periannath (Stranger)
03-15-03 20:48
No 417492
       Alkylation of amines  Bookmark   

(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?smile
Wherever you go, there you are.
-Buckaroo Banzai 		 
 
 
 
    periannath
(Stranger)
03-16-03 17:53
No 417812
       Is there anybody out there.  Bookmark   

All I need is a simple yes or no. If no I would appreciate a reason.
Wherever you go, there you are.
-Buckaroo Banzai 		 
 
 
 
    Rhodium
(Chief Bee)
03-17-03 16:02
No 418202
       You will likely get almost exclusively ...  Bookmark   

You will likely get almost exclusively 5-MeO-MET, as methyl groups are removed preferentially in most dequaternization reactions. 		 
 
 
 
    periannath
(Stranger)
03-17-03 16:35
No 418220
       Thanks  Bookmark   

Thanks! That was the answer I was hoping for. However I now realize It might be easier methylated with formaldehyde.smile
Wherever you go, there you are.
-Buckaroo Banzai 		 
 
 
 
    Rhodium
(Chief Bee)
03-18-03 15:33
No 418809
       Tryptamine methylation  Bookmark   

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