HI guys! I am new here and have some questions about a/b extraction. I am pretty new to theory, so I wrote out my logic to help myself understand what I am trying to convey, and hopefully it helps the reader get an idea for my logic and the possible flaws it contains.


I am thinking about an approach to Anadenanthera colubrina extraction of bufotenin and dmt. I am by no stretch of the imagination a chemist, so bear with me if this is off center thinking. I have read many of the posts of A/B extraction and have a question about sodium bicarbonate use, as I have not seen much sodium bicarbonate being employed in the extractions.

I have considered that acetic acid, HCl and citric acid are all appropriate for the generation of amine salt for pushing the alkaloid in the the aqueous layer. Many people report good experiences, and the pKa is in agreement. Then for returning the bufotenin back to freebase I considered sodium bicarbonate, as it is traditionally used in extractions were the salt formation of a phenol is not desired. I know the alcohol is not a true phenol and that there are additional ressonace structures ,which although unstable and unlikely to be favored, may contribute to lowering the pka of the alcohol. I can see the advantages of using a weaker base like calcium carbonate in light of this in the extraction to avoid the formation of a salt at the alcohol, but is it completely necessary? I know baking soda is easy to find, but not sure on where carbonate is available besides the internet, so this is why I ask. Has anyone had good crystalization with just using sodium bicarbonate? Does anyone have comparative experience?
Also, I see alot of hydroxide salt use on this forum for bufotenin extraction, I must be missing something because it seems the hydroxide would just deprotonate the alcohol and form a salt of bufotenin and work against the extraction; however, it seems the reported sucess speaks otherwise so i must be out of the loop somewhere.
Finally, has anyone have report on defatting with xylene, it seems to be the best possible solvent. Acetone and diethyl ether seem to be popular on this site, and sound like a great idea considering health and volatility, but xylene looks so attractive even with all of its carcinogenic goodness.