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root extract of syrian rue / peganum harmala / harmine / harmol Options
 
Triglav
#1 Posted : 6/21/2020 10:12:13 AM

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Yesterday I was reading this thread on the forums --> https://www.dmt-nexus.me...p;m=1063718#post1063718 where another member Jees posted a study which I will post again here in this thread.

I read the study and found there's a very interesting piece of information available in there.

quote from the study
Quote:
The molecular profile of alkaloids highly varied in the plant with harmine and harmol predominating in roots and harmine and harmaline in seeds. Interestingly, harmaline occurred almost exclusively in seeds whereas harmol was mostly present in roots with traces found in stems.

I had played with the idea of trying harmol or harmalol some times in the past, but now with concrete information that there is approximately 1:1 ratio of harmine:harmol in the roots of the plant this idea becomes more tangible.

This plant also grows wildly in some parts of the USA and the mediterranean. Maybe someone could collect the roots of this plant and play with the extraction of those. The folks behind the study collected the plants in Spain.

I suspect it should be possible to separate harmine from harmol in a similar fashion as with harmine and harmaline. It would be interesting to separately explore the effects of harmol and also in natural combination of harmine/harmol found in roots. Maybe it's possible to make a relatively simple conversion of harmol to harmalol similar like with harmaline to tetrahydroharmine and therefore explore harmalol as well.

These are some ideas and questions. If you have anything to add please do so. Smile

 

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downwardsfromzero
#2 Posted : 6/21/2020 11:08:16 PM

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Wasn't there an "in search of harmol" thread some months back? Or at least there was a harmol-related diversion within something like the VDS protocol thread... something along those lines to look into. I recall there being some disappointing sludge involved, but that was using seed tea with the main rue alks removed.

Harmol is a bit trickier to handle than harmine because its phenolic group forms an anion under alkaline conditions so it won't precipitate simply by raising the pH. The phenolic group is also more susceptible to oxidation than the methoxy group - a bit of reading of the literature will be necessary in order to get a handle on the best way of separating harmol in a recoverable form.
Ora, lege, lege, lege, relege et labora

“There is a way of manipulating matter and energy so as to produce what modern scientists call 'a field of force'. The field acts on the observer and puts him in a privileged position vis-à-vis the universe. From this position he has access to the realities which are ordinarily hidden from us by time and space, matter and energy. This is what we call the Great Work."
― Jacques Bergier, quoting Fulcanelli
 
mooai
#3 Posted : 6/22/2020 9:43:02 PM

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I'm not sure if it is harmol but I suspect one alkaloid degrading after boiling that I have observed on a couple TLCs above harmaline. Attached is a pic from my experiment thread and I wasn't 100% sure if it may have just been an inaccuracy but I have observed this spot at least twice, only in cold water extracts and never after boiling. Pic attached ( 'mystery spot' ). Something to consider. I'm not sure if it's harmol from the wikipedia article which doesn't mention it in the seeds, maybe more likely harmalol, is this alkaloid heat sensitive?

I feel consuming the seeds straight to be darker/more dreamlike, more visual (with closed eyes mostly) whereas my extract goo from a boiled down brew feels more purely dissociating + tracers, a little less personality maybe so I wonder if that is due to this mystery alkaloid. Even less personality is a manske after boiling, I liked that at first but have come to enjoy the full spectrum more authentic rue experience, maybe a learned taste as it definitely has its tough parts. After toasting the seeds I've observed all the harmalas seem to degrade or vaporize away after seeing no yield from manske, though they still felt like they had a head rushy/lightening effect when eaten, could be the vasicines.

I can't stand eating the seeds straight any more I don't think... Very rough on me, I got a cold water extract going in the fridge right now for next time maybe tonight or tomorrow.

Would definitely purchase other parts of the plant like roots if anyone knows any good sources, I've only ever seen the seeds sold. I want to grow rue too but I haven't had any luck in even getting them to germinate, though I'm quite an inexperienced gardener, don't know what I did wrong. Put them in a wet paper towel in a bag and a jar rinsed/moistened every so often but didn't see any change after a couple weeks. My morning glories are doing great though a ton of sprouts very quickly. I think I have heard rue needs sandy soil, not sure where to get suitable potting mix.
mooai attached the following image(s):
all teas test (slanted...).png (7,584kb) downloaded 80 time(s).
 
Triglav
#4 Posted : 6/30/2020 2:21:53 PM

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downwardsfromzero wrote:
Quote:
Wasn't there an "in search of harmol" thread some months back? Or at least there was a harmol-related diversion within something like the VDS protocol thread... something along those lines to look into. I recall there being some disappointing sludge involved, but that was using seed tea with the main rue alks removed.

According to the study in the first post there is only very very little if any harmol in the seeds of Syrian rue. I find it not surprising that it failed to provide good results in that regard.

Do the experienced chemists have any ideas how to go about retrieving harmol from the solution made with roots ?

mooai wrote:
Quote:
Attached is a pic from my experiment thread and I wasn't 100% sure if it may have just been an inaccuracy but I have observed this spot at least twice, only in cold water extracts and never after boiling. Pic attached ( 'mystery spot' ).

I think it could be harmalol. The study says there are some small quantities in the seeds. Wikipedia says this about harmalol's melting point --> 100 to 105 °C (212 to 221 °F; 373 to 378 K) (trihydrate)[1]. I think it makes sense that this spot only appears at the cold water extract since harmalol seems like it is heat sensitive.


other links of interest:
https://pubchem.ncbi.nlm...h.gov/compound/harmalol
https://pubchem.ncbi.nlm.nih.gov/compound/Harmol
https://www.dmt-nexus.me...&m=498393#post498393
 
Triglav
#5 Posted : 7/1/2020 11:11:08 AM

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After searching and reading the forums I had found the post quoted bellow in the thread from the link: https://www.dmt-nexus.me...sts&t=74123&p=5 | the author of the post is a member called NgatiWikitoria:
Quote:
Peganum harmala root extraction:

Due to severe personal time constraints, I have not written this up for a year and a half. hopefully the GCMS results of the samples posted (and received) last year have been returned.

I haven't had the time to work out how to insert images in-line - and hence I am pasting the text below, and hopefully attaching the PDF version with inline images.

Materials and Method
Materials:

Coffee grinder
Dried Peganum harmala roots.
Sodium carbonate
Sodium hydroxide
Sodium chloride (non-iodised rock salt)
Water
Vinegar
Paper towels
Fine tea pot filter
Smooth tea towel
8mm Stainless steel spatula
150mm glass stirring rod

Method:

All steps were accompanied by Tripping Daisy's albums "Bill", "I am an Elastic Firecracker ", and "Jesus Hit Like the Atom Bomb". This is significant, because whenever I listen to this music (which is fairly often) I recall this, my first exploration into the wonders of isolating certain harmala alkaloids from raw herbal material!

Roots were harvested 2-5 years prior in late winter/early spring (when repotting) from container-grown plants grown in potting mix and pumice. The roots were rinsed of most extraneous matter when fresh, then dried in a domestic hot water cupboard. At the time of extraction, there appeared to be some <1mm diameter spherical fungal fruiting bodies on them following storage in a sealed plastic bag.
Root diameter was from ~5mm down to fine root hairs <1mm in diameter. The relative proportion of root diameters was not recorded. The total weight of dried roots was 26g.

The steps outlined in https://wiki.dmt-nexus.m...ion_and_Separation_Guide were used as a guideline, as follows:
Roots were powdered in a domestic electric coffee grinder until fine airborne powder was present. Some larger root sections were not ground so finely

The root powder was brought to the boil and simmered lightly in water + vinegar as per the above link <<how much?>> in a stainless steel pot for 15-30 minutes. The liquid was filtered through a fine stainless steel tea filter and the filtered liquid retained. The marc was returned to additional water + vinegar. This process was repeated five times, until there was very little yellow coloration in the liquid.

The acidic aqueous extractions were combined and filtered through coffee filters, paper towels and fine cloth tea towels. This final filtration process took several hours due to the very fine particle size.

Following the final acidified aqueous extraction, the liquid was combined
and reduced to 500ml by gentle simmering, then poured into a 500ml jar.

Sodium carbonate powder was added to the to liquid in small amounts using a small stainless steel lab spatula. Some frothing of solution was observed along with some clouding of the solution.
NaOH was then added to further basify. Litmus paper showed that NaOH definitely increased pH by ~2 points - admittedly difficult to tell with the paper and comparison chart in use.

The liquid was filtered through double-layered coffee filters, and the solids retained. (The filtrate was retained for further basification, labelled "Base #1"Pleased

The coffee filters with the filtered solids were placed into 100ml vinegar and hot water added to ~400ml and were vigorous pressed/agitated with a glass stirring rod in order to dissolve all solids.

The liquid was filtered through double-layered coffee filters; although the liquid appeared clear, some dark solids were caught in the filter.

The filter paper and solids were discarded, and the liquid retained for Manske process crystallisation. The total liquid volume was 575ml.

The liquid was heated to simmering, and 69g non-iodised salt was added to the solution, and within 2 minutes was poured into 2 jars to cool to room temperature, and then placed in a refrigerator.

After approximately eight hours of refrigeration, the solution and crystallised solids were filtered through double coffee filters.

The filtered solids were rinsed with the recycled filter liquid in order to concentrate the crystals into the base of the coffee filter. The filters were placed into a hot water cupboard with a toothpick to keep the filter paper open in order to speed the drying of the crystal "mush" in the middle.

Following desiccation the crystals were scraped from the filter paper and weighed. 1.545g of harmala alkaloid salts were recorded.

These solids were dissolved into boiled water. The filter paper was rinsed and the liquid combined.

Sodium bicarbonate was added in order to precipitate (assumedly predominantly) harmine freebase, and left to settle for ~6 hours.


The supernatant liquid was sucked out using a large syringe, then gently decanted. Most of the solids remained settled in the bottom of the flask.
Sodium carbonate was added to the remaining liquid in order to (presumably) precipitate harmaline freebase. There was no apparent clouding of the solution. NaOH was then added to the solution in a further attempt to precipitate harmaline . No localised clouding was observed at all when adding solid NaOH. This reinforces the reports that harmaline is not present in P. harmala roots.

The acidification/basification/Manske process was repeated 4 times. A pale beige freebase powder resulted, with a weight of 1.544g

Based on the above, a yield of ~5.94% of harmala alkaloids of unknown purity and profile appears to have been attained using these materials and method.

The next step is to have this extract analysed, after which conclusions may be drawn and further discussions and recommendations future experiments may be made.

<<Edit 22/3/19: Endlessness has received confirmation from the lab that the extract was analysed as being 51% harmine, no harmaline and the remainder being inactive salts and/or residual water.

This is equivalent to a yield of ~3.02% - call it 3% - harmine from these roots. This confirms previously published reports that the roots contain harmine, but not harmaline, n contrast to the seeds of P. harmala, which contain harmaline and harmine.

Obviously this work needs to replicated in order further elucidate the content of P. harmala roots. It must be pointed out that the intention was to isolate alkaloids that are able to be isolated using Manske NaCl crystalisation.
It is obvious that there were other harmala alkaloids present due to the UV flouresence of the supernatant liquid that was (eventually) discarded after the filtering out of harmine crystals. It would be very interesting to have a raw salt extract from roots analysed to see which other harmala alkaloids are present. This would be especially relevant for those who wish to make a raw tea of the roots for consumption, rather than extracting the harmine: What else is in there? What are the potential benefits be of these other compound? what are the potential risks?

It was confirmed that the roots do not contain any significant amounts of harmaline and do contain good amounts of harmine. However no harmol was detected by the testing done by Endlessness. However the extraction process did involve a step we call manske and the author of extraction says:
Quote:
It is obvious that there were other harmala alkaloids present due to the UV flouresence of the supernatant liquid that was (eventually) discarded after the filtering out of harmine crystals. It would be very interesting to have a raw salt extract from roots analysed to see which other harmala alkaloids are present. This would be especially relevant for those who wish to make a raw tea of the roots for consumption, rather than extracting the harmine: What else is in there? What are the potential benefits be of these other compound? what are the potential risks?

From the study uploaded in the first post we know that the other alkaloid in the roots is mostly harmol. It seems that the manske step removes the harmol or rather leaves behind harmol in the manske solution as NgatiWikitoria suggests in the post.

I see more and more how lack of practical chemistry knowledge is becoming a limitation. Smile I still have to make more research into this. I know there are threads in the forums where members tried to isolate the leftover alkaloids in the manske solution, though with not much success if I recall correctly.

Will update with any new info!
 
dithyramb
#6 Posted : 7/1/2020 9:13:57 PM

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İ have worked with crude root extract of rue. While recognizing the same essential spirit as the seeds in it, it is a whole different thing... Kind of the opposite of the seeds. No talking, no teachings. And strangely did not orally activate acacia. İn my limited experience.
 
 
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