TiHKAL #33 2-ME-DET

SYNTHESIS : To an ice-cold and stirred solution of 6.56 g 2-methylindole in 75 mL TBME there was added, over the course of 20 min, 35 mL of a 2.0 M solution of oxalyl chloride in CH2Cl2. The glyoxyl chloride formed immediately and was removed by filtration and washed with 20 mL cold TBME. A solution of 16 mL diethylamine in 50 mL CH2Cl2 was prepared, cooled in an external ice bath, and vigorously stirred. To this, the solid glyoxyl chloride was added in small increments producing a yellow solution. The reaction mixture was washed successively with H2O, 0.5 N HCl, and again with H2O. After drying over anhydrous Na2SO4, the solvent was removed under vacuum providing an orange solid as residue. This was recrystallized from boiling THF and, after filtration and air drying to constant weight, provided N,N-diethyl-2-methylindoleglyoxamide with a mp 170-172 °C.

To a stirred and cooled solution of 7.4 g N,N-diethyl-2-methylindoleglyoxamide in 80 mL dry toluene under an inert atmosphere, there was added 31 mL 65% Red-Al in toluene, at a slow rate. After 20 min the ice bath was removed and the reaction allowed to stir for 2 h, and finally an additional 3 h at 60 °C. The light yellow solution was cooled again in the ice bath, and the excess hydride destroyed by the slow addition of 15 mL IPA followed by 50 mL H2O. The solids were removed by filtration and washed with toluene. The combined filtrate and washings were repeatedly washed with H2O and then extracted twice with 0.5 N HCl. The aqueous extracts were pooled, washed with CH2Cl2, and made basic by the addition of 25% NaOH. The precipitate that formed was extracted into several small portions of CH2Cl2 which were pooled and dried with anhydrous Na2SO4. After removal of the drying agent, the solvent was removed under vacuum. To the residue there was added a 1.0 M solution of HCl in anhydrous Et2O until the mixture was neutral as determined by external damp pH paper. The resulting solid was removed by filtration and twice recrystallized from a MeOH / acetone mixed solvent. There was thus obtained N,N-diethyl-2-methyltryptamine hydrochloride (2-Me-DET) as white crystals with a mp 214-216 °C.

QUALITATIVE COMMENTS : (with 70 mg, orally) "A very subtle onset characterized most notably as a mild stomach ache that lasted a short while. There was a sort of vague unreal feeling at an hour, but my thought pattern seemed to be quite clear. In another hour I noticed that higher pitches of the music on the radio were being muffled and the tones seemed to be shifting to lower frequency. I phoned a friend, and first the dial tone, and then her voice sounded wrong. The sense of touch (the phone receiver) was normal and my conversation flowed easily. Television seems amusing, but perhaps it really was amusing. Soup tasted fine, and there was no appetite suppression. No GI problems, no next-day negatives."

(with 120 mg, orally) "My thoughts became quite cloudy, increasingly so for several hours. And somehow slower than usual. Reading didn't seem to connect, and I had to turn the radio off as it was lousy. Texture, not content. I could type OK, and did, so my body was OK, but things came to me slowly. I wasn't very hungry but food tasted OK. The 'cloudy' was pretty much gone after six hours. I don't particularly want to repeat this, as there isn't much here that I enjoy."

EXTENSIONS AND COMMENTARY : There is an interesting idea tucked away here in what seems to be an uninteresting compound.

The sound distortion, mentioned in both of these reports, brings to mind DIPT where it is the major indicator of intoxication. With some people, it is the only change observed. With DIPT, there are two isopropyl groups on the basic nitrogen atom; here there are two ethyl groups. One might speculate that there might well be some optimum group geometry that would make the auditory to visual distortion ratio as high as possible. There were no suggestions that there were any auditory changes with DET so perhaps the added mass of that methyl group at the 2-position brings the molecular weight into some "auditory window." A compelling compound would be, of course, N,N-diisopropyl-2-methyltryptamine (2-Me-DIPT), but I don't believe that it has ever even been synthesized as of the present moment. It would certainly be a simple compound to make.