Preliminary info on:
2,5-Dimethoxy-p-phenylenebisethylamine dihydrochloride (DMPbisEA)
that's 2,2'-(2,5-dimethoxybenzene-1,4-diyl)diethanamine dihydrochloride
Just a teenage fantasy compound…
The compound was obtained from 1,4-bis(chloromethyl)-2,5-dimethoxybenzene via nucleophilic substitution with KCN and the hydrogenation of the resulting dinitrile. 1H NMR showed the presence of about 10 mol% of an unknown side product (based on MeO groups and aromatic protons). Recrystallization from acetonitrile or acetonitrile/H2O proved impossible because the side product was considerably less soluble than the main product, or so it appeared. No other solvents were tried, so the impure sample was used for the bioassays. The freebase diamine is so polar that it was not possible to extract it from water by using diethyl ether (the ChemDraw calculated LogP for octanol is 0.43!). A triple extraction with ethyl acetate from the aq. solution saturated with NaCl did it. The ethylamine group is terribly hydrophilic, even more so than the methoxy group, and it is known that 2,4,5-trimethoxy-PEA is inactive at < 300mg. Therefore, by analogy, DMPbisEA should be inactive as well. It was nevertheless hoped the symmetry which at least doubles the docking options would compensate some of this loss of hydrophobicity.
Bioassays
10 mg orally: Nothing.
35 mg orally: A solution in orange juice was drunk. After 1:30h there was maybe some threshold activity. Not enough to be sure and not enough to perceive the nature of activity. This lasted up to two hours. If this is truly the threshold then the full dose would appear to be 250-350mg, but at least another trial with a higher dose is needed to confirm whether this was truly a threshold or just placebo effect.