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Clear citric water pulls turn dark brew as reduced

I added hcl and dry ethanol to the brown precipitate and it formed dirty gold crystals and the color of the alcohol is now a very dark blue color. Not as traditional blue but darker. The larger blue color is actually cyan in person.

The ethanol that was precipitated contains harmalas based on 365nm light and will be evaporated… the isopropanol is a very faint blue and yellow in normal light has precipitated needles and I think even cleaner… I think the alcohols are able to partition the harmalas?

Once the small blue fraction evaporates I’ll try to see if it sublimes at 120-130c. This was that cloudy brown precipitate that forms.
 

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