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separation or conversion of harmine from harmaline

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T

Tribal

Rising Star
I just read the "Harmaloids by themselves?" thread. Now it seems like a worthwhile endeavor to try harmine alone without harmaline, and visa versa. However, I'm guessing that a lot of SWIY's are probably sitting at home with some rue extract which contains both, and in differing ratios. So, it definitely seems like it might be a nice thing to know how one might be able to separate harmine and harmaline from a rue extraction, and I can't seem to find a topic that covers this.

If separation isn't an easy task, then is it possible to convert harmaline into harmine to at least get one of the two isolated? I think I read on another thread that harmaline can break down into harmine when heated, but can't find it.

Anyone know of a separation or conversion tek?
 
gotta go now so cant write much but yes, its easy to separate them.. They have different pka's which means that they become freebase at different pHs.. I forgot which is which, but if you slowly add a base to an acid solution containing the harmalas, then first one of them will precipitate.. Then one separates/decants/filters/whatever, and continue adding the base so that the other one precipitates. Quite simple :)
 
I did a little more research on this. The only tek I could really find was on Erowid, and it didn't make it sound very easy. It was based on conversion of HCl salts to freebase using ammonia and required a microscope to determine when the harmaline crystals start to crash after the harmine. In my opinion the acetate salts converted to freebase by sodium carbonate solution seems like a much better route, but I'm not sure this method would work that way.
 
Thank you Phlux! I knew it would be here somewhere, but difficult to locate sometimes

Ok, so:
the pka of harmine is about 7.07 or 7.45
the pka of harmaline is 9.55
pka is the pH at which a substance exists half in its ionized form and half in its freebase form

With the harmaloids in salt form use sodium carbonate to basify the solution to about 8.5 or a little below. The harmine will precipitate out. Allow it to settle and decant the liquid. The solids should be mostly freebase harmine.

Next raise the pH of the previously decanted liquid above 9.55 and more solids will precipitate out, which will be mostly freebase harmaline.

Now THAT does sound easy.
 
If swim wanted a really nice pure separation how would it be best for him to go about doing so - he has a very accurate pH meter now.
 
well just slowly add the sodium carbonate/ammonia, wait a little bit for it to mix and the readings to be accurate... and then just stop adding when desired pH is reached. Then decant/filter, but save the liquid.. Then after first alkaloids are out, keep adding the base for the second one to precipitate, and then decant/filter again
 
hahaha - yeah i know the proceedure - we just discussed it but i was thinking that if i push the ph up to 8.5 i will have harmaline contamination in my harmine - what im looking to do is a very accurate separation and was wondering the specific ph to do it at - like what is the ph that only harmine will drop out at without any traces of harmaline (7.45 ?), can it be done in 1 go or does this proceedure need to be repeated to clean up etc.
swim would really like to have the 2 separated 100% so he can play with the conversion teks.
 
okay so swim started on this - gona make a full foto tek afterwards
the solution is at ph 7.14 atm - gonna see if anything precips - if not the ph will be raised to 7.54, ...
 
ok so the bowl is nice and full of needle shaped xtals - precipped overnight at pH 7.14
how the hell does one filter this without breaking up the nice structure - even breaking the xtal structure how is it best to proceed - swim hates filters and only has coffee filters.
some xtals are floating, some are on the sides and some have sunk.
 
everything was filtered - yeilded 156mg needle like orange brown xtals.
ph was pushed to 7.45 and loads more has precipitated - perhaps the same amount as the first batch.
this will be left overnight again and xtals collected in the morning.
the xtals are needle like but slightly joined to form flat surfaces(floating) - not disks tho - what does harmaline look like as swim wants pure harmine and needs to know how to keep an eye out for it - harmaline will be precipped after all the harmine is out.
the starting amount for the mixture was 500mg off white harmaline/harmine from rue.
 
Phlux- said:
everything was filtered - yeilded 156mg needle like orange brown xtals.
ph was pushed to 7.45 and loads more has precipitated - perhaps the same amount as the first batch.
this will be left overnight again and xtals collected in the morning.
the xtals are needle like but slightly joined to form flat surfaces(floating) - not disks tho - what does harmaline look like as swim wants pure harmine and needs to know how to keep an eye out for it - harmaline will be precipped after all the harmine is out.
the starting amount for the mixture was 500mg off white harmaline/harmine from rue.
Click to expand...
Phlux-,

See this thread; SWIM has calculated that the pH at which someone gets most of the harmine with the least possible harmaline contamination is 8.75. SWIM has also included a graph showing roughly what harmine/harmaline quantities one should expect to precipitate at different pH values.
 
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