Very interesting result, ShadedSelf. You should consider checking it with TLC. It may be time for me to try this putative reduction myself.


Also worthy of note is my current thinking that ascorbic acid may conserve harm(al)ol in the brews as much as doing anything else. I will nonetheless try simmering purified harmaline with a concentrated solution of ascorbic acid sometime, however.

The figures for reduction potential still need looking into - any other takers for a bit of chemical arithmetic? There's a few other things I ought to do first...

I dont have any TLCs, but I could probably tell you if there is any THH in there just by looking the freebased alkaloids.

How would one retrieve the alkaloids from here?

Are you planning to use microscopy? You can watch the crystal formation after adding ammonia to a drop of the alk solution on a microscope slide - there was a thread about this, or maybe it was in the VDS protocol thread.

The VDS protocol thread details how you can recover the alkaloids separately.

I was more concerned with H2O2 reacting with particular bases.
Souns like ammonia is safe.

No mycroscopy, in my experience harmine forms a brownish, fluffy powder, THH a white and dense one.
Assuming there is just one or the other in there should be easy to tell.

Ive based the solution with ammonia, havent dried it yet but all I see are small brown needles, pretty sure there is mostly just harmine in there.
Not very scientific, but the best I can offer right now.

In my experience, pure enough harmine can also be white and fluffy. There are some "impurities" (by impurity I refer to everything aside from harmine, harmaline and THH) which fall out at lower pH, so the brownish color of harmine is likely because of that. To assess properly, you should separate harmine and harmaline, do further Manske on them separately (or even freebase recrystallization with IPA if you will), and then basify and check the texture. In my experience, freebase THH doesn't differ that significantly from harmine and harmaline, but THH-HCl is quite different, it doesn't form long sharp needles or fluffy hair-like structures but more like... the flora at the see-bed. Also, the texture is more brittle.

Thanks for the input.

I assumed little to no impurities, the starting material was fairly clean.

I acidified the alkaloids and added a bit of NaCl, white crystals started to form.
I know Harmine and DHH HCL together form golden needles, and looking for images of their HCL salts separately does seems to indicate that both have that golden color individually.
THH HCL forms in small white crystals IME, so looks like it its THH after all.

The manske filtrate had a red color to it and upon basifying a bit of dark brown/reddish stuff started to precipitate, no idea what this is or where it came from.

Really late here but this might be true.

Recently I did just that.

Cooked for a really long time with some citric acid, left it to stay, cooked again, filtered the seeds, reduced everything to a syrup, pulled with ethanol and it was a huge difference.

It didn't feel dirty, sludgy and like something was off and wrong.

It turned my mood from annoyed, and exhausted to relieved, carefree and almost euphoric.

Never had a huge dose of harmalas on their own or tried pure THH, but the feeling made me think a big part converted to THH, it truly felt like a bliss.

My preference is to keep harmalas on the low side, to prevent feeling sick, but even at low doses, no bodyload what so ever yet a significant mood boost. Changed my opinion on rue seeds after just a single dose. Would recommend to anyone to try it, although the preparation was messy, long and all over the place, it was well worth it.