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.

 

[modern]

so after the precipitate that formed those nice crystals I added hcl to the ethanol since no more precipitate was forming even after volume reduced by half. I got those needles and cloudy precipitate in previous post… after heating and cooling nice golden green needles formed.

I decided to add hcl to the first crystals and got a very white needle completely different from the greenish needles.

The original ethanol is still being evaporated since in theory only 2/3 the mass of the starting crystals have precipitate even with some losses. Starting 1g around 600mg+ precipitated maybe another 200-300mg may still form. Maybe those last but are impurities?

The last two photos is still the Freebase precipitate the top crystal and 335mg weight.

I didn’t take photo of the white hcl needles but nothing special just white and fluffy.

I plan to try to precipitate via careful ph to test what each is. I tried to see if I got the green uv color but both blue however wasn’t acetate so maybe that is why.

 

[modern]

So carefully adding lye drop by drop at ph 7.5-8 the creamy precipitate remained after stirring and started to settle on the bottom.

The beautiful crystals formed completely white precipitate white the green gold hcl formed some off white crystals so likely was a mix or just “inferior” crystals.

The remaining unprecipitated crystals have started to form some feather like crystals… which matches harmaline description in this paper

https://www.researchgate.net/publication/308363179_A_Harm-Reduction_Approach_To_The_Isolation_Of_Harmine_And_Its_Hydrogenated_Derivatives_From_Peganum_Harmala_Seed_In_Low-Tech_Settings

So ethanol can partition harmalas however may require multiple attempts or something similar to the 4 attempts in that paper.

I’ll try to recystalize the off white/yellow Freebase harmine that didn’t precipitate initially and only after hcl precipitation attempt.

 

[modern]

So both the pretty crystals and the greenish needles are indeed Harmine despite the different visuals of the crystallization and behavior.

The greenish needles first precipitate still had an off-white and a shine. At 7.5ph and the other crystals were just white. However under 365nm light they had a slight yellow-green glow to the powder.

After adding another drop of lye the ph is around 8-8.5ph I think and both produced quite a bit of white much fluffier precipitate In both examples. This however had a slightly orange tone to the powder unlike the first precipitate.

I added more lye to overshoot ph and zero extra precipitate formed. So no harmaline seems to have co precipitated in the ethanol.

I added a small amount of each 4 precipitate in a test tube with vinegar and they all had a blue tone however the second precipitate had a very slightly different blue hue but basically the same.

I’ll try recrystalizing to see if it any differences appear. Happy with results I wanna reattempt this with larger amount of harmalas in the future. Looking forward to trying to get pretty harmaline crystals like the paper.

 

[modern]

The cloudy precipitate from the second ph increase of around 8-8.5ph