Imine Contamination of Tryptamine from Tryptophan Decarboxylation using Acetone for Extraction

[PunchPacket]

In many of the amateur chemist procedures that I've read online around tryptophan decarboxylation, acetone is used as the extracting solvent sometimes even used as the catalyst for the decarboxylation itself. Ketones and aldehydes readily form imines with primary amines, in our context "n-isopropylidene-tryptamine," this contamination is accelerated when an acid/base extraction is performed as the addition of any acid catalyzes the amine to imine reaction.

My guess is acetone is used due to how easy it is to obtain, however it's an easy way to containment your end product. Chloroform and DCM can be used but aren't very OTC friendly, there are certainly easier solvents to obtain but I'd need to do some more digging on that.

Would anyone be able to shed some light on substitutes for solvents and if the ketones used during the decarboxylation/extraction are a problem for the purity of the desired end product?

 

[WillD]

Write a full method, and we will try to help

 

[PunchPacket]

Write a full method, and we will try to help

William DampierTook me a while to fix the forum editor. I made the image below as an example and I linked a journal that relates to what I am trying to highlight.

Would the ketones used effect the outcome of the end product by reacting and forming these imine side products?

https://www.dea.gov/sites/default/files/pr/microgram-journals/2011/mj8-1_29-35.pdf

 

[woohoo]

If you on way to dmt through reduction, it should give MIPT, but fraction will be very low.
It's obviously, any ketone react in that way even in small ammounts.

 

[WillD]

I think this is only possible at room temperature and long mixing of the product with acetone. If the mixture in the freezer and after is filtered through a vacuum, such impurities are minimized.

 

[Hailstorm]

OP, just gently microwave tryptophan in carvone and perform an A/B extraction. There's a detailed write-up on DMT Nexus.
Imines undergo hydrolysis in aqueous acid.