Hello everyone I'm quite new to the forum but not quite new to this world. Been a lurker for a while.

I have some knowledge in chemistry and I'm going to academically study more of it in the next years.

A week ago I decided to try an extraction of Rue (following the tao) for the first time and after some initial complications I managed to understand some of what I was doing.

So where I am now I almost finished with the extraction and from a 200mg starting material in seeds I already harvested 4g or alkaloid of variable purity from different pulls.

Coming to what I think is my last pull something weird happened:
I had a manske sitting in the fridge for 3 days and after filtering out 2/3 of the precipitation and basifying it I kept a third for a second pull (that for some reason is always more profittable than the first).
So after redissolving the alkaloids and reducing sligthly the solution the only precipitation I got was salt in a reddish liquid.

Where my alkaloids went?
I tried to add some more vinegar to dilute the solution that was obviously supersaturated but I didn't obtain any precipitation but just reddish solution.
After more reduction obviously I have salt again.
Is it possible that through all my pulls it is now too acidic to precipitate?

What could I do?
Would it be a good idea to basify it with Sodium Carbonate to have freebase precipitation even tho I have lot of salt in it?

Thank you everyone

this is how it looks in the pot after reducing it with salt crystals on the top:

Unsure what has happened there. Did you use water to dissolve the Harmala Hcl the second time round or vinegar?

You could add minimal water, to redissolve salt. Then basify with sodium carbonate. Settle and decant away the salt water (might be worth keeping just til yield is checked), wash with cold water, allow to settle, decant away this water. Restart mansking.

I used 10% vinegar, as reading on the forum in a topic was suggested to dilute directly with vinegar.
Was it a wrong move? and if yes why?

Anyway if I basify I would keep the freebase.

Thanks!