What is known of ortho-DOX variants?

[Limpet_Chicken]

What is known of the activity of, by Shulgin's nomenclature system, ortho-DOx variants? ortho-DOT looks inactive, as does the corresponding 3,4-methylenedioxy-2-bromoamphetamine. the TMA-2 doesn't look great either.

But what of amphetamines and phenethylamines having the 3,4-dimethoxy-2-alkyl/alkenyl/alkynyl or having a 2-halo/haloalkyl residue? the DOB positional isomer by rights looks like it should have been looked at, but I can find VERY little data on this substitution pattern.

 

[dread]

3,4-methylenedioxy-2-methyl seems to produce a potent SSRA, so to me it wouldn't seem to be a far stretch to replace that 2-methyl with another nonpolar group and retain activity. The same could work for 3,4-dimethoxy, at least the oxygens are in the same place

But this is all speculation.

 

[Limpet_Chicken]

Yeah I read PIHKALs entry for that one, as well as the 2-bromo.

I'm specifically interested in the methoxy substitutions though in this case, I find it really odd that he makes mention of the ortho-DOB isomer (or might have been the DOM analog) only as a footnote somewhere and afaik it has never been tasted.