The Vespiary

The Hive => Newbee Forum => Topic started by: periannath on March 15, 2003, 08:48:00 PM

Title: Alkylation of amines
Post by: periannath on March 15, 2003, 08:48:00 PM

(I was going to post this to the tryptamine forum but since this could be applicable to any amine I decided to post here.)
Say I had just reduced melatonin to 5-MeO-NET with LiAlH₄ or whatever and reacted it with an excess of methyl iodide to form the quaternary ammonium salt 5-Methoxy dimethylethyltrypammonium iodide. I would get a mixture of 5-MeO-DMT and 5-MeO-MET when I dequat. Correct? :)

Title: Is there anybody out there.
Post by: periannath on March 16, 2003, 05:53:00 PM

All I need is a simple yes or no. If no I would appreciate a reason.

Title: You will likely get almost exclusively ...
Post by: Rhodium on March 17, 2003, 04:02:00 PM

You will likely get almost exclusively 5-MeO-MET, as methyl groups are removed preferentially in most dequaternization reactions.

Title: Thanks
Post by: periannath on March 17, 2003, 04:35:00 PM

Thanks! That was the answer I was hoping for. However I now realize It might be easier methylated with formaldehyde. :)

Title: Tryptamine methylation
Post by: Rhodium on March 18, 2003, 03:33:00 PM

If you UTFSE you will see that not many formaldehyde methylations are tryptamine-friendly (NaBH3CN being an exception).