Sister has received some requests for a tek to separate NMT and DMT.
Sister should also mention that her experiments using aspirin where inspired by a thread over at Science madness (Sciencemadness Discussion Board - question an N-acetylation of aniline, using aspirin - Powered by XMB 1.9.11 (Debug Mode)) where Jor was acetylating aniline with asprin. However, this was some time ago and it received little attention at the time. There are also many references in literature for the in-vivo acetylation of prostaglandin synthase with acetylsalicylic acid. This is also very handy technique to remove 1° and 2° amines from mixtures of 3° amines. (In other words a way to remove NMT from a mixture of NMT and DMT)
This method is simple, clean and fast.
Dissolve a 1.2 molar XS of aspirin1 (relative to tryptamine) in the minimum amount of boiling EtOH (other alcohols like IPA or MeOH will also work, but solubilities will vary). Some of the binders will not go into solution, but it doesn’t matter, they will not affect the rxn (you can decant the solution from the undissolved binders if it bothers you). Dissolve your tryptamines in the minimum amount of boiling alcohol. Remove from heat and let both stand long enough to cool by 1-2 degrees, then combine the two mixtures and heat to boiling again for 1-2 minutes. Remove from heat and allow to cool to room temp. Acidify the mixture with 2X volume of acidic H2O and wash 3X with a suitable non polar solvent (DCM, Toluene, Xylene, Ether, Ethyl Acetate but NOT Naptha). This removes the acetylated NMT from the mixture. You can also back extract the NP washes with a little acidic H2O if you want to be meticulous. Discard the NP washs or distill to recycle the solvent. Take the acidic post reaction mixture (and acidic back extraction) and slowly basify with 25% NaOH. Extract it with the non polar solvent of your choice (Naptha can be used here) and evaporate/distill your solvent or freeze precipitate as usual to yield only the 3° amines (nn-dmt).
That’s it, you’re done. 8)
1. acetylsalicylic acid 180 g/mol, tryptamine 160 g/mol
2. You can follow this RXN on TLC. Using a 3/1 EtAcO/MeOH, tryptamine will have an rf of 0.1 – 0.2, NMT 0.3, while your n-acetyl tryptamine will have an rf of 0.6 - 0.7.
Sister should also mention that her experiments using aspirin where inspired by a thread over at Science madness (Sciencemadness Discussion Board - question an N-acetylation of aniline, using aspirin - Powered by XMB 1.9.11 (Debug Mode)) where Jor was acetylating aniline with asprin. However, this was some time ago and it received little attention at the time. There are also many references in literature for the in-vivo acetylation of prostaglandin synthase with acetylsalicylic acid. This is also very handy technique to remove 1° and 2° amines from mixtures of 3° amines. (In other words a way to remove NMT from a mixture of NMT and DMT)
This method is simple, clean and fast.
Dissolve a 1.2 molar XS of aspirin1 (relative to tryptamine) in the minimum amount of boiling EtOH (other alcohols like IPA or MeOH will also work, but solubilities will vary). Some of the binders will not go into solution, but it doesn’t matter, they will not affect the rxn (you can decant the solution from the undissolved binders if it bothers you). Dissolve your tryptamines in the minimum amount of boiling alcohol. Remove from heat and let both stand long enough to cool by 1-2 degrees, then combine the two mixtures and heat to boiling again for 1-2 minutes. Remove from heat and allow to cool to room temp. Acidify the mixture with 2X volume of acidic H2O and wash 3X with a suitable non polar solvent (DCM, Toluene, Xylene, Ether, Ethyl Acetate but NOT Naptha). This removes the acetylated NMT from the mixture. You can also back extract the NP washes with a little acidic H2O if you want to be meticulous. Discard the NP washs or distill to recycle the solvent. Take the acidic post reaction mixture (and acidic back extraction) and slowly basify with 25% NaOH. Extract it with the non polar solvent of your choice (Naptha can be used here) and evaporate/distill your solvent or freeze precipitate as usual to yield only the 3° amines (nn-dmt).
That’s it, you’re done. 8)
1. acetylsalicylic acid 180 g/mol, tryptamine 160 g/mol
2. You can follow this RXN on TLC. Using a 3/1 EtAcO/MeOH, tryptamine will have an rf of 0.1 – 0.2, NMT 0.3, while your n-acetyl tryptamine will have an rf of 0.6 - 0.7.
