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converting inactive harmala red crystals back to active harmine/harmaline

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lorax

lorax

Rising Star
a friend had extracted from 100g peganum harmala and has ended up crystallizing them out of 96.6% ethanol. This was recommended in some tek. Then someone on this forum told him that the resulting red crystals were called harmala red and are inactive.

is there any way of converting them back or is my friend now stuck with very nice red dye for persian carpets?
 
Very little is known about harmala red.

The active harmala alkaloids are sometimes red just from impurities in the seeds. It doesn’t necessarily mean they’ve all converted to the inactive harmala red.

They are probably not all converted to harmala red. You should be able to test this easily. Harmala red is supposed to be insoluble in water but highly soluble in alcohol. If you can dissolve it all in a little tiny bit of water, it's not converted, I believe.

I’ve never seen a way to convert harmala red back into harmaline.

Harmala red looks sort of gelly-like, like little pieces of red gelatin. It can sometimes coat the harmaline and harmine, making them look red.

Here's some harmala red forming from harmaline after evaporating from alcohol. This was shot with a microscope at about 80x.



Harmala Red Forming from Harmaline HCl
resource.ashx


It doesn't look appetizing does it? Kind of slimy looking. The yellowish needles are the harmaline hydrochloride, the red stuff is harmala red. These were once pure yellow needles until dissolved in alcohol and evaporated. This was the result.
 

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the stuff which my friend has looks like red oily crystals.. they're pretty translucent red tho.. my guess is that they are red because my friend used himalaya rock salt for the procedure. this salt is pinkish in color. he didn't find any other rock salt so he used that.
 
do you think that there might be a way of removing the red color coming form the salt? do you think this might be color coming from minerals and other useful stuff contained in the salt? i wouldn't mind any minerals or other good stuff in my alkaloids..
 
The seeds of Syrian Rue contain a red dye'
My question is this'

If the Harmine was dissolved in alcohol and the alcohol turned red'
Where is it said that these alks are inactive'
The dye in the seeds is inactive' but of where does it say that Harmine dissolved in alcohol turns it red and makes the Harmine inactive'

Anyone got links'

Bliss

Nobuoni +

If you read all the chemistry done on Harmine' it never mentions the methanol/ethanol turning red' this is of when pure Harmine is put into methanol/ethanol solution'

If you extract Harmine etc from Rue seeds' it is going to be red' cos they contain lots of the dye' until you salt out the Harmine a few times'
Then you got the problem of the Harmine containing sodium chloride' of which can no be taken with a moai'
Sodium chloride is practicaly insoluble in alcohols' so it would seem a simple act to dissolve the lot in alcohol' the sodium chloride falls to the bottom of the solution' the Harmine dissolves in the alcohol'
tryed this with salted alks from Rue' the alcohol turned instantly red'
Upon evaporation the product was completely dry' red/brown/yellow/sparkly' and made the tongue go numb'

Anyone tested this end product' extracted from Sirian Rue' that turned the alcohol red ???
 
There are several books out there that talk about harmala red. It forms from harmaline in alcohol but not harmine in alcohol.

Look at Hand-book of chemistry By Leopold Gmelin, Henry Watts, page 120. It's stated that harmala-red is a “product of oxidation of harmaline".

Dictionary of Arts, Manufactures and Mines By Andrew Ure, Robert Hunt, page 576, it says that harmala red is "obtained by digesting the seed in alcohol for some days".

Elements of Chemistry: Theoretical and Practical By William Allen Miller on page 546 says that with harmaline "oxidizing agents transform it into a red colouring matter which combined with acid, forming salts which constitute the bases of the harmala red of commerce."

Year-book of Pharmacy By Pharmaceutical Society of Great Britain, page 601, it says that the "most interesting fact concerning these seeds which immediately claims attention, is the magnificent green fluorescence which they impart to alcohol of about 75 percent. This optical power is partly due to a substance called harmin, and partly, it would appear, to the formation of a peculiar colouring matter named harmala-red, which has not yet been fully examined, but which does not pre-exist in the fresh seeds."

SWIM tested it and indeed harmala red forms from harmaline when left in alcohol for some time and he has pictures above to prove it. SWIM never tested it for activity though.
 
All the chem techs for recrystalisation use 1:1 Methanol/Benzene' or absolute Methanol'

This >>> that turned Harmaline red'
was done in ethanol ?

Bliss

Nobuoni +

The HCL's from Rue where dropped into a solution of Methylated spirits' the solution turned instantly red' (summise that this was down to the Methyl violet that Methylated spirits has in it'
Upon evaporation the product was completly dry' red/brown/yellow/sparkly'
The product was no tested other than a smidge on the tongue (tongue went numb) becasue it had Methyl Violet in it'
Methyl Violet turns red in acid solutions and yellow in base'

This oxidisaion mentioned would seem to take time'
The solution tested went red instanly'

++++
+++
 
Nobuoni said:
All the chem techs for recrystalisation use 1:1 Methanol/Benzene' or absolute Methanol'

This >>> that turned Harmaline red'
was done in ethanol ?

Bliss

Nobuoni +
Click to expand...

Yes done in ethanol or isopropyl alcohol as harmaline hydrochloride, but NOT done as harmaline freebase. I don't know if it has any effect on freebase harmaline. I never heard of methanol or benzene making harmala red.
 
if it doesnt form harmala red with freebase, then this is easy to take care of, just redissolve harmala salts in a solution, raise pH, let the freebase precipitate, decant/filter and whatever is left redissolve in alcohol to separate harmalas freebase from some of the impurities...

plus the fact that there will be not sodium chloride anyways because once one redissolves the harmala salts in a solution and raises the pH, the sodium chloride will stay dissolved in the water and wont crash out.
 
So freebase with sodium carbonate' filter' then wash with Methanol to extract the base alks' leaving any un-solubles behind'
Ok' shall give this a go'
Still poses the question is this red stuff active'
Thanks bro'

Bliss

Nobuoni +

P.S. Salted out extract' light brown yellow added to 50ml Methanol'
The Methanol went instantly red/brown'
But there are 22 alkaloids in the seeds' soany one could be the reason for the red' or a combo of many'
 
Harmala red is formed when freebase harmalas dissolved in limonene are heated to the boiling point of water. So, this doesn't appear to be something that is exclusive to alcohol.
 
Hope this helps:

SWIM tried to dissolve freebase harmalas into methanol for the purpose of forming big crystals, only to realize freebase harmalas don't dissolve well in methanol (required very large volumes of methanol to dissolve only 2 grams of freebase) and also upon slow evaporation, no crystals were formed, only the same powder was left, with a change in color, but the exact name of the color escapes my memory, SWIM got angry and discarded all that failed shit.
 
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