I am still a total beginner in the world of fermenting - may that be foods, herbs or drinks - but since I love the Syrian rue I thought I would give it a try.

It is possible that biogenic amines such as tyramine are forming in the process. The combination of MAO-inhibitors and tyramine can lead to unwanted and potentially dangerous effects such as hypertensive crisis, migranes and vasoconstriction.

The initial idea for making this tea comes from the ayurvedic understanding of how different tastes work on different body types. This applies not only to different foods but to herbs as well. So the idea is to change the predominantly bitter taste of the harmala tea to more sweet and sour which is more suitable to my body type - especially if one takes it more regularly.

I've made a tea (water extract) by boiling 20 g of ground Syrian rue seeds more than 3 times. I used no acid to make the tea and I did a crude filtering with cotton balls. The end volume of the tea was 1 liter. Then I added 52 g of molasses to the tea and a splash of EM-1. EM-1 is a mix of different strains of Lactobacillus bacteria, photosynthetic bacteria and yeast. EM stands for 'effective organisms'. I put the mixture in a 1 liter jar and sealed it to make anaerobic environment in which these organisms thrive.

After 3 days of fermentation on room temperature in a dark place I was surprised to see a lot of going on. Many bubbles of C02 forming - tea is now fizzy drink - and the taste indeed did change to predominantly sweet and sour with a tinge of bitterness in the background.

For now I only tested a dose of liquid worth for 1g of seeds. I did experience the very familiar effects for that dose. I intend to explore higher doses as well. Also I've made another batch of tea with same quantity of seeds and water without the fermentation organisms so I can have a control.

There are other interesting questions and ideas here that arose only after the initial idea. I did some quick research into Lactobacillus. It turns out that some species/strains can make biogenic amines such as tyramine and phenethylamine, but for that occuring one would most likely have to add proteins containing phenylalanine and/or tryptophan and/or tyrosine to the mix. I read several reports of people achieving euphoric effects with combining MAOi and phenethylamine. There are many other biogenic amines for which I have no idea what kind of effects could they create by themselves or by combining them with MAOi.

Also I am wondering if it is possible that any of these organism are capable of changing the structure of the beta-carboline compounds found in P. harmala seeds (harmine, harmaline, traces harmalol and traces of tetrahydroharmine).

I still have to make more research into the various species/strains of Lactobacillus, photosynthetic bacteria, yeast and other organisms that can be used for fermenting. Also I intend to make more research into different biogenic amines and trace amines. Most likely I will make more posts in the thread after I gather more information.

I find all this very interesting and therefore decided to already make a post about it. Of course there is the idea that other members could join the discussion with their knowledge, experience, ideas and thus enhance the efforts.

Links:
https://www.the-compost-gardener.com/em-1.html
https://en.wikipedia.org/wiki/Biogenic_amine
https://en.wikipedia.org/wiki/Trace_amine

Interesting, i wanna try this.

Cool project, glad someone tried this. I had the same idea when I first had gotten on the rue train and was experimenting with a bunch of different stuff. Never got around to fermenting but one thing I did notice was extractions seemed to give off an odor that goes away over time if you keep shaking/stirring. I wondered if this was some sort of gas they generated, the seeds certainly have some very pungent odor giving compounds in them. The wikipedia article says the astringent vapors of the leaves of the plant are even used to bleach wheat. https://en.wikipedia.org/wiki/Peganum_harmala#Uses I wondered if those vapors might be psychoactive or related somehow, I actually tried inhaling the pungent air from a seed soak I was doing by leaving a bag over it but didn't notice much. Wouldn't be that surprised if it had some effect, aromatherapy has proven benefits even if it's 'all in your head.' But the vapors the leaves give off I think gave me the idea to ferment the seeds.... Since fermenting a lot of times gives off gasses, dunno thought it might do something interesting to the effects or maybe convert some of the alkaloids.

Should be able to tell pretty easily if there's any chemical change via a TLC, or even just the effects/taste. Drink 5gs of high harmaline rue and it's gonna be unmistakable that you just drank 5gs of high harmaline rue . The fact that you say it's sweet could indicate a harmaline chemical change, but it also could just mean it's being masked. I've found citrus masks the harmaline taste very well. Drinking 5gs+ and seeing if you get characteristic harmaline tracers and drunkenness should be a pretty reliable test though. I'd be most curious about potential conversion of harmine/harmaline, since we know those chemicals undergo change in caapi brews. I have also observed what seems to be 1 other compound in rue ( harmalol? just posted about it here https://www.dmt-nexus.me...aspx?g=posts&t=94489 ) . That compound seems pretty volatile so maybe something could happen there too.

You could also maybe do a manske to separate any potential tyramine though I'm not well versed enough to know if that could come out in a manske as well I'm just assuming it wouldn't.

Interested to hear any further bioassays you do Trig!

Hey! Mooai thanks for joining in the dicussion!


I have never thought before of a possible volatile compounds that are psychoactive in P. harmala seeds that are not essential oils which I had observed floating at the top of the tea. The smell that forms when cooking the seed tea is indeed very interesting - I quite like it actually. For now I am quite sure that the gas forming at fermentation is the typical CO2, I could be wrong of course.


I have not bioassayed a bigger dose yet so I cannot say if there was any conversion. For now I think that the reduction in bitter taste is because it is masked by the sweet taste of molasses and the sour taste of lactic acid made by the lactonacillus in the EM-1.


I've got not idea about tyramine falling out with manske. However if there is any potential conversion of the alkaloids happening I would definitely try to clean the tea with manske and bioassay those alkaloids and compare that to the water extract.

I did observe a very strong fermentation process going in the P. harmala tea I've made and put to ferment. The reaction seems stronger compared to when I make a regular molasses solution to ferment with EM-1 just to make more EM-1 - and that I find very interesting. I thought that the compounds in P. harmala would reduce or totally stop the fermentation but that is far from the truth I see now. Also the two quotes bellow give more interesting information about this. It seems the mystery deepens.

These two quotes are from wikipedia: https://en.wikipedia.org/wiki/Peganum_harmala


Any ideas what could be going on here ?

And this is what I think mooai mentioned above:

I did a series of bioassays with the fermented harmala seed tea. They mostly consisted of me taking a relatively small dose before sleep, that is from 1g to 1,5g worth of fermented liquid. Also I did one bioassay with 3g dose, however I was somewhat tired from the cannabis I smoked a few hours before that. Therefore the effect was a little diminished.

The 1g - 1,5g doses before sleep were very pleasant, smooth, providing relaxation in the body. I had easy time falling asleep after putting down a book. I observed an effect on dreaming as well. The dreams were more vivid than usual, with a very consistent 'story line' and engaging. In the morning after waking up I was left with a very nice afterglow and smooth feeling in the body which lasted at least an hour after waking.

I dosed the 3g dose on a trail with 3 steps by each time taking 1g every 20 min. The tiredness from cannabis was resolved and a more energetic state developed. There was typical harmala smoothness and vivid imagination. I did expect the effects to me more pronounced with this dose though.

I think I should have added a little acid to the tea to pull more alkaloids. This will be resolved by taking a larger dose of the fermented tea I have left for future experiments.

What is also important is that so far I did not observe any unpleasant or toxic effects on the body. I am mentioning this because at this point I don't know if there are any 'unwanted' compounds such as tyramine in the fermented tea, since some of the Lactobacilus strains and yeasts can make various 'biogenic' amines.

Regarding the possible conversion of beta-carbolines in the fermented tea. One possible thing that could happen is exactly what this post suggests regarding harmaline conversion to THH, only that instead of using ascorbic acid it is done by lactic acid created by the lactobacilus bacteria. Can downwardsfromzero or any other chemist or member speculate on that ?

Mooai proposed that maybe manske could be done on the fermented liquid. The ph strips indicate that the ph of fermented liquid is ph ~ 3 and the ph of the control tea (non-fermented) I made is ph ~ 7. Sounds quite appropriate for a manske. I will most likely try that in the near future and see what happens.

Redox processes are an essential component of fermentation. Lactic acid can in principle be oxidized (meaning it is acting as a reducing agent) to the metabolic keystone pyruvic acid - which, incidentally, decomposes fairly readily (e.g. https://www.physicsforum...id-decomposition.839140/) to acetaldehyde and carbon dioxide if left alone in solution.

Besides all that, we're looking at a fairly complex, biologically active mixture so even the process of attempting to produce analytical isolates is likely to change what we're looking at. The Manske is likely to precipitate at least some of the compounds of interest, and the presence of sodium lactate in the remaining solution is unlikely to confound crystallization because it is very soluble.

It will be interesting to see how the effects Manske'd alkaloids compare with those of the whole fermented brew.


On a slightly related note, I made an observation while taking far too long to process some rue tea earlier this year.

My main focus was getting the brew to a crystal-clear state before proceeding further. This aim was fraught with the usual fine suspended solids and compounded by a persistent pectin haze. Addition of a small amount of alum (potassium aluminium sulfate)ª solution had had some beneficial effect but it was still not wholly satisfactory.

The weather warmed up and my brews all became inoculated with a Trichoderma mould. As chance would have it, Trichoderma can be an abundant producer of cellulase: this observation became apparent as several of my filter papers literally dissolved away while in contact with the - now technically fermented - brew.

The happy upshot of this was that the cellulase also seemed to be active against the pectin (which, rather, may have been a soluble hemicellulose?) - the solutions began to clear. Before the mould got out of control and started to produce spores, it was brought to an abrupt halt by the addition of concentrated acetic acid to make a 1% solution. Again fortune shone upon the haphazard experiment and the mould congealed nicely, taking some more of the sediment with it. This also seemed to be sufficient to inactivate any remaining cellulase.

After standing for several more weeks (while life got in the way), the once-again-filtered brew deposited the remainder of its extremely fine sediment leaving a now truly crystal clear solution. When a light beam was shone through it, it was no longer visible from the side (no Tyndall effect).

I'm reluctant to use Trichoderma-treated brew, however, as I'm uncertain of its toxicology. Since it's already acidic I'm contemplating Manske as the next step, but it is very dilute (50g seed in ~5L brew.) On account of this acidity, it seems daft to add alkali as some suggest. (Sorry for the slight thread-hijack!)

ª Alum is often included in tradition esphand incense from the middle eastern grocer's store and is well known for being an astringent, mordant and coagulant.

downwardsfromzero thank you for the kind reply.

I will keep you updated.

Continuing (concluding?) the tangent: Trichoderma mould produces (amongst other things) gliotoxin - a tremorgenic, immunosuppressive, anti-inflammatory substance. Freebase + Manske should get rid of it.