During salt precipitation, swims harmala alkaloids didn't precipitate.

simmered in citric acid for 45 minutes,
added 100 g salt per liter of solution.
Refrigerated overnight.

Nothing precipitated.


What went wrong, and what can swim do to fix it.

How much harmala did you use?

How much citric acid?

What temperature did you subject it to?

1 lbs syrian rue seeds.
100 grams citric acid,
It was never boiled hard.
It was just simmered for 45 minutes.

Hmmmmm i think you went a bit hard there on the citric acid.I wonder if there is an equilibrium of some sort of the harmala turning into HCl form (from the salt) and the original acid used salt form. Some say that using different acids might take different times for harmala's to precipitate.

My proposition for the moment : heat up the solution,add more salt till more does not dissolve (make sure your solution is SATURATED) and then put to freezer for some time...It might take more than overnight.