O-methylation of paracetamol, hydrolysis of the amide, and gas phase reaction with glycol and a Cu/SiO2 catalyst might possibly be feasible to 5MeO indole. At least, Cu/SiO2 works for straight indole see http://www.imm.ac.cn/journal/ccl/1303/1303009-211-01-381-p2.pdf and mechanism http://www.scientific.net/AMR.287-290.120 it would stink though, if indole's reputation is to be trusted.
There also exists the fascinating title "Disproportionative Condensations. IV. The 3-Alkylation of Indoles by Primary and Secondary Alcohols" which leads me to suggest that glycol might be reacted with indole to form tryptophol, dimethylaminoethanol, and the product of an alkali metal in alcohol, iPOH likely, reduction of proline, and perhaps other interesting alcohols might be.
Epinephrine might be trimethylated at the phenols and beta-hydroxyl to something notable. http://www.nrcresearchpress.com/doi/pdf/10.1139/v65-332 might be worth a read: "Adrenaline methyl ether... has recently been reported to produce considerable stimulation of the central nervous system; however, it was much less active than adrenaline peripherally (1, 2)." The trimethyl ether is also known, as seems to be the methylenedioxy.
The demethylation procedure of quaternary ammonium acetates is apparently well known, but is there public record of it having been tried on tryptamine? Dimethyl sulfate, while discouragingly poisonous, would have the advantage of forming gypsum with calcium acetate.
It probably wouldn't be feasible but I wonder if there's some way to derive racetams from povidone.
If anhydrous aluminum chloride sublimates at all easily, perhaps a thermite type reaction with a more easily dehydrated metal chloride would be easier than some of the other suggestions like gassing molten Al with chlorine.
Triclosan, the ubiquitous antibacterial, with some trouble might be converted with copper and lye to trihydroxybenzene, although the aryl chlorides might be unhealthful so longer reaction times and separation would be best.
There also exists the fascinating title "Disproportionative Condensations. IV. The 3-Alkylation of Indoles by Primary and Secondary Alcohols" which leads me to suggest that glycol might be reacted with indole to form tryptophol, dimethylaminoethanol, and the product of an alkali metal in alcohol, iPOH likely, reduction of proline, and perhaps other interesting alcohols might be.
Epinephrine might be trimethylated at the phenols and beta-hydroxyl to something notable. http://www.nrcresearchpress.com/doi/pdf/10.1139/v65-332 might be worth a read: "Adrenaline methyl ether... has recently been reported to produce considerable stimulation of the central nervous system; however, it was much less active than adrenaline peripherally (1, 2)." The trimethyl ether is also known, as seems to be the methylenedioxy.
The demethylation procedure of quaternary ammonium acetates is apparently well known, but is there public record of it having been tried on tryptamine? Dimethyl sulfate, while discouragingly poisonous, would have the advantage of forming gypsum with calcium acetate.
It probably wouldn't be feasible but I wonder if there's some way to derive racetams from povidone.
If anhydrous aluminum chloride sublimates at all easily, perhaps a thermite type reaction with a more easily dehydrated metal chloride would be easier than some of the other suggestions like gassing molten Al with chlorine.
Triclosan, the ubiquitous antibacterial, with some trouble might be converted with copper and lye to trihydroxybenzene, although the aryl chlorides might be unhealthful so longer reaction times and separation would be best.
