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Extraction with Acetone

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xdragon said:
With acetone being bulkier than formaldehyde, imine formation and cyclisation rate will definitely be slower.
Acetone and DMT will not form N-isopropylidene-DMT, and Pictet-Spengler cyclization will not take place. DMT is a tertiary amine, it lacks the N-H bond that would allow the ketimine to form through a carbinolamine intermediate.
 
Hailstorm said:
xdragon said:
With acetone being bulkier than formaldehyde, imine formation and cyclisation rate will definitely be slower.
Acetone and DMT will not form N-isopropylidene-DMT, and Pictet-Spengler cyclization will not take place. DMT is a tertiary amine, it lacks the N-H bond that would allow the ketimine to form through a carbinolamine intermediate.
Yes, although both NMT and tryptamine itself will form N-isopropylidene derivatives.

xdragon - inductive effects from the two methyl groups will also make the carbocation-equivalent centre less electrophilic so it's not just steric considerations that will be affecting the reaction rate.
 
Sorry to dig up an old thread.. this is the only info I can find on freeze precip with acetone.

I am attempting to crystalize an Acacia floribunda extract.. this species is notoriously difficult to obtain a solid extract from. It is usually an amber/yellow oil/toffee texture.

I have been attempting to precipitate DMT from acetone .. at first it looked very promising. I dissolved my alkaloids in a small jar. The acetone took on a deep red colour.

After about half an hour in the freezer, cream coloured precipitate was noticed floating in the solution. I filtered the solids onto a coffee filter and dried them. They ended up a “putty” like texture and were a dark brown when scraped up.

The precipitate is far less sticky than the usual difficult to handle extract but it seems the majority of the DMT remained dissolved.

I’m not at all bothered if the extract crystallizes - my hope is to at least get it to a point where it can be dried and scraped up. It’s difficult to store otherwise. Whatever the really sticky stuff is, it’s still highly soluble in cold acetone which is encouraging.

I then evaporated the acetone in a separate dish, which yielded what seemed to be the bulk of the extract still.. again, an amber oily consistency. Both the precipitate and the evaporated acetone are highly active.

@benzyme .. is there a certain level of saturation required with acetone to drop all of the alkaloids out when freeze precipitating?

This seems like a potentially good way to tidy up Acacia floribunda extract. But the precipitates were a fraction of the total extract.

Any advice would be greatly appreciated.

Below a shot of the jar fresh out of the freezer.
 

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Hi,
You can try calculate with already extracted DMT the saturation at RT for example.

On the other hand, you can salt the dmt out with an acid with no effort. Really good foor storage :)
 
I don’t have any fumaric acid.. do you think a little citric acid would work ok? I would then probably do a mini a/b on the precipitate .

Thanks for the quick response!
 
Perhaps you could add a bit of water as is outlined here? Maybe that could lower solubility enough while still not freezing the solution at low temps.
 
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