Yup, 2-hydroxy-5-methoxy-t-butylbenzene/2-methoxy-5-hydroxy-t-butylbenzene whichever fucking isomer it is won't matter squat once it's methylated on both OH groups now will it?

Check out that substitution... 2,5-methoxy would not be exactly difficult (very easily imagined, or dreamed of, in you will)... Available in huge quantities for food processing (ie. pure) as an anti-oxidant.

But that fucking t-Butyl group... What to do with that sucker? What would it oxidize to? Assuming, of course, that the oxidation could be made to affect the exposed ends of the methyl carbons (of the t-butyl chain) rather than causing ring-cleavage... If so, how to utilise selective oxidation/halogenation to get to our beloved isopropylamine?

Alternatively, 4-alkyl-2,5-dimethoxygroups are winners, although Shulgin did not test any bent-chain alkyl groups (and they don't get more twisted than a t-butyl, at least not for size), but the good Dr stated that DOET (4-ethyl-2,5-dimethoxy-amphetamine) is a good experience (+++ @ 5mg), so given that the t-butyl group could be viewed as being only 2-carbons long (with 2 substituted carbons hanging off them), it MIGHT be a worthwhile way to utilize the substance...

Is 4-t-butyl-2,5-dimethoxyphenethylamine (or amphetamine) active? what is the radius of the group compared to an iodo group? IIRC the isopropyl substitution is active.

Is 4-t-butyl-2,5-dimethoxyphenethylamine (or amphetamine) active? what is the radius of the group compared to an iodo group? IIRC the isopropyl substitution is active.

I'm not sure, there are SAR's that suggest branching (Nichols (also here), Glennon and even  [Shulgin) . But the t-butyl group  (ie.DOTB) - looked at in one way, it is a disubstituted 4-ethyl (the best results are with this from memory) benzene... The bulkiness of the t-butyl group might be bad, but then again, the bulkiness of the TFA group @ the same position didn't seem to hurt activity did it (in fact the t-butyl seems almost like an analogue of the TFA substituted compounds, especially structurally)... It should certainly slow down enzymatic hydroxylation @the 4-position and is hydrophobic as all get out...

It might be worthwhile searching the literature... The fact it don't work on Rats don't necessarily mean shit... Then again, those papers give me evil thoughts with regard to ibuprofen...

4 propyl 2,5 methoxy amphetamine is active 
so is the allyl and the methyl subst.

why not this one ?

I would belive its kinda like DOM though strenght that would be another thing.

good f***ing point man you are one sharp guy!!!
but i also think the main diff is electro negativity at the para position so this may imply a different pharmacodynamic mechanism than the typical dox compounds ie. p-nitro, p-brom, p-iodo, etc.

Please, let's try to keep this thread on topic. No, I doubt you guys are thinking along the same lines. The compound won't be a good stimulant.

Decarboxylation of that sidechain to give the styrene/ethylbenzene on that side, then try and work out a way to oxidize the sec(?)-butyl sidechain on the other side to a carboxylic acid...

Given the ease of access to the precursor, that may not be too bad a thing, I mean, MDA/MDMA require 100mg type doses, so it wouldn't be too big a hardship...

I also recall (Cannot recall exactly where) that the DOTB tends to be more of a stimulant than a true-blue hallucinogen, which makes me wonder which stereoisomer would be the active one - from memory, the (R) isomer is active in the Hallucinogens and the (S) isomer in the stimulants, if it is the (S) isomer that is active, that would available directly from l-alanine (available from every health food shop on the planet).

The other alternative would entail working out how to modify the t-butyl sidechain to get to where we want - I don't know, oxidation to carboxylic acids, whatever... Anything to shorten that chain to something useful

If one could resolve isomers, a Reimer–Tiemann could be performed, and everything is cake from there.