• Members of the previous forum can retrieve their temporary password here, (login and check your PM).

Harmala recrystallization in alcohols, FB or HCl? Iso or EtOH?

Migrated topic.
Elrik

Elrik

Rising Star
So I was playing with the last of my impure mixed harmalas, trying to get it cleaner. After trying a few other tactics I freebased and I did a recrystallization of the freebased alkaloid in wet isopropyl alcohol before converting back to the hydrochloride. It changed the dirty dark orange sample to a dark yellow sample and left behind red alcohol.
Now that I'm out of impure harmalas I'm wondering, will the hydrochloride itself recrystallize in a reasonable volume of isopropanol? If so what would be a good water content?
I opted for isopropanol because ethanol is routinely contaminated with bitrex. Is there any factor that might make ethanol superior enough to search out a bitrex-free supply for recrystallizations? At least with the freebase, it wouldnt surprise me if more alkaloid stayed dissolved in the ice cold isopropanol.

From a practical point of view I realize there is no strong reason to want super-pure harmalas but it blew my mind recently when I got some white harmine hydrochloride, now I want an easy way to get my alkaloids that clean just for prides sake if nothing else 😉
 
Elrik said:
So I was playing with the last of my impure mixed harmalas, trying to get it cleaner. After trying a few other tactics I freebased and I did a recrystallization of the freebased alkaloid in wet isopropyl alcohol before converting back to the hydrochloride. It changed the dirty dark orange sample to a dark yellow sample and left behind red alcohol.
Now that I'm out of impure harmalas I'm wondering, will the hydrochloride itself recrystallize in a reasonable volume of isopropanol? If so what would be a good water content?
I opted for isopropanol because ethanol is routinely contaminated with bitrex. Is there any factor that might make ethanol superior enough to search out a bitrex-free supply for recrystallizations? At least with the freebase, it wouldnt surprise me if more alkaloid stayed dissolved in the ice cold isopropanol.

From a practical point of view I realize there is no strong reason to want super-pure harmalas but it blew my mind recently when I got some white harmine hydrochloride, now I want an easy way to get my alkaloids that clean just for prides sake if nothing else 😉
Click to expand...

Your better off with A/b cycles as a cleanup step than recrystallizations. Harmalas are soluble in ethanol & isopropanol but only slightly. You might try pure methanol if you are dead set on recrystallization but im sure you are aware methanol is fairly toxic & i am not entirely sure how much more soluble it is in methanol than ethanol or iso.

After the initial extraction & basification further a/b cycles are capable of yeilding white harmalas that seem to be a lot more potent than cruder extracts but i couldnt really offer any insight into what the ceiling on purity via repeated a/b cycles & washing may be.
 
Interesting, in my tests on this dirty material B/A cycles did little to clean it, less than manske cycles. I even tried basing it out very slowly in the presence of ascorbate since ascorbate has its strongest reduction potential in basic solutions.
In all instances I based with excess ammonia. It sounds like I'd need to push the pH up to 13 with lye to get the harmala red removed by basing.

A little is lost in any purification be it basing, recrystallization, or manske.
 
using alcohols should work for recrystallizing the salt. I have considered doing this myself to recrystallize the HCl salt simply because I don't like storing things as freebase. Harmine/harmaline freebase appear to be quite stable though, so I haven't got around to it.

IPA should work just fine, but its always a matter of testing to see what works best. ethanol and methanol respectively will be better at dissolving the salt, but ideally you want it to be very soluble at boiling temperatures but insoluble at freezer temperatures
 
Thanks guys.
I dont know how I missed that 'Harmala Alkaloid Solubilities' thread. There are some useful leads there, but it seems there is no confident answer yet. I'll drop any quantitative observations in there. I can already say I like the look of recrystallizing hydrochlorides better than my freebase attempt. The freebase gave a microcrystalline precipitate from 66% IPOH that was slow to gravity filter, the hydrochloride is giving visible crystals from 91% IPOH.
 
Back
Top Bottom