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Substitute for sodium and alcohol reaction?

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So harmine can be made into THH by disolving in alcohol and reacting with sodium. I'm not a chemist and I'd think that working with sodium is a bit dangerous even if less reactive in alcohol than water.

I was wondering if anyone would know of an alternative to this? Using salt and electrolysis? I have zero idea and am just wondering since this forum tried do the zinc reduction on harmine like is done with harmaline.


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Why you would like to go directly from harmine? In order to have a better total yield?

Makes sense to try get most out of your stuff, but as harmalas are so cheap why not just do 2x extractions and then also have 2x harmaline instead of using all harmalas with a dangerous reaction?

I guess sodium is super strong for reduction and thats why it works then obviously. So any alternative could be also similar strong reduction agents. I have heard of raney nickle being strong. But no idea if it might over-reduce. Also no idea if that stuff is maybe even as dangerous as sodium?
Ok so I did more research and Magnesium is also a strong reduction agent very close to sodium as far as potential.

I'll try to see if I can do a reduction using magnesium strips in 99+% isopropanol. Perhaps the use of vinegar doesn't allow provide enough energy but in pure alcohol it'll work? I dissolved some impure harmine and harmaline and added a few shavings of Mg ribbon. I'll follow any progress based on uv light.

As far as harmala costs... for me in Brasil caapi is 'cheap' and good source but rue seeds is not readily avaliable and very expensive when available. Importing is not worth it due to customs and heavy taxes.



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Sorry, but magnesium ribbon is not going to reduce harmine (at least I very strongly suspect not).
For any chance of a successful reduction using magnesium, you'd likely need to use fresh turnings and maybe even a completely inert atmosphere like argon. Unlike sodium oxide, magnesium oxide is not dissolved by alcohol. This oxide layer will prevent magnesium from reacting.

Another trick to try is adding a crystal of iodine to the magnesium when it's in the alcohol. Once the brown colour disappears from the solution you could add the harmine. [Iodine is also rather hard to get these days but not beyond the reach of sufficiently resourceful people who are prepared to go to some lengths to isolate it if necessary.]

Methanol is a better solvent than isopropanol for harmalas and may also be a bit better at providing protons to the reduction reaction. It all does boil down to availability of materials, of course.

Raney nickel was mentioned above, but use of pressurised hydrogen is rather an advanced technique and decidedly hazardous - besides the explosion risk of hydrogen, the catalyst itelf is pyrophoric. Urushibara nickel might be worth looking at for this reaction since it is all-round a friendlier material to prepare and work with. Its mode of preparation can be selected to optimise the type of reduction for which it will be used. That subject is its very own rabbit-hole but if you decide to look there you'd best search with the aim of reducing a substituted pyridine since β-carbolines are a bit niche.

This is all leading me to a logical conclusion that you might as well first of all try using your magnesium ribbon to reduce a harmine salt in acidic water. If that doesn't work, your next easiest option might be to crack open a lithium battery. Again, a significant degree more dangerous and with numerous additional caveats.
Yea the magnesium ribbon didn't react to the isopropanol. I left it for a few hours and nothing came of it... However when I heated it on a hot plate there did 'SEEM' to have some reaction but hard to tell if it was producing hydrogen or was acting as a boiling stone.

I'll try to do it again with a known starting weight and and add a little excess of magnesium ribbon. I'll heat again. The black light did change during the heating but seems to have returned. The dark faint blue is hard to tell even if I had it.

As for extracting I'll be doing the Ethyl Acetate Approach Harmala since I dont have ammonia and have EtAc on hand. I think it'll remove most of the magnesium.

This idea may fail completely. I'm not really going to go deep in the chemistry side and just thought it would be interesting... Lithium seems just as dangerous as sodium and if Mg failed I'll just abandon the idea.
So there was a change in color but I suspect it is due to the 'magnesium contamination' of the solution?

The harmine is no longer a shade a blue but greenish pretty close to unreacted harmaline. The harmaline is almost a highlighter yellow which is completely unexpected and I thought it would be the THH shade of a dark blue. So I'll try doing a micro EtAc extraction on the material check the end product.

Something did happen upon heating the isopropanol dissolved harmine and Mg ribbon cuts as did the other harmaline solution.
Yes, lime followed by EtOAc will remove practically all of the magnesium. To gauge the success of the reaction, other than with TLC, you can use the Van der Sypt protocol if you have a pH meter (although ammonia is the preferred base for that).

Do you have any ammonium salts to hand? You can make ammonia by mixing an ammonium salt with lime (in the appropriate apparatus, of course). If you have ammonia and phosphoric acid separating magnesium salt from harmalas is really easy.

Your report of a colour change is intriguing. Presumably you are referring to the fluorescence. If so, this would be a tantalising hint that you may have performed the first conversion of harmine to harmaline that I've ever heard of. It is unwise to make assumptions in the absence of a confirmatory analysis, however. Once more, was this magnesium and harmine freebase in anhydrous IPA? How about cleaning the Mg ribbon with fine grit sandpaper immediately before adding to the reacting?
This was the first attempt I did just to test the idea. I finished extracting and cleaning up some harmine and harmaline to reattempt even if I fail its fine.

I didn't sand the MG ribbon this first time and there was zero reaction once adding to the anhydrous IPA.

From my understanding you can't convert harmine to harmaline directly.

So the alcohol had dissolved harmine freebase. It would show the fluorescence is that blue tone it has correctly. I then placed the MG ribbon cut up and expected there to be so sort of bubbling but NOTHING happened for hours. So I then heated up the alcohol on a hotplate and there was indeed a reaction.

Mg and isopropanol can be used to redox producing Mg hydroxide and propane. HOWEVER based on what I could find it cannot place 4H+ and can only do 2H+ so not possible to do harmine to thh.

I will be reattempting sanding the Mg ribbon and then heating it like I did. I also did this to the harmaline and the color was NOT the dark blue which I expected and became almost a highlighter yellow fluorescence. IDK what happened there.

The large beaker is harmaline acetate before basing. The small beaker on the left is the reacted harmine after heating iso and Mg to evaporating then adding vinegar. The Mg completely dissolved afterwords. The beaker to the right is harmaline with the same process.


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Yes, I'd be very surprised if magnesium really did reduce harmine. There are all sorts of possible side reactions that could occur, like dimerisation for example. The fluorescence is also pH-dependent so the production of magnesium isopropoxide could have led to this change in fluorescence by making the environment more basic.

Are you absolutely sure that magnesium reacts with IPA to produce MgO and propane? I would have thought it far more likely that the products would be magnesium isopropoxide and hydrogen.

Adding 4H (not just H+) would occur as a sequence of additions of electrons and protons to the harmine. The intermediate radical states are what could lead to dimerisation reactions. This can be controlled to an extent by keeping the harmine concentration low.
I don't have any idea the actually reaction mg and ipa. One source said propane others say h with different products.

I'll be trying to repeat this with my very clean extracts again. I'll measure a starting weight just to have something and then proceed to go all the way thru to using EtAc to remove and shine black light again.
modern said:
I don't have any idea the actually reaction mg and ipa. One source said propane others say h with different products.

I'll be trying to repeat this with my very clean extracts again. I'll measure a starting weight just to have something and then proceed to go all the way thru to using EtAc to remove and shine black light again.
How's the experimentation going?

Do you have a reference for the claim about Mg + ipa → MgO + propane?
I asked an ai chat bot lol. Here is what it prompted
"When isopropanol (also known as isopropyl alcogol) reacts with magnesium, it undergoes a combustion reaction. The balanced chemical equation for this reaction is:

2 Mg + C3H8O (isopropanol) >> 2 MgO (magnesium oxide) + C3H6(propene)

So, in addition to magnesium hydroxide (Mg(OH)2), the reaction also produces magnesium oxide (MgO) and propene (C3H6). However it's important to note that the reaction is highly exothermic and can be dangerous if not conducted properly. It should only be preformed under appropriate laboratory conditions by trained individuals."

So it is propene not propane liek I mentioned. Also maybe this is wrong since gave a few different prompts to me after you mentioned it.

I gave this a pause to work on my salty tea extraction. I have the harmine and harmaline/thh powders saved for playing around with this again later.
Sorry, but "AI" (machine "learning") chatbots are notoriously bad at chemistry! :lol: It's almost at the level of "not even wrong" by suggesting that Mg plus isopropanol makes a "combustion reaction" where one of the products is propene. This is a great illustration of how a generative chat algorithm has no comprehension of what it's saying.

They overuse the phrase "it's important to note" to a hugely annoying level as well.

Did it even reproduce the common typo of "preformed" instead of "performed"? That's also fairly poor :x

Methods do exist for converting alcohols to alkanes but I've not seen any that are as simple as heating the alcohol with magnesium ribbon, and that's a method which really makes one think it would have been noticed by now if it actually worked.

Fortunately it's easy to distinguish between propane and hydrogen by simply setting fire to a small sample of the gas collected in a test tube. The isopropanol might mess this up a bit though.
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