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Harmaline 'slightly soluble in basic water'? Options
 
Elrik
#1 Posted : 9/3/2020 6:39:19 AM

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Any time I base mixed harmalas the filtered motherliquor is a strong vibrant yellow from dissolved harmaline. I've often read harmaline is 'slightly soluble in basic water' but has this ever been quantified at all? I've seen 'slightly soluble' refer to 1% solubility with some authors.
As a casual proof of concept test I took an aliquot of such motherliquor, added an equal volume of 91% isopropanol and saturated the mix with salt. Most of the yellow migrated to the alcohol layer in room light and most of the neon green migrated to the alcohol layer under blacklight.
Has any effort been put to quantifying the solubility of harmaline base in pH ~9 ammonia water or seeing how much can be reclaimed without extreme measures?
I'm wondering if I could distill off 3/4 of the water, do two alcohol pulls and some follow-up, and manage to get an extra half gram of mostly harmaline from this liquid.
I have 2 kilos of harmala seed so I'm not desperate for yield but I recycle all my solvents so all I'd waste is salt and time Laughing
 

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doubledog
#2 Posted : 9/3/2020 9:40:02 AM

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Ime, pH 9 is too low to precipitate what is left in this yellow solution. If it is still strongly yellow, you could obtain a lot of alks by basing it with some stronger base.
 
Jagube
#3 Posted : 9/3/2020 12:07:57 PM

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Yes, at pH 9 a lot of the harmaline is in salt form.

I don't know harmaline's solubility, but here is something that speaks to its insolubility:
When extracting rue seeds (I do 400 g at a time), I base the combined boils without reducing them. This 400 g seeds worth ends up in 10 liters of basic water.

This still yields ~6% post-manske, with roughly a 45:55 harmine:harmaline ratio, so it doesn't look like a lot of harmaline stayed in solution in the initial basing.
 
Elrik
#4 Posted : 9/3/2020 5:32:31 PM

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Good catch Laughing Okay, forget I said ~9, a 'firm 9' is where I know I'm done when testing with my low grade pH papers. I should never report numbers from these crude papers.
I tested the filtered motherliquor with my actual pH meter and its 9,65.
I took a 5ml portion and added a generous quantity of NaOH (aq) and the yellow color instantly cleared and after two minutes no haze or precipitate formed. It acted as though, yes, some or all of the harmaline was ionized as you say [probably half, since that's nearly its pKa], but when based it was still within the soluble range.
Harmaline glows so intensely I'm not sure just how much is needed to make an intense glow under UV. After working with this stuff it looks like a rave vomited on my hands and arms, I've even painted designs on myself with the waste Laughing
[LSD synthesis would be wild for me if I did it like I do harmalas]
Jagube wrote:
here is something that speaks to its insolubility:
When extracting rue seeds (I do 400 g at a time), I base the combined boils without reducing them. This 400 g seeds worth in 10 liters of water.
Man, some time when I'm feeling playful I need to compare your method to mine. You had me at no reduction.
 
Elrik
#5 Posted : 9/6/2020 7:00:34 PM

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Well I proceeded to experiment with this waste and was unable to recover anything of use, even after notable concentration. So I feel better about dumping it, now.
To my surprise I also isolated an untestable volume of volatile oil from my 4X mansked harmalas. It seems volatile plant oils may 'stick' to harmala•HCl.
Details:
I'm really starting to think that the red-black solids often encountered in work with rue alkaloids are an oxidation product of the alkaloids rather than residual plant gunk.
I'm looking forward to trying Jagubes method now, as a bonus I'll finally get to play with the accessory alkaloids without much extra effort at all.
I wonder if I'll find a practical use for vasicine. Smile
 
 
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