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Extra resources for TIHKAL. Tryptamines I Have Known And Loved [part 2 only]
And there you have a new, firmly established fact of science to add to the understanding of the universe. A case in point. What happens when you put a methyl group on the two-position of the indole ring of a tryptamine. In the three examples, examples of the best studied tryptamines that were not active orally, they all became orally active. DMT, DET and 5-MeO-DMT, the three major parenterally-only active psychedelics, all blossomed into orally active compounds with the addition of a simple methyl group to that indole 2-position.
After standing overnight, the excess hydride was destroyed by the cautious addition of 500 mL wet Et2O, followed with 70 mL H2O, 100 mL THF, and finally 20 mL 50% NaOH. 5 L Et2O, the combined filtrate and washings dried over anhydrous K2CO3, and the solvent removed under vacuum. The residue, 78 g, was dissolved in 100 mL MeOH, treated with 12 mL acetic acid, stripped of volatiles under vacuum, redissolved in a mixture of 250 mL ethyl acetate and 30 mL MeOH, concentrated to a volume of about 100 mL, and again treated with 2 mL acetic acid.
11. a-ET ALPHA-ETHYLTRYPTAMINE; INDOLE, 3-(2-AMINOBUTYL); TRYPTAMINE, ALPHAETHYL; 3-(2-AMINOBUTYL)INDOLE; MONASE SYNTHESIS : To a 50 °C warmed mixture of 60 mL glacial acetic acid and 18 mL acetic anhydride, there was added 66 g crystalline ammonium acetate and stirring continued until solution was complete (20 min). To this there was added a solution of 87 g indole 3-carboxaldehyde and 300 mL nitropropane in 360 mL acetic acid. The mixture was held at reflux temperature for 3 h, cooled, and diluted with 360 mL H2O.
TIHKAL. Tryptamines I Have Known And Loved [part 2 only] by Shulgin