Clear citric water pulls turn dark brew as reduced

[modern]

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 cyan is the sulfate portion.

The ethanol that was precipitated contains harmalas based on 365nm light and will be evaporated (this is the golden brown top right) … the isopropanol is a very faint blue and yellow in color bottom right 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. this would confirm the brown cloudy precipitate is likely harman.

 

[modern]

So based on description these are harmine freebase crystals. Slender orthorhombic prisms. This is what precipitates from ethanol and isopropanol but fairly certain harmaline remains soluble. The camera doesn’t pick up how shiny the crystals are on my hand it shines like glitter.

Added hcl to see if precipitate would form and those yellow needle hcl and a cloudy somewhat amorphous precipitate. I’ll heat to recrystallize and see. May also be Harmine but strange that it remains soluble

The final photo is the dark golden crystals that formed from the brown cloudy precipitate that I suspect may be harman or something. The very deep blue is still evaporating.