So I was doing some reading about harmala conversions and found this page on erowid.

This caught my attention: Harmaline or harmine can be converted into tetrahydroharmine by reduction of either in an alcoholic solution by the action of sodium.

Being as elemental sodium is pretty dangerous and hard to get your hands on, I started looking for other reduction agents and came upon lithium. Here is a video on how to obtain lithium from an energizer battery.* BE CAREFUL, DON'T ATTEMPT WITHOUT PROPER SAFETY GEAR/VENTILATION *

So I came upon something called a Birch Reduction, which initially used sodium, but later was discovered to work more efficiently with lithium. I don't think the birch reaction will work for our purposes: "This reaction is quite unlike catalytic hydrogenation, which usually reduces the aromatic ring all the way to a cyclohexane." - which i think is what we are looking for, a complete reduction of the aromatic ring to form THH. It is an example of a redox reaction using lithium in place of sodium however.

I posted this in the advanced chemistry section with the hopes that some more knowledgeable members could comment as to whether or not this would be possible or even safe. I didn't want to post it in the harmala section and get people messing around with the idea before we even know if it is safe/possible to do at home.

So, could lithium be employed as a replacement for sodium to reduce harmine/harmaline to THH, and if so - how would one go about doing this safely?

Thanks! Hope I'm not way out in left field on this.

As far as 'safety' is concerned Li is not the safest thing with non-polars. This would be similar to what is done with the shake-and-bake method of methamphetamine if I am understanding this correctly... Which has lead to a lot of house fires and explosions because of inexperienced and unknowledgeable hands/heads.

I have yet to find a method for saturating harmine to harmaline. If anyone can pull up any references it would be very interesting to entertain this idea.

Electrochemistry seems like a viable route, although experimentation would need to be done first. Something I plan on doing in the future(once there is money to invest in lead electrodes, etc).

lithium certainly has the reduction potential to do it (zinc is too weak)
but your reaction system has to absolutely dry, devoid of any moisture.

so how could it be done?

Use an absolutely bone-dry solvent. Distill it twice, dry it over a proper drying agent. Distill it and dry it again, why not. Oven dry glass-ware(12 hours use a conical flask) or under a strong flame. Turn on the dehumidifier if the room has lots of moisture. You will need a drying tube filled with anhydrous CaCl2(remember your air has moisture in it). I believe you can stain CaCl2 with CoCl2(TOXIC) so when moist the color changes and you can have some warning that your drying tube is becoming wet. Lithium metal must be stored in something such as paraffin or mineral oil.

Failure to completely dry this system will likely result in your non-polar igniting due to the highly exothermic reaction of Lithium and water. Li + H2O -> LiOH.

http://www.youtube.com/watch?v=8ypUVpwgcAA
This is what happens when lithium is placed on water.