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Author: Subject: demethylation of tryptammonium iodide
mackolol
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[*] posted on 12-9-2018 at 06:18
demethylation of tryptammonium iodide


As i'm going through Shulgin's book TIHKAL for last days i came across DMT synthesis. It is synthesis that uses triethyl tryptammonium iodide. As i see it's quite difficult, and i'm wondering why couldn't one just add NaOH and make freebase from this quaternary ammonium salt instead of hard demethylation. And if i'm correct methyl group is that one hard to remove as in case of DIPT synthesis he just adds isopropyl iodide to tryptamine and makes freebase from it with lye. So why can't it be made with methyl iodide as well?
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Loptr
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[*] posted on 12-9-2018 at 06:25


Likely due to steric hinderence that moderates overalkylation to a quaternary amine. Methyl iodide would be a lot more mobile for the same reason..lack of steric hinderence.

EDIT: I meant that the addition of isopropyl iodide to the nitrogen is probably limited to dialkylation due to steric hindrance, so the NaOH isn't dealkylating anything because it was never a tertiary amine.

[Edited on 12-9-2018 by Loptr]




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mackolol
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[*] posted on 12-9-2018 at 10:20


ok thanks very much.
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