Reducing harmaline to THH?

[AwesomeUsername]

I've seen this mentioned in another thread.

However the question was about something else, it was only reported that harmaline has been reduced to THH, thus it contained another florescent color/shade.

The idea that it can be done is interesting, thus my question. How would that work?

I am not particularly skilled as a chemist but I know the basics.

Harmaline has one more hydrogen atom then harmine, THH should have more then both, but how much more?

An theory from my side is that this could be achieved with the help of an alkaline compound, or maybe heat as well, but I don't know.

Anybody with more knowledge?

I would also be interested is harmaline can conver to harmine somehow.

 

[downwardsfromzero]

Harmaline has two more hydrogen atoms than harmine, and THH has two more than harmaline. Hence the name, tetrahydroharmine - THH. Harmine can indeed be formed by dehydrogenation of harmaline - or, of course, of THH, except THH is maybe too precious for that if you've gone to the trouble of hydrogenating harmaline to make it in the first place.

Your requisite proper chemistry lesson will have to wait until tomorrow morning; suffice to say, changes in pH are not the way these (or any) compounds get hydrogenated.

 

[merkin]

There is a relatively simple tek and plenty info on Nexus on how to reduce HarmALINE (DHH) to THH via a zinc reduction. Gordotek also made a video once of the process that you can find via google I'm sure. You can apparently use magnesium instead of zinc but I have not tried that route. I do not know of any method to THH via Harmine.

Understanding the 'VDS protocol' regarding the accurate pH separation of Harmine/Harmaline is pretty useful as well, a far superior method to the standard Nexus Rue tek versions - it uses dilute Ammonia as the base and is a good idea when you come to precip your THH freebase from your zinc reduction. There is a soopalong thread all about that on Nexus but great to read and absorb if you are serious about exploring the Harmalas!

 

[downwardsfromzero]

The classic reduction of harmine to THH uses metallic sodium dissolving in amyl alcohol (1-pentanol). This is a dissolving metal just like the zinc or magnesium reduction of DHH; sodium is a more powerful reductant - it's reactive enough to bring about this "hydrogenation".

The idea of "nascent hydrogen" (an extra-reactive form of hydrogen - monatomic? electronically excited diatomic? both? something else?...) has been postulated and discussed for well over a century. Based on the current evidence, what is actually thought to happen in these cases is that the dissolving metal gives up electrons to the surrounding medium. Some of these get captured by DHH molecules to form a radical anion, which rapidly captures a proton, H⊕, to complete the first phase of the reduction (and which incidentally, illustrates the equivalence of gaining an electron and adding a neutral atom of hydrogen).

"But that's only one atom of hydrogen!" I hear you say. Well - you're quite right, the process gets repeated - accepting an electron to form a radical anion, followed by protonation. Then we have formed our THH from DHH. In the case of harmine - plain ol' H (careful!) - a grand total of, of course, four electrons must be added to the molecule, along with the corresponding four protons which jump aboard - TetraHydroHarmine. THH.