570xN.184749217.jpg



Sakkadelic said:
jayrocco said:
... I find it hard to filter the freebase with coffee filters without loosing product,
i think it's better if u just filer the acidic solution...
I agree, there's really no use to filter the very first based liquid. Even more: better to do some A/B transitions before the first filtering of acid liquid takes place, how much A/B's depends on the clear-ness of the liquid showing. Once you have filtered in acid stage, the next filtering of base will be a piece of cake no doubt.

Jayrocco, 5.4% is neat for whole seeds :thumb_up:
We must also not forget that % yield is not solely a factor of extraction technique, the potency of used seeds is mandatory, and can vary even greatly. Therefore when comparing workflow/yield one should actually use same batch seeds, something I was able of comparing the grind-workflow vs. squeezed-whole-seeds.


Thus so far we have 3 potent (combined) candidates for success, Sakkadelic tek ;)
- freeze/thaw, say 2 times;
- microwaves in the process (thx Nitegazer);
- squeezing them seeds hard before re-boiling.
 
I totally agree with everything u said jees there so many new ideas i want to try, i'm waiting for the new batch to arrive i hope it's good quality
Is there anyway we can move this to the harmalas section??
 
About the microwaves:

Nitegazer hints (thank you!) to the document in attachment.
Can people with lab background interpret this document in relation to our usage here?
Or add info in general about microwaving for our purposes?

What comes to my mind is if the rue seeds have to be totally submerged (boiled) or only moistened (like soaked + strained) for the microwaves to have their cell disrupting effect?

We have this thread: Microwave Assisted Drytek (MAD Tek) microwaving bark in soup consistency, not dry not watery.

And this thread:[Technique] Microwave-Assisted Extraction.
In post #19 someone did rue with minimal water!
BundleflowerPower said:
I did a simple experiment with P. Harmala. 12 g was covered with a minimal amount of water which was acidified with 1000 mg of vitamin c. This was microwaved for 1 min.

A freind and I then consumed the rue along with 10 g each of normaly prepared ACRB brew. We drank this over the course of an hour and a half. A very powerful experience resulted.

The tea made from the rue was also very easy to drink compared to the normal 3x boiling method.

I should note that the effects of the rue seemed a little different than normal. More of an electric feel. Perhaps some of the harmalas were reduced to THH in the microwave?

Edit: today I decided to attempt to brew acacia using this method, a sort of bio essay guided research. I covered 5 g of ACRB in a small glass and covered with minimal water. No acidification used. Microwaved for 1 min. I had 140 mg of harmalas which I re-constituted in water and drank, followed 15 min later by the light.

It works. It was almost as powerful as the 6 g rue + 10 g ACRB brew I mentioned above.

Btw, the taste was very tolerable. Better than the egg white trick or letting it decant over and over.
I find 6gr rue overkill, but if he did only what he said then a shallow extraction might have occurred. This might be reflected by the "very easy to drink" remark.
 

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Good idea putting out the call, Jees, being that I am *not* a trained chemist. 😁

I do have some basis for how I will proceed, however--- see the attached document that provides some assistance with use of microwave for different solvent/solute combos.

Here are some useful sentences providing guidance:

"increasing the power will generally improve the extraction yield and result in shorter extraction time. On the other hand, high microwave power can cause poor extraction yield because of the degradation of thermally sensitive compounds. Also, rapid rupture of the cell wall takes place at a higher temperature when using higher power, and as a result impurities can also be leached out into the solvent together with the desired solute"

I am not worried about the harmalas being fragile, since the microwave should only heat the solvent to 100c. I don't want to pick up too many impurities, however. The good news here is that a properly tuned microwave may be able to release the harmalas with less impurities, though we won't know til we try.

" In many cases the extraction recovery is improved by the matrix moisture, which acts as a solvent. The moisture in the matrix is heated, evaporated, and generates
292 Fundamentals of Microwave Extraction
internal pressure in the cell, which ruptures the cell to release the solutes, hence improving the extraction yield."


Hence the soaking

"occasionally, when longer extraction time is required, the samples are extracted in multiple steps using consecutive extraction cycles, which are also an example of the use of a larger amount of solvent and higher microwave application time. In this case, the fresh solvent is fed to the residue and the process is repeated to guarantee the exhaustion of the matrix. With this procedure, the extraction yield is enhanced, avoiding long heating."

YAY! BTW, over heating with time seems to present the same problems as too much power, so the issue will be how many impurities will we get with the desired amount of salts.

" in conventional extractions, the use of large volumes of solvent increases the extraction recovery. Studies reported that the extraction solution must not exceed 30–34% (w/v). In many applications a ratio 10:1 (ml/mg) to 20:1 (ml/mg) was found to be optimal"


By using four cycles of 3:1 water:seeds (33% w/v), I have a total 12:1 ratio.


Soooo-- I am open to suggestions, but expect to run each solvent run on high (1200W) for 5 minutes each. See the example given for pectin from grapefruit.
 

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Bookmark for myself (and for feedback):

One of the problems extracting the harmala acetates from rue is that the vinegar/water solvent is very non-selective, and drags along many undesirables. Harmala acetate is not very soluble in many common solvents (methanol, ethanol, etc). An the alkaloid form is generally not soluble.

So might it make sense to first extract the undesirables from the seeds with a solvent that won't select harmala salts? The amount harmalas lost in the process might be made up for by not having to filter and wash as much. Microwave use may make this initial extraction quick and efficient.

The question is, what is the most non-selective solvent in which harmala salts are insoluble? Ethenol?Or maybe use Basified water for the alkaloid (perhaps at ph10)?
 
I don't have quantitative data, but when I tried 95% ethanol on rue extracted harmala HCl, it appeared that quite a bit did dissolve. Naphtha on the other hand seems to not pick up any amount of harmala HCl.

Once I ground up some rue seeds and did a butane extraction on it, like I used to do with cannabis to make hash oil. I got a golden yellow oil. The seed residue was used in a standard Tao of rue extraction, but it still did not filter easily and several cleanup stages were still required before good looking product was obtained. So it seems like a nice way to get to the seed oils, but not a particularly effective cleanup.
 
Excuse me if i sound rude, but is it possible to keep this tek as simple as possible?

Jees seems to have gotten excellent results with just water and cheap household products; Do we need to make this extra complex/costly for minimal gain, i ask?
 
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