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Harmine, harmaline and THH from Syrian Rue. Verification and finetuning of the VDS-protocols Options
 
BongQuixote
#581 Posted : 1/1/2021 1:57:01 PM
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Happy New Year!

Here are some notes regarding VDS protocol. I've done it 5 times so far, and I could use help peer-reviewing some of my findings.

Boil: I do 5 one hour boils with 7% vinegar. I found that the amount of vinegar suggested by VDS was barely enough to saturate the seeds during the first boil, so got almost no liquid left. I advise doubling the amount of liquid across all the boils. With more diluted liquid trapped in the seeds, less loss of product. I also sparge the grains with hot water after the final boil to rinse out any harmala containing liquid in the seed mass (learned that from brewing beer). I do all my boils in a pressure cooker with the lid closed, but not locked, during boil 1-3 and with the lid locked and 15 psi pressure during boils 4-5. I started doing this with Acacia bark and my yield jumped 30%, so I kept that practice with rue seeds. Having the lid on also prevents the entire house from smelling of vinegar. I also don't grind my seeds. Looking at the VDS results, it doesn't seem to increase the yield enough to be worth the extra mess.

Reducing: I reduce down to one liter for 500g of seeds.

Filtering: First through t-shirt fabric multiple times, then through coffee filters and finally through medium filter paper using a Buchner funnel and vacuum. I save all the filter material and squeeze out any liquid from it. Then I rinse the filters in vinegar and combine that with the squeezed out liquid, let it sit overnight to let sediment settle and then decant off the supernatant and run that through the medium filter paper. Combine that liquid with the filtrate and filter one more time for good measure. This takes me about 2 days, since the first two filtering steps are gravity powered. Just let it sit and drip overnight. I go through maybe 3 t-shirt pieces and 3 coffee filters to get everything through.

Initial basification: I use lye added under magnetic stirring, being careful not to get the liquid too hot. I stop when I get to PH 10 and let cool. I use the same PH meter as VDS, great piece of equipment for the money.

Manske: I follow VDS here regarding method and amounts, insulating the jar while it's crystallizing and sticking it in the fridge after it has reached room temperature (after 8-10 hours). After each re-dissolving I filter the liquid and squeeze out any remaining liquid from the filter. I also save the salty water from the previous round, reduce it down 30%, add some more salt, and give it another round of crystallizing. So I effectively do a double-check to make sure everything mansked out right. Only once did I find any extra crystals during the "verification manske", but it's a easy step and it doesn't delay the process. I manske five times. The previously mentioned red goop usually shows up at the bottom after manske 2 or 3, and it doesn't redissolve so easy to filter out. It tends to have crystals stuck to it, so I don't want to leave it at the bottom of the jar.

Harmine/Harmaline separation: I add 12% ammonia dropwise under magnetic stirring, going slow. It takes me maybe 15 minutes to complete it, with no more that one drop per second of ammonia being added. I found that adding ammonia too fast causes harmaline to precipitate out early, due to locally higher PH in parts of the solution. This become especially important as you get closer to your precipitation point and the PH of your solution is no longer acidic enough to redissolve any accidentally precipitated harmaline. Go slow, it pays off.

Adding ammonia dropwise, keep an eye on your PH meter. Make sure each addition of ammonia causes a rise in PH. You need to give the ammonia time to distribute throughout the solution and for the PH meter so stabilize, so don't go too fast. You will eventually see a PH drop and clouding of the solution. PH might drop pretty far, almost a full point isn't uncommon. Give the solution some time to stabilize and keep adding ammonia dropwise. After each ammonia drop, make sure the PH returns to the same exact value it had before you added the drop. If the PH stabilizes at a higher point, keep adding ammonia until you're around 0.2PH higher than the stable point you identified earlier. This may only take a 1-3 drops. Most harmine should now be out of solution. I've seen this happen as low as PH 5 and as high as 7.

Filter and save your harmine. Add more ammonia dropwise, still being gentle, until you get to PH 9.8 and then filter out your harmaline. This got me a 54/46 ratio between harmine and harmaline, which seems top be consistent with most people's results. I rather stop the harmine precipitation a little earlier than risk getting harmaline in my harmine. Having some harmine in the harmaline is less of an issue for me.

Starting with 500g of seeds, I got 7 grams harmine and 6g harmaline, so a 2.6% yield. Product is very clean with no pigmentation, oils or plant matter left.

After doing this I went back to my old "mixed harmalas" jar and reprocessed everything from the manske steps onward. I lost over 30% of my product, but that was due to the fact that my previous process was sloppy, only 2 manskes etc, so it removed mostly impurities. The I converted half the harmline to THH per my previous post. I find that doing the magnesium reduction to THH works best when you start with clean harmaline.

I did do the sodium carbonate and sodium bicarbonate methods as well, but it was just way too messy for my taste. I think those are great for safety reason, and I will recommend them to any one doing this for the first time since it's hard to hurt yourself by doing it wrong.

Thanks for the note, Elrik. I will try your experiment!



 

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BongQuixote
#582 Posted : 2/2/2021 1:34:00 PM
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Got a microscope finally, and here is how the harmalas look under magnification. Harmine, harmaline and THH in order. There is definitely some garbage mixed in with the THH from the Magnesium reduction, but hopefully just magnesium acetate, which is safe.

BongQuixote attached the following image(s):
Harmine.jpg (598kb) downloaded 142 time(s).
Harmaline.jpg (557kb) downloaded 142 time(s).
THH.jpg (709kb) downloaded 142 time(s).
 
downwardsfromzero
#583 Posted : 2/3/2021 8:45:25 PM

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Some interesting points have come up here. Lately I was thinking about the magnesium residue from that reduction route as well. One way of cleaning up co-precipitated harmala freebase and magnesium hydroxide would be to wash the alkaloids out with ethanol.

I'm currently working on ascertaining if there is a difference in alkaloid profile between material which has been extracted using ascorbic acid and that which has had a less strongly reducing acid. Subjectively, harmala decoction with ascorbic acid seems to be more euphoric. I'll abstain from speculation at this point but the plan is to see whether there is a greater amount of THH present in the ascorbic acid brew.

There are a number of confounding factors in my experiential work that need to be taken into account first and the process of elimination will take several weeks.
Ora, lege, lege, lege, relege et labora

โ€œThere 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."
โ€• Jacques Bergier, quoting Fulcanelli
 
Jules_supertramp
#584 Posted : 2/3/2021 10:32:39 PM

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BongQuixote wrote:
Happy New Year![...]


Nice one, to have a Microscope is pretty handy. Why do you actually separate Harmine, Harmaline and THH? For use as a MAOI it doesn't matter right?

Do you keep the base or the acetate for storage?
...so forth and so on...
 
BongQuixote
#585 Posted : 2/3/2021 11:59:33 PM
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Hi, and thanks! I just got the microscope and it's a blast to play around with. I got the same model as VDS used for his paper, quite affordable.

Separation of mixed harmala alkaloids into harmine, harmaline(DHH) and tetrahydroharmine(THH) is done so you can create the combination of effects you like. I often mix depending on what I have planned for later, "do I need an MAOI?". Since I work with Syrian rue, you end up with about 50% harmine, 50% harmaline and no THH. If you extract from b. caapi. you will get closer to 55% THH, 40% harmine and 5% harmaline. These are all very average numbers and do vary.

For a "syrian rue tea" experience, mix 50% harmine with 50% harmaline
For an "ayahuasca" experience, mix 55% THH, 40% harmine and 5% harmaline
For a "BongQuixote" experience, mix 175mg harmine, 175mg THH and 20mg harmaline

The harmalas themselves have different effects, so it's good to be able to dose to your liking.

Harmine: Uplifting and relaxing MAOI, nice to chill and before bed. I like up to 200mg, after that I get a bit of ringing in the ears and electrical feeling limbs

Harmaline: Like harmine, but 4 times stronger MAOI. When I go 75mg or up, I get real bad nausea, tons of weird chopped up tracers, buzzing in the ears. I usually throw up if there is too much harmaline in the mix.

THH: Only gone up to 200mg, but that was a non event when it comes to side effects. It mitigates the trip, so if you're doing DMT or mushrooms afterwards, it will be a more pleasant trip and I think it helps me make sense of them better. THH is not an MAOI, so for that you need either harmine or harmaline.

So, that's the reason. Makes it a more useful tool with not a lot of extra work. If you're doing extractions and manskes for a week, spending the extra 10 minutes to separate them out in the end is worth it. I had to stop taking harmalas for a while because I always threw up, but once I got the harmaline component way down, no more problems. I think I became super sensitive to harmaline.

I keep the base in jars with desiccants taped to the bottom of the lids. Some of it is years old, but I recently did a re-x of the old stuff with all the manskes and it's still in great shape. I figure I make a big batch every couple of years, and that should be all I need.
 
BongQuixote
#586 Posted : 2/4/2021 12:05:45 AM
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downwardsfromzero wrote:
Some interesting points have come up here. Lately I was thinking about the magnesium residue from that reduction route as well. One way of cleaning up co-precipitated harmala freebase and magnesium hydroxide would be to wash the alkaloids out with ethanol.

I'm currently working on ascertaining if there is a difference in alkaloid profile between material which has been extracted using ascorbic acid and that which has had a less strongly reducing acid. Subjectively, harmala decoction with ascorbic acid seems to be more euphoric. I'll abstain from speculation at this point but the plan is to see whether there is a greater amount of THH present in the ascorbic acid brew.

There are a number of confounding factors in my experiential work that need to be taken into account first and the process of elimination will take several weeks.


Where I live I can't get 100% ethanol, but I assume methanol may work as well? Just gotta dry it!
 
Jules_supertramp
#587 Posted : 2/4/2021 12:49:22 AM

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BongQuixote wrote:
Hi, and thanks! [...]

Cool what microscope is it, like the magnification capacity? My first ever extraction was from VDS's paper (OMG if I think about the filtering Sick ...I have the alkaloid mix for quite a while and haven't even tried it, because of the diet one should do...but 1 day is sufficient I guess of sparing out tyramine? Wanted to just use it subliminally as MAOI for the DMT experience.
I reckon its worth the high when you do it? I remember from reading TIHKAL that Shulgin did't like it much and it involved a lot of puking (even tho he did what I think was half a gram until he was crawling to his bathroom :lolSmile




...so forth and so on...
 
BongQuixote
#588 Posted : 2/4/2021 11:10:01 AM
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Jules_supertramp wrote:
BongQuixote wrote:
Hi, and thanks! [...]

Cool what microscope is it, like the magnification capacity? My first ever extraction was from VDS's paper (OMG if I think about the filtering Sick ...I have the alkaloid mix for quite a while and haven't even tried it, because of the diet one should do...but 1 day is sufficient I guess of sparing out tyramine? Wanted to just use it subliminally as MAOI for the DMT experience.
I reckon its worth the high when you do it? I remember from reading TIHKAL that Shulgin did't like it much and it involved a lot of puking (even tho he did what I think was half a gram until he was crawling to his bathroom :lolSmile


It's a BRESSER Biolux NV 20x-1280x microscope. The magnification is more than enough for biochemistry work. Photos above are taken with the lowest power lens and the camera it comes with.

Filtering rue is frustrating, that's for sure. I just want to throw it all out after 2 days of dripping liquid through t-shirts and coffee filters. Smile

I wouldn't worry too much about diet. I often use harmalas orally within a couple of hours of eating a normal dinner, and I don't stay away from certain foods. From what I've read (sorry, don't have the link in front of me), the MAO inhibition from harmalas does not interfere with your normal digestion, even when eating food with tryptamines.

500mg is a lot. Most anyone did in my house was 400mg mixed harmalas from rue, and that was like being in one of those old A-Ha animated videos with the charcoal animation (https://www.youtube.com/watch?v=djV11Xbc914) , with insane nausea and inability to walk. If you do 200mg harmine and 200mg THH, you will be fine and probably won't have any nausea.

Harmalas extend and expand most psychedelics, and using before smoked DMT gives a better experience. Never tried sublingually, just in gelcaps. Can't stand the taste.

 
Jules_supertramp
#589 Posted : 2/4/2021 11:40:56 AM

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BongQuixote wrote:
It's a BRESSER Biolux NV 20x-1280x microscope. The magnification is more than enough for biochemistry work. Photos above are taken with the lowest power lens and the camera it comes with.

Filtering rue is frustrating, that's for sure. I just want to throw it all out after 2 days of dripping liquid through t-shirts and coffee filters. Smile

I wouldn't worry too much about diet. I often use harmalas orally within a couple of hours of eating a normal dinner, and I don't stay away from certain foods. From what I've read (sorry, don't have the link in front of me), the MAO inhibition from harmalas does not interfere with your normal digestion, even when eating food with tryptamines.

Harmalas extend and expand most psychedelics, and using before smoked DMT gives a better experience. Never tried sublingually, just in gelcaps. Can't stand the taste.


Thanks then I might look into that as well when 1280x is already good for that.
Same feelings with filtering but I think results aren't as good when the plant material isn't grinded, but it's just a mere guess, I haven't tried.

Ah wouldn't be so sure about that buddyWut? ...there are plenty of records from people having had hypertensive crisis due to a wrong diet in combination with MAOI medication. Here is a interesting read: https://erowid.org/chemi...maois/maois_info2.shtml
Maybe that's why some people feel ill and need to vomit?

Ohhh ok...I'll see how it tasts...at least my expectations are down to zero nowCool Laughing Laughing
...so forth and so on...
 
King Tryptamine
#590 Posted : 2/4/2021 12:54:57 PM

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@Jules_supertramp

The source you linked made no mention of the MAOI(s) used and whether or not the type of MAOI being used was the reversible kind as is the case with harmine or moclobemide or the irreversible kind such phenelzine. There's a major difference between the safety of the two types.

Reversible inhibitors of monoamine oxidase A (RIMA) have a substantially lesser presser effect in the presence of compounds like tyramine due to the ability of tyramine to compete with RIMA's like harmine for the occupancy of the MAO-A enzyme, the harmine will be displaced in favor of tyramine on the active site of the enzyme allowing for its breakdown.

The harmala group of alkaloids have no affinity for the MAO-B enzyme also responsible for the breakdown of hypertensive agents like tyramine so its metabolism is also unhindered. The danger only arises when the inhibitors of MAO-A or MAO-B (selective) or both (unselective) are consumed in conjunction with tyramine-rich foods such as aged cheese as tyramine breakdown is partially of fully inhibited allowing for the compound to induce peripheral hypertension.

I believe like with moclobemide, that when consuming harmalas you should pay some attention to your diet like not consuming vasts amounts of presser foods like coffee or cheese but not to be overly concerned with what you eat or drink, unless you're taking it in stupid amounts which most people do not. The main concern when it comes to harmalas is taking it with certain monaminergic drugs like amphetamine, sertraline, MDMA, etc... but that's a subject for a different day.
 
downwardsfromzero
#591 Posted : 2/4/2021 1:40:11 PM

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BongQuixote wrote:
downwardsfromzero wrote:
Some interesting points have come up here. Lately I was thinking about the magnesium residue from that reduction route as well. One way of cleaning up co-precipitated harmala freebase and magnesium hydroxide would be to wash the alkaloids out with ethanol.

I'm currently working on ascertaining if there is a difference in alkaloid profile between material which has been extracted using ascorbic acid and that which has had a less strongly reducing acid. Subjectively, harmala decoction with ascorbic acid seems to be more euphoric. I'll abstain from speculation at this point but the plan is to see whether there is a greater amount of THH present in the ascorbic acid brew.

There are a number of confounding factors in my experiential work that need to be taken into account first and the process of elimination will take several weeks.


Where I live I can't get 100% ethanol, but I assume methanol may work as well? Just gotta dry it!

Methanol is a good solvent for harmala alkaloids. If you were to use ethanol it wouldn't need to be dry, although drying it to a fair degree isn't too difficult if you have a decent distillation setup for getting to 95%. Mg(OH)2 is pretty insoluble in most things apart from acids and aqueous ammonia, although I can't comment on what would happen in the case of there being magnesium-harmala complexes.

I've found harmala hydrochlorides to be soluble in 70% ethanol (and they were still damp); when I've produced some harmala freebase do solubility tests with aqueous ethanol of various percentages.


Bong Quixote wrote:
Filtering rue is frustrating, that's for sure. I just want to throw it all out after 2 days of dripping liquid through t-shirts and coffee filters.
I, like many, have found the cotton wool plug in the neck of a large funnel to be more satisfactory by far than coffee filters. Drip time was reduced to 1½ days Laughing
Ora, lege, lege, lege, relege et labora

โ€œThere 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."
โ€• Jacques Bergier, quoting Fulcanelli
 
Brennendes Wasser
#592 Posted : 2/4/2021 2:39:44 PM

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Bong Quixote wrote:
Filtering rue is frustrating, that's for sure. I just want to throw it all out after 2 days of dripping liquid through t-shirts and coffee filters.


At what stage do you actually filter the Harmalas?

Its not even needed and you will still get the same giant yield from these seeds. These alkaloids are mostly present in the peel. So grinding seed material only makes things worse.

Just throw the WHOLE seeds into pH < 3 water and do 2 or even 3 cooks on them; 1 h 80-95 °C.

Combine in a big container and throw in NaOH until pH > 11 and wait for Alks to settle, then do decanting. Wash with excessive water (just refill with fresh water after decanting, let it settle, decant, repeat) until pH = 7-8.

No Manske, no filtering and freebase Harmalas in no time! Love
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
endlessness
#593 Posted : 2/4/2021 2:46:00 PM

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Brennendes Wasser wrote:


These alkaloids are mostly present in the peel.


Do you have a source for this?

It's been years since I explored this but I remember seeing conflicting information from different home experiments, sometimes yield of whole vs ground was equivalent, sometimes ground had significantly more..

There might have been some more recent investigation or more controlled experiments I missed, that answer this question better.
 
Jees
#594 Posted : 2/4/2021 7:56:39 PM

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Congrats with the pics BongQuixote Thumbs up Nice to have another looker on crystals.
It's not a sharp measuring tool, but it's something worth, seeing those shapes.
Harmine: seeing that there's some web between the needles, this could refer to slight harmaline contamination? Just asking. The harmaline looks good. Can't discern the globes on the THH picture, but if the harmaline is gone (which is clearly the case) then it can't really go else than THH I presume.

BongQuixote wrote:
...Harmaline: Like harmine, but 4 times stronger MAOI...
I've been searching a long time for articles about claims in that sense, if anyone has links to studies or so ...... you're very much appreciated Love





 
Loveall
#595 Posted : 2/4/2021 8:08:50 PM

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Hey Jees, have you seem the attached paper? I believe the conclusion is that Harmine and Harmaline have roughly equivalent MAO-A inhibition and the two compounds together are responsible for essentially 90% the inhibition from rue seed extracts.

Cheers.
โ€œ... (a) psychedelic substance occasionally causes psychotic behaviour in people who have not taken it.โ€
Excerpt from a McKenna talk transcript / audio.
 
GordoTEK
#596 Posted : 2/4/2021 8:51:44 PM

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endlessness wrote:
Brennendes Wasser wrote:


These alkaloids are mostly present in the peel.


Do you have a source for this?

It's been years since I explored this but I remember seeing conflicting information from different home experiments, sometimes yield of whole vs ground was equivalent, sometimes ground had significantly more..

There might have been some more recent investigation or more controlled experiments I missed, that answer this question better.



I had also heard from multiple people that it is much better to use whole seeds, less mess and clogged filters, and supposedly gives the same yield. Well I tried it, and yields were lower. Also tried other suggested things, such as doing several freeze thaw cycles on the whole seeds after soaking, and still yields were lower for me vs. grinding first. Also tried pressure cooking the whole seeds, that didn't help much if at all either. I don't have my notes handy at the momment so I can't tell you how much lower the yield was, but I think it was significant, maybe 30% lower? But filtering WAS a lot easier, so I could sort of see the argument for doing it that way even though yields will be lower, the seed is pretty cheap so just use more seed to start with...
 
Fruit is life
#597 Posted : 2/4/2021 9:11:21 PM

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I found no difference between grinding and the seeds and using them whole, that being said I usually run the whole seeds through 6-8x 1.5 hours boils, or run the rue "sock" through 3x2h 15psi pressure cooks. Filtering is alot easier and id rather spend the extra time boiling and then filtering.
The self that talks doesn't know, the self that knows doesn't talk.
 
GordoTEK
#598 Posted : 2/4/2021 9:32:44 PM

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Fruit is life wrote:
I found no difference between grinding and the seeds and using them whole, that being said I usually run the whole seeds through 6-8x 1.5 hours boils, or run the rue "sock" through 3x2h 15psi pressure cooks. Filtering is alot easier and id rather spend the extra time boiling and then filtering.


That makes sense, I did not boil as long as you did, and when I tried the pressure cook sock method I think I only did two, one hour cycles so perhaps your 3x 2h cycles would get the full yield. I do like the easier filtration a lot.
 
BongQuixote
#599 Posted : 2/4/2021 9:35:30 PM
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Jules_supertramp wrote:
Ah wouldn't be so sure about that buddyWut? ...there are plenty of records from people having had hypertensive crisis due to a wrong diet in combination with MAOI medication. Here is a interesting read: https://erowid.org/chemi...maois/maois_info2.shtml
Maybe that's why some people feel ill and need to vomit?

I think the vomiting is definitely harmaline, but that's just my experience.

Yes, MAOI medication can definitely cause issues combined with your diet. My point is that harmine is a weak MAOI, and reversible so short lasting, and therefore less likely to cause issues. From wikipedia:

Unlike MAOIs such as phenelzine, harmine is reversible and selective meaning it does not have nearly as high a risk for the "cheese syndrome" caused by consuming tyramine-containing foods, which is a risk associated with monoamine oxidase A inhibitors, but not monoamine oxidase B inhibitors.[11] Both MAO-A and MAO-B break down tyramine, but large doses of harmala alkaloids begin to affect MAO-B as well.
 
BongQuixote
#600 Posted : 2/4/2021 9:42:51 PM
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downwardsfromzero wrote:
I, like many, have found the cotton wool plug in the neck of a large funnel to be more satisfactory by far than coffee filters. Drip time was reduced to 1½ days Laughing

I figured it was much better to wait an additional day of filtering, considering I was out of cotton balls and I would haven taken at least 10 minutes to get to the store to pick some up. Smile
 
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