I read shulgin`s book TIHKAL and notice when he alkylates typtamine with ethyl bromide.
And eliminates alkylbromides from the quarternary ammonium halides with diazabicyclooctanes.
Why doesn`t the indole nitrogen get alkylated???
Call me stupid about tryptamine chemistry I don`t care...

Because the indole nitrogen is not a normal amine. The nitrogen lone electron pair is donated to the aromatic ring system. Protonate or alkylate it and you destroy aromaticity - energetically very unfavorable....

That answers my question thanks for the insight.