I believe I have successfully reduced Harmaline to THH with the help of the great folks here at the Nexus-- special thanks to Endlessness and Tregar.

The good news here for Nexians is that I am not a chemist, so I think the process is suitably easy and safe for most here to try. Of course, safety practices such as protective eye-wear need to be followed, as a strong acid is used. Also note that the reaction releases hydrogen gas, so you will want to ventilate properly.

I will also say that I messed up a bit, adding too much HCl solution at the start, which necessitated much more ammonia to basify than would typically be needed. I also have questions for the more experienced folks out there that I will type in orange because of the season.

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I began with 3g of harmaline, which was separated out of a clean rue freebase using sodium bicarbonate two times, to get it reasonably free of harmine.
Harmalas Extraction and Separation Guide

- I dissolved the 3g harmaline in 60ml of 32% HCl and 140ml of distilled water (200ml total). The solution had to be heated in a water bath and mixed for a while (5 minutes) in order for the harmaline to dissolve into a clear yellow solution. I think this is much more acid than should have been used, but would like confirmation of this. I did some back of the envelope calcs and think I should have only used about 36ml of the HCl.) Also, I'm surprised it was so hard to get the harmaline to dissolve-- would appreciate an insight

- While keeping the vessel at near boiling temp in a water heat bath, 12g of zinc dust was added a pinch at a time. There was a lot of fizzing and bubbling, and I would mix after each addition of zinc. I ended up using an additional 50ml of water to wash residue back into solution during the process.

- Kept stirring over the next hour, while the zinc fizzed away and danced in the solution (very fun to watch for a non-chemist, btw). At the end, the solution had gone nearly clear, with just a slight tint of yellow-green.

- Stirred in 40g of Ammonium Chloride in the still heated solution (AniMed for horses, cows and such, easy to find in the US). As I added the salt, something kept wanting to fall out of the solution. I added another 150 ml of water and kept stirring until it all remained dissolved (total solution volume now 400ml). Was this the THH or was it zinc chloride? Did I need to add the water or should I have just filtered the stuff out? I feel like this was a lot of solution for a just 3g of starting material.

- Ran through a filter (very little zinc remained, which is not surprising, given the excess of HCl). The solution was then basified with a F-ton of ammonia-- at least 700ml (I used ph papers to confirm I was getting the ph I needed). The resulting THH then quickly fell out of solution.

I wanted to test if this is really THH, but lacking any serious analytical equipment, I decided to use the melting point of THH (190C); harmaline has a melting point of 234C. I put 120mg in the oven and heated to 405 degrees f (207C). After 10 minutes nothing seemed to happen, so I raised the temp to 415 degrees f (213c).

Within minutes the color darkened, and I pulled it from the oven and scraped it from the dish it was in. It had a tar-like consistency that quickly hardened when cooled. It also had reduced in mass from 120mg to 100mg. I took this as confirmation that the reduction was at least a partial success, though I don't know the percentage of conversion.

The (assumed) THH has virtually no taste, with only a little lingering bitterness. Some have reported a metallic taste but I find none. I think this suggests little to no zinc salt contamination.

The resulting 2.5g of end product is in the first pic. The second pic is the result after heating (melting) in the oven to test the melting point.

Ah, found an answer to one of my concerns. My ammonia was waaay to weak a concentration. I was using regular consumer stuff (3% concentration). I could have used one tenth that amount with the janitorial grade (30%). That would have matched the concentration of HCl. Lesson learned.

Took 35mg sublingually 30 minutes ago, and yes, it is active.

Thank you very much for sharing your experiment and results!

You could test with TLC, that would be an easy way to tell if it worked as well as for checking your harmaline separation.

Great... now I'm going to have a new obsession: discovering what plants of New England have tryptamines. lol.

Kit ordered. You may see me in the TLC forum asking for help.

Just a thing, but why (oh why oh why!) did you put the entirety of the product into the oven when a small sample would have sufficed? Now you have a blob of charred crap that may only be active from partial reconversion to harmaline.
Edit: I just re-read the thread title

Other than that, well done, and what endlessness said^!

Oh heavens no! I only put 120mg out of the 2.5g of (hopeful) THH in the oven. Little brain- yes. But some brain.

I should have the Bunk Police test kit here in a couple days btw. Can't wait to post the results, positive or negative.

Feel free to ask him if you have any doubts once it does arrive if you run a plate with your harmala samples next to your thh sample it should be pretty easy to spot, check this out:

https://www.dmt-nexus.me...aspx?g=posts&t=35984

Phew! Thank goodness! There's some really dense people in my neighbourhood (myself included perhaps ), I think my perspective may be a little skewed...

Looking forward to seeing the TLC results.

Ah, thank you Endlessness. Have the TLC kit on order and expect it in a couple days. There was no direct mention of THH (not surprising), so I am grateful for the link provided.

Does the spotting light offer different UV frequencies? I guess I should move that question to the other sub-forum.

Unfortunately, I'm fresh out of Caapi extract, and too eager to wait to make some more. I can, however, run my separated Harmaline and Harmine along with the THH.

The light that comes with the kit is 254nm (short wave)... 365nm is a normal black light frequency, you can for sure easily find it elsewhere if you are interested. I have one at home from lighthouse , but I bet you can find cheaper elsewhere. In any case its not necessary to have the 365nm one, its just an extra thing to experiment with but with the 254 it should be enough

TLC Analysis is in-- see the pic below. The plate has just dried, and is being viewed under a 254nm lamp. I can post the 24 hour result tonight.

I will have to depend on others to let me know what is going on here, but here are my observations...

- The strong blue of the top row of dots correlates with Harmine in the previous TLC analysis by Endlessness (surprised by the amount of it across all samples). This is interesting because when I separated the harmalas by ph, I was left with a lot more 'harmaline' -- but perhaps I was just not adequately separating out enough of the harmine, leaving a fair amount of it in each sample.

- The lower light-blue dot correlates to Harmaline

- The color at the center of the Harmaline sample lower dot is a bit more yellow than the lowest dot in the THH? sample. The outside of the circle (light blue) is similar to the harmaline.

- The lowest dot of the THH? sample is a greyish blue; just above it is a faint patch of light blue matching the harmaline.

If I were to guess what is going over here is that all samples have a fair amount of harmine. Also, there are two separate compounds in the THH? sample: a small amount of harmaline and (I hope) THH.

Looking forward to having more educated eyes look at this....

I would agree, it looks like your 'mostly harmine' is quite clean, that your reduction from harmaline to THH was near complete, and that your harmaline and THH have a buttload of harmine in
THH acts a lot like harmaline in terms of pH, it bases at just a little higher pH than harmaline. So the separation trick used for harmine/harmaline will work for your harmine/THH. Just dont go too overboard on the baking soda.
If I were to do that separation, after removing the harmine with baking soda I'd heat up the solution, keep it warm for a while [coffee maker hotplate works], and then add the sodium carbonate. Baking soda decomposes in hot water, bringing its pH higher. [This is why, in harmine/harmaline separations, one should always dissolve the baking soda into cool or room temp solutions.]

Thanks Auxin--

Looking forward to more giving input, but I feel pretty good that the THH conversion seemed to go so well. ... just my harmaline/harmine separation needs some work. I think the problem is that I was using papers rather than a proper ph meter. It may be worth the investment to get one.

Thanks for the tips on separating the THH from harmine. I may keep them together, as I like their affect as a duo (especially with dmt pharma). THen again, since I don't know the actual mix, separating them will give me an opportunity to explore a range of mixes.

The Bunk Police TLC kit is awesome, btw. Very easy to use.

Awesome to see you testing this

And yeah your interpretation is correct, you have mostly harmine, then harmine plus harmaline, and then harmine plus thh (and maybe a tiny bit of unconverted harmaline)

Yes Nitegazer, lots of words on THH but few really digging in.

Yay! So glad to have contributed a bit. I will have to run the reduction again with purer harmaline, a bit less HCl, and more concentrated ammonia.

The low cost and ease of running the reduction makes it a viable alternative to caapi extraction. Jees and others have been finding ways to reduce the time and trouble of extracting rue. Rue is cheap and has a 6% yeild. 100g of rue can result in 3 times as much harmine/THH as a caapi extraction-- well worth the extra steps of the reduction imo.

And there was one side discovery: melting point differentials can not be exploited to separate THH from harmaline-- when melting, THH degrades considerably.

thank you for this, Nitegazer and please continue....