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Harmaline reduction with magnesium powder

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Jan e Kharabat

Jan e Kharabat

Established member
So, I tried to reduce harmaline with magnesium powder (didn't have the ribbon at the moment). I used about 2.7g of harmaline dissolved in 150ml acetic acid and around 900mg of magnesium powder. The reaction was quite fast and violent with a very rapid release of hydrogen. The powder remained stuck on the surface and would not sink down like zinc powder even upon stirring. The beaker became somewhat hot, but not too much. After a while the reaction stopped, but some magnesium powder was still left. Upon adding more acetic acid the reaction continued again. I also noticed some dark brown colored particles floating on the surface. I collected them with my stirring rod and found that they were quite sticky.

After a few minutes, the solution changed its color and became lighter, but the fluorescence was still green, same as before. Somehow, the magnesium reacted with acetic acid while leaving the harmaline unchanged. The change in color was likely due to the increased concentration of magnesium salts. After filtering I basified with ammonia, no clouding occurred up until pH 8.5 or so (don't exactly remember, but definitely above 8 ). Despite the clouding, nothing precipitated until pH 10 or so. I brought the pH to 10.7, the clouding stopped and the precipitate particles were very fine. I filtered and dried the precipitate and could clearly tell... there was a shit load of magnesium stuff in there (magnesium hydroxide?). The precipitate was very "cakey" and had a gelatinous texture. I will perform Manske and see what happens.

In any case, it can be concluded that the mere color change is not an indicator of successful reduction, the fluorescence has to become blue as well. Also, that the concentration of metal salts likely effects when and how the precipitation occurs.

Feedback and suggestions, specially from folks who know a bit of chemistry are very welcomed and much appreciated.
 
What particle size was your magnesium powder? It sounds like it was rather on the fine side from the speed and heat of the reaction. I would suggest trying to use coarser material such as granules, or add the magnesium more slowly. The point of a dissolving metal reaction is to get electrons transferred from the metal onto the harmaline molecules (in this instance). Any gaseous hydrogen formation is a waste.

This is only my opinion here, but I feel that with magnesium it's important to keep the reaction rate down by using low acid concentration and keeping the temperature down, as well as the aforementioned use of coarser magnesium particles. The harmaline has to be able to come into contact with the metal so if it can't diffuse there quickly enough the water will be reduced instead.

There was an earlier thread where someone claimed to have had success in a magnesium harmaline reduction, we'll have to see if we can dig it out. Meanwhile, I have plans to test this out a bit more, so - hopefully - before too long we'll have a bit more to discuss.

Until then I'd strongly suggest getting hold of magnesium ribbon, granules or even a bar or ingot from which you can make turnings.
 
Yes it was a very fine powder, I will get the ribbon next. It has been suggested that excess ammonia can re-disolve the metal salts but I think that only works as long as the salt concentration remains below a certain point. In another experiment, I used zinc but let it react for too long and as a result the zinc salts precipitated along with the THH.
 
I posted on this in the VDS thread here: Harmine, harmaline and THH from Syrian Rue. Verification and finetuning of the VDS-protocols - Collaborative Research Project - Welcome to the DMT-Nexus

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Hi, read this entire thread and decided to do a magnesium reduction using acetic acid. I've tried zinc reductions before, and the only time I got decent results was using a test tube and swirling it manually for about 3 days.

Added 5g Mg ribbon to 150ml 7% acetic acid with 3000mg harmaline FB dissolved in a flask. I know this is an excessive amount of Mg, but I wanted to make sure I had enough to complete the reduction. Magnetic stirred on low speed for about one hour, plenty of bubbling. The bubbling suddenly slowed down and almost stopped, while there was still plenty of Mg ribbon left. I added more acetic acid, and the bubbling started again. Stirred for another hour, bubbling stopped and I left it for an hour. Filtered out the remaining Mg and measured PH at 4.8. Solution started with PH around 3.5 before reduction. The acetic acid reacted with the Mg, creating magnesium acetate and hydrogen, consuming itself in the process.

Based dropwise with ammonia 12% and got a nice clean precipitate, filtered and washed with ammonia 3% to make sure all magnesium acetate would dissolve. Dried and ended up with almost 4000mg of white powder. There is some Magnesium contamination in there, and I wonder if I should have kept washing it. Maybe water's ability to dissolve magnesium acetate is limited and I needed more liquid to fully get rid of it. Or there was some additional reaction between the THH and Mg, not sure. Anyway, the product is great and the reduction must have been close to 100%. We did toxicity testing by trying small amounts, and have used it in sessions several times with no bad side effects. Magnesium acetate is basically non-toxic, and you would need something like 861 grams of it for an LD50 dose, and the amount in a standard 200mg dose is around 50mg, so not too concerned. However, next time I will use more liquid and less Mg and calculate my moles.

I can tell the reduction is good, since I get no harmaline effects, no tracers, no ringing in the ears, no nausea. With my zinc reduction attempts I always ended up with some unreduced harmaline, which is easy to spot during consumption.
 
Here's a footnote about use of magnesium ribbon with plain Syrian rue tea.

In summary, it seems that this is likely to be a waste of time but another replication is necessary. I think making the effort to crash the alkaloids with one basing before redissolving and performing the reduction. There are still a few confounding factors to eliminate, which I shall note below.

Crude UV results only show the bright glow of harmaline. Granted, that masked just about anything even at all but the lowest concentration but I've developed an eye for how the fluorescence varies with decreasing harmaline concentration. The UV penetrates further into the solution at lower concentrations on account of the lesser absorption, but in this case the UV penetration was pretty much the same as at the start of the experiment.

The confounding factors are that the reduction was carried out in a stainless steel saucepan and heat was applied. Another thing was the presence of ascorbic acid in the solution. Ascorbic acid can act as an electron acceptor and gets reduced to gluconic acid. Whatever may have happened, the reaction generated a large amount of black precipitate but fortunately this was easy to filter out using a cotton plug.


The difficulty of separating magnesium from the THH is something I've mentioned before, as is the potential problem of consuming magnesium-reduced tea without a purification step. Soluble magnesium salts typically have a laxative effect, so it's a good idea to isolate the alkaloids. As far as I can tell, the best way of locking up the magnesium is to use phosphate and ammonia to produce decidedly insoluble magnesium ammonium phosphate. It should be possible to dissolve freebase harmala alkaloids out of a MAP matrix simply enough using acetic acid. Otherwise the recent progress with ethyl acetate looks promising in this respect.
 
Been reading your post Dasein, downwardsfromzero, Bongquixote. Excellent post, thanks for sharing.

Thought would share, as this can be done "over the counter" without any fancy chemistry lab ware except for a plain stir mantel, which retails very cheaply.

A way to make pure tetrahydroharmine, Someone, author of the essential DMT guide asked me if I could post this in the "dmt allies extraction section", thought would link as it is not in the harmalas section:


The more zinc you use, the faster the reaction progresses, so 35 to 40g zinc means the reaction is finished by 1.5 hour.

I've looked at the #101 filter after filtration, hardly anything at all on it, truly only 1% of the zinc dust remains to be filtered after sitting for 1 hour.

If you don't have a vacuum pump/filtration setup: Personally, I believe the cotton ball in a funnel to be one of the greatest inventions of all time--and think it would work just fine for filtering out the remaining 1% zinc dust, remember 99% of the zinc dust falls to the bottom already after sitting for 1 hour after the spin mantel is turned off. What you are filtering is actually the 1% of zinc dust from the very bottom after sitting that get's kicked up back into the solution as you are decanting it off.

Homo Trypens (10.21.2021) recently posted that he had success using the method, even though he did not seperate the harmaline from the harmine, he used a full spectrum extract. So it appears the THH he created contained a mixture of THH + harmine, see post #285:

 
BongQuixote said:
I posted on this in the VDS thread here: Harmine, harmaline and THH from Syrian Rue. Verification and finetuning of the VDS-protocols - Collaborative Research Project - Welcome to the DMT-Nexus

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Hi, read this entire thread and decided to do a magnesium reduction using acetic acid. I've tried zinc reductions before, and the only time I got decent results was using a test tube and swirling it manually for about 3 days.
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Click to expand...

Great to hear! I'm going to do a similar try on a mixed harmalas extraction from rue. Have magnesium ribbon. But I'd like to minimize the magnesium salt for consumption and hope there is a way for this (hopefully without more chemicals like ethyl acetate).
 
downwardsfromzero said:
The difficulty of separating magnesium from the THH is something I've mentioned before, as is the potential problem of consuming magnesium-reduced tea without a purification step. Soluble magnesium salts typically have a laxative effect, so it's a good idea to isolate the alkaloids. As far as I can tell, the best way of locking up the magnesium is to use phosphate and ammonia to produce decidedly insoluble magnesium ammonium phosphate. It should be possible to dissolve freebase harmala alkaloids out of a MAP matrix simply enough using acetic acid. Otherwise the recent progress with ethyl acetate looks promising in this respect.
Click to expand...
I have tried the magnesium ammonium phosphate precipitation and it occurs at a low enough pH to be of utility in separating magnesium salts from at least the harmaline and THH. Harmine seems to co-precipitate at the end of the MAP fraction although a larger-scale extraction might provide better separation than this 5g rue seed brew test did. Harmine seems to wash out of the MAP well enough with a bit of ethanol, however.

I still need to check the solubility of MAP in acetic acid, maybe in dilute (~5%) AA it will be slow or limited enough to be useful for harmine recovery.
 
I said:
I still need to check the solubility of MAP in acetic acid, maybe in dilute (~5%) AA it will be slow or limited enough to be useful for harmine recovery.
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OK, checked this a few days ago and 0.1g of the putative MAP dissolves easily in 6mL of 4% AA. The spy pen shows slight glow of harmaline contamination but no harmine. [EDIT: I was going to point out that AA therefore appears to be of little use in separating any harmine remnants from MAP, but that I also still need to check out boiling of the MAP powder in order to make it more crystalline and then see if the crystalline material is any less soluble in AA.]

I'm starting to wonder why there seems to be so little harmine in this test.

Has anyone else tried a magnesium reduction on mixed harmala alkaloids and attempted to quantify 'before' and 'after' values for harmine?
 
downwardsfromzero said:
I said:
Has anyone else tried a magnesium reduction on mixed harmala alkaloids and attempted to quantify 'before' and 'after' values for harmine?
Click to expand...

I don't know, but I would also be interested in that. But by doing a magnesium reduction on pure harmine, one would get an idea. If not anything different happens when there is both harmine and Harmaline present in the reduction.
Click to expand...
 
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