Unsuccessful harmaline -> THH reduction

[Jagube]

I've performed two reductions now and I'm starting to believe they didn't work.

I never saw any blue glow in UV. It just seemed to turn 'dirty' and less green, but I'm not entirely sure and it wasn't an exact measurement and it may have been other factors (differences in lighting etc.)

Also from the few bioassays, I'm becoming more convinced that it was harmaline.

Perhaps the conversion was partial and not full. Even if it was a large part that converted (say half), could the green glow overpower the blue one?

I'm wondering if my zinc is to blame. It doesn't look like dust, it's much more coarse. Is there a safe way to grind it?

I can't think of anything else. Any suggestions welcome.

 

[Jees]

Harmine and THH are quite tasteless in opposite to harmaline which is very yeuck.
If you had a microscope you could check crystal form.
If you had TLC plates you could check the spots.

...Also from the few bioassays, I'm becoming more convinced that it was harmaline...

Can you elaborate this please?

It might be possible your zinc is too course, then just use longer times?
Or if the zinc got oxidized it would not work but then it would turn white.
Did you still smelled vinegar at the end? Or checked pH still being low?

 

[Jagube]

Should harmaline taste bitter in both freebase and salt form? From what I remember, all my harmala extractions and (presumably) separated harmine have tasted bitter in acetate form.

...Also from the few bioassays, I'm becoming more convinced that it was harmaline...

Can you elaborate this please?

The last time, which was the most evident, I took 100mg of the presumed THH, followed by 160mg of what I believed to be separated harmine, but may have had a considerable harmaline content. And an unknown amount of limonene-pulled MHRB extract (which in the end turned out weak, and resulted in essentially a harmala-only experience).

I didn't notice any quality not experienced with the various harmine/harmaline rue extracts I had tried.

However, I did experience a particular kind of lightheaded feeling, which seems to be characteristic of harmaline (but I'm not entirely sure... I feel it more with crude rue seeds than with extracts). And that lightheadedness was very strong. My explanation is that the 100mg of presumed THH was actually harmaline, which on top of the 160mg harmine/harmaline gave me a harmaline-heavy experience.

It might be possible your zinc is too course, then just use longer times?
Or if the zinc got oxidized it would not work but then it would turn white.
Did you still smelled vinegar at the end? Or checked pH still being low?

I could try longer times, but I have no idea how much longer it would have to be. Also, the harmaline was dissolved in HCl (bringing the pH to around 1.0), and that's supposed to make the reduction much faster than with vinegar. After a few hours the pH had crept up due to the stirring driving off the HCl gas, so I added vinegar and kept it stirring for another 18 hours.
The zinc wasn't white.
I can't remember the pH or vinegar smell, that's a good point to check next time, but wouldn't there still be vinegar in the case of a complete reduction, considering that we aim to use an excess just to make sure it's enough?

Another possibility is that the extremely low pH degraded the harmaline into something else (harmalol? harmol?), and that may be what gives me the strong lightheadedness in crude rue seeds.

 

[Jees]

Should harmaline taste bitter in both freebase and salt form? From what I remember, all my harmala extractions and (presumably) separated harmine have tasted bitter in acetate form....

I've not salted my separated products so far, they're all still freebase. I can't say how the separated alkaloids should taste in salt form, sorry.

For the rest you point out a lot of probabilities, possibilities ...

It's hard to nail THH in feeling when combined with other harmalas, the only definite thing to say is that the THH makes the experience prolonging, but then again harmaline does that also.

If you take say 50 mg (FB) of presumed THH one would hardly notice anything, but when it was harmaline it should be felt, not strong but felt nonetheless.