.

Nice paper Benzyme. Thanks. Sister was surprised to read that ChCl3 is acidic. She has used it to wash acidic aqueous solutions containing alkaloids and now wonders if some of the yield has disappeared with the washs? Sounds like back extraction is in order ...

ooo.. you used a haloform to wash an acidic aqueous phase? they have dipole moments.
i'd use an aliphatic

Yes Dr Sister, defatting with chloroforom can make you lose yield, for example DMT acetate is somewhat soluble in chloroform.

she's talking about alks in a protonated solution, they're not salts. dmt acetate doesn't exist until the aqueous phase containing acetic acid is evaporated.
water is somewhat miscible in chloroform (0.815%). any potential loss could be reduced by making the solution strongly acidic (pH 1), or using a solvent with no dipole.
naphtha or heptane would be preferable for a defat.

Excuse my lack of exactitude but point still remains. Banerjee & Ghosal 1969 states that a chloroform layer with alkaloids from Desmodium gangeticum was extracted with 2N aqueous acetic acid solution. DMT and DMT N-Oxide were in both phases, (amounts only given for n-oxide, 210mg was in acqueous layer, 120mg in chloroform).

Conclusion from my non-chemist perspective: If you defat with chloroform, evap it and see if you can retrieve alkaloids from it.

that may be implemented as part of the partitioning scheme; the other part would include basification, followed by a two-step binary solvent extraction using toluene and ethyl acetate. the goal is to separate the alkaloids based on their relative polarities.
5-meO would be very easy to separate with these solvents

NIce been looking for this! Looking at the paper, I cant possibly understand it. Would love if somebody could boil down the process in laymens terms, and what one would have to do in each step. If one had a mix of dmt and 5 meo dmt and wanted to seperate it.



I might not understand the whole process, but "toluene and ethyl acetate."
Lets say one had a mix of dmt, 5 meo.

Should one make a mix with those solvents, then drop the dmt, 5 meo in there so they seperate automaticly? then pull each layer and then evaporate? In that case, how would one know which layer contain the dmt, 5 meo. Hehe I might of missed something huge here. Would love some input

^ mm it's not going to work like that.


Chloroform is very slightly acidic because it is pretty polar (the chlorines are pulling the electrons away from the carbon, and in sum, the hydrogen), and that proton on the top there is on there tight, but there is enough dipole there, it is possible for it to lose hold of its electron, and fall off.



But if you just mixed toluene and ethyl acetate together, there is no easy separation. The solvents are going to solvate themselves, as well as the alkaloids. Its all going to be a big mix of molecules

--
edit, whoa that's a big molecule

whoa that's a big molecule.

sync*