Alkylation of amines

[periannath]

(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?

[periannath]

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

[Rhodium]

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

[periannath]

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

[Rhodium]

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