Sorry for my somewhat belated joining of the party.
First, a few words to Loveall.
Regarding the cleaving of the methoxy group from harmala alkaloids, I would like to reference the horse's mouth, R.H.F. Manske himself.
From page 50 of "The Alkaloids" @ google books :
From the above description, it seems reasonable to conclude that attemting to convert harmine or harmaline into harmol or harmalol is certainly not a kitchen-safe procedure. Refluxing fuming hydriochloric acid @140C would not be the worst part, the methyl chloride would. Methyl chloride is a dangerous carcinogen, and furthermore has considerable acute toxicity.
Methylating the phenolic oxygen of harmol and harmalol is not as easy as simply adding a methylating agent (almost all of which are dangerous carcionogens, btw). Apart from the practical aspects of actually getting the methylating agent to react at all, how will you prevent it from methylating either of the two nitrogens on the molecule instead?
Oh, and Loveall, don't attempt to methylate mercuric chloride with vitamin B12, not in your kitchen, not anywhere. At least not before you have read about the fate of Karen Wetterhahn, a highly experienced organometallic chemist, how accidentally spilled a few drops of dimethylmercury onto her glove.
Regarding 69ron, he was certainly a trove of useful knowledge on various matters relating to extractions of alkaloids. Yet he also had a quite a few run ins with some of the more esteemed chemists on this forum, who occasionally took issue with 69ron making bold claims without providing proper proofs or references to back up his assumptions.
Now, onto the meat of the original topic.
My rough guess is that the "manske" salting out of reasonably pure harmala hydrochlorides has a yield of 95%, meaning that 5% will be left in solution. From the filtrate, these 5% can be freebased, collected and acidified to be re-salted in an appropriately smaller volume in order to collect most of the lost yield.
Having said that, I want to re-emphasize the "reasonably pure" part in the above paragraph. Meaning, that on performing the initial "maske" salting, the solution is not likely to contain only harmala alkaloids, but many other substances, both in solution and in suspension. To assume that the only other substance present would be the quinazoline vasica alkaloids, is only an assumption, not supported by any analytical evidence. Likewise, there is not factual basis for assuming that the non-precipitated harmalas from salting are be harmol and harmalol.
I suspect that many other plant derived substances will still be present, even after a few acid-base cycles. The slimyness of the observed precipitates suggests the presence of proteins. That is, admittedly, an assumption. My personal observation is that basing the filtrate from a salting of refined harmala alkaloids begets a far less slimy precipitate than that which is obtained from basing the filtrate of the first saltings of a rue extract.
First, a few words to Loveall.
Regarding the cleaving of the methoxy group from harmala alkaloids, I would like to reference the horse's mouth, R.H.F. Manske himself.
From page 50 of "The Alkaloids" @ google books :
From the above description, it seems reasonable to conclude that attemting to convert harmine or harmaline into harmol or harmalol is certainly not a kitchen-safe procedure. Refluxing fuming hydriochloric acid @140C would not be the worst part, the methyl chloride would. Methyl chloride is a dangerous carcinogen, and furthermore has considerable acute toxicity.
Methylating the phenolic oxygen of harmol and harmalol is not as easy as simply adding a methylating agent (almost all of which are dangerous carcionogens, btw). Apart from the practical aspects of actually getting the methylating agent to react at all, how will you prevent it from methylating either of the two nitrogens on the molecule instead?
Oh, and Loveall, don't attempt to methylate mercuric chloride with vitamin B12, not in your kitchen, not anywhere. At least not before you have read about the fate of Karen Wetterhahn, a highly experienced organometallic chemist, how accidentally spilled a few drops of dimethylmercury onto her glove.
Regarding 69ron, he was certainly a trove of useful knowledge on various matters relating to extractions of alkaloids. Yet he also had a quite a few run ins with some of the more esteemed chemists on this forum, who occasionally took issue with 69ron making bold claims without providing proper proofs or references to back up his assumptions.
Now, onto the meat of the original topic.
My rough guess is that the "manske" salting out of reasonably pure harmala hydrochlorides has a yield of 95%, meaning that 5% will be left in solution. From the filtrate, these 5% can be freebased, collected and acidified to be re-salted in an appropriately smaller volume in order to collect most of the lost yield.
Having said that, I want to re-emphasize the "reasonably pure" part in the above paragraph. Meaning, that on performing the initial "maske" salting, the solution is not likely to contain only harmala alkaloids, but many other substances, both in solution and in suspension. To assume that the only other substance present would be the quinazoline vasica alkaloids, is only an assumption, not supported by any analytical evidence. Likewise, there is not factual basis for assuming that the non-precipitated harmalas from salting are be harmol and harmalol.
I suspect that many other plant derived substances will still be present, even after a few acid-base cycles. The slimyness of the observed precipitates suggests the presence of proteins. That is, admittedly, an assumption. My personal observation is that basing the filtrate from a salting of refined harmala alkaloids begets a far less slimy precipitate than that which is obtained from basing the filtrate of the first saltings of a rue extract.
) and harmalas alkaloids are not very soluble in alcohol.. i think this idea might work better in a DMT extraction using ISO
