I don't know about anyone else, but one thing has always intrigued me - Escaline
I'm not sure why, it just grabbed my attention quite a long time ago... Several times stronger than mescaline, made by brominating vanillin and then treating the 5-bromovanillin with Cu/MeOH/etc (http://www.erowid.org/archive/rhodium/chemistry/345-tmba.html) to give 3,5-dimethoxy-4-hydroxybenzaldehyde. Now, with that in hand, it shouldn't be too hard to work out how to get the rest done with either EtCl/EtBr. From there, return to PiHKaL:
Now, read it carefully, the yields are pretty high considering just how readily available most of the intermediates actually are (nitroethane is hard to find, nitromethane not so hard). Reduction of the nitrostyrene to the phenethylamine is going to be an incredibly difficult chore (or maybe not
). However, as vanillin, nitromethane, methanol (comes with every variant of nitromethane I've ever seen) and to an extent bromine are available, you'd think you'd see more of this - especially since Shulgin wrote (@2.1.7) about the fact it is similar to Mescaline without the taste/nausea problem at 40-60mg (also discussed here). Then again, depends what people are after really, a nice, cruise/laugh or dancing like a maniac... Personally I've always preferred acid to E's, so this one always appealed.
I'm not sure why, it just grabbed my attention quite a long time ago... Several times stronger than mescaline, made by brominating vanillin and then treating the 5-bromovanillin with Cu/MeOH/etc (http://www.erowid.org/archive/rhodium/chemistry/345-tmba.html) to give 3,5-dimethoxy-4-hydroxybenzaldehyde. Now, with that in hand, it shouldn't be too hard to work out how to get the rest done with either EtCl/EtBr. From there, return to PiHKaL:
Quote
A solution of 14.7 g 3,5-dimethoxy-4-ethoxybenzaldehyde and 7.2 mL nitromethane in 50 mL glacial acetic acid was treated with 4.4 g anhydrous am-monium acetate and held at reflux for 30 min. Cooling the reaction allowed the formation of yellow crystals which were removed by filtration and washed sparingly with cold acetic acid. The dried 3,5-dimethoxy-4-ethoxy-beta-nitrostyrene weighed 11.5 g and melted at 108-109 °C after recrystallization from EtOH Anal. (C12H15NO5) C,H. Alternately, this product may be prepared from 3.9 g. 3,5-dimethoxy-4-ethoxybenzaldehyde in 60 mL nitromethane containing 0.7 g ammonium acetate and heated on a steam bath for 1 h. The solvent was removed under vacuum, and the residue dissolved in a minimum of hot MeOH. Cooling provided, after filtration and air drying, 2.3 g of bright yellow crystals of 3,5-dimethoxy-4-ethoxy-beta-nitrostyrene, with a mp of 105-107 °C.
Now, read it carefully, the yields are pretty high considering just how readily available most of the intermediates actually are (nitroethane is hard to find, nitromethane not so hard). Reduction of the nitrostyrene to the phenethylamine is going to be an incredibly difficult chore (or maybe not
). However, as vanillin, nitromethane, methanol (comes with every variant of nitromethane I've ever seen) and to an extent bromine are available, you'd think you'd see more of this - especially since Shulgin wrote (@2.1.7) about the fact it is similar to Mescaline without the taste/nausea problem at 40-60mg (also discussed here). Then again, depends what people are after really, a nice, cruise/laugh or dancing like a maniac... Personally I've always preferred acid to E's, so this one always appealed.