https://www.thevespiary.org/rhodium/Rhodium/chemistry/mexamine.txt (https://www.thevespiary.org/rhodium/Rhodium/chemistry/mexamine.txt)
"I would kiss the ground someone walks on if they can find a use for melatonin.." -Bwiti
Over here next to me, it's a spot where Shulgin stepped.
Melatonin > 5-Meo-DIPT
-Zen
Ref: Tihkal
"To a solution of 3.0 g 5-methoxytryptamine (see under melatonin for its preparation) in 20 mL sulfolane (tetramethylenesulfone) there was added 8.2 g diisopropylethyl amine and 10.7 g 2-iodopropane, and the two-phase mixture was heated on the steam bath with frequent shaking. After 3 h, the mixture was brought back to room temperature and stirred vigorously for an additional 16 h. After the removal of all volatiles under vacuum, the residue (30 g) was diluted with 100 mL H2O, which gave a clear solution. The addition of 10 mL 5% aqueous NaOH produced a cloudy suspension that was extracted with 3x40 mL hexane. These pooled extracts were stripped of solvent to yield 1.0 g of an almost colorless oil that was distilled at the KugelRohr. A small cut at 100 °C (at 0.01 mm / Hg) proved to be largely residual sulfolane (about 0.01 g) and the bulk of the product distilled at 140-150 °C to give a viscous white oil, 0.80 g. This was dissolved in 3.5 mL IPA and neutralized with 15 drops of concentrated HCl. The addition of five drops of anhydrous Et2O instigated crystallization, and the product was removed by filtration, washed with 4:1 IPA / Et2O mixture, and air-dried. There was thus obtained 0.85 g of a fine white crystalline product, 5-methoxy-N,N-diisopropyltryptamine hydrochloride (5-MeO-DIPT), with a mp 181-182 °C (17%). IR (in cm-1): 731, 809, 826, 931, 1035, 1064, with an NH at 3165. MS (in m/z): C7H16N+ 114 (100%); C4H10N+ 72 (31%); methoxyindolemethylene+ 160 (12%); parent ion 274 (<1%). There was no detectable 5-MeO-NIPT by GC (<1%)."
http://www.erowid.org/library/books_online/tihkal/tihkal37.shtml (http://www.erowid.org/library/books_online/tihkal/tihkal37.shtml)