What about symmetrical 2C?

[Mjäll]

What if one would put another ethylamine on the 4 of 2C?

Is there an obvious reason this hasn't been explored?

There are other 2C's with N atoms in the 4 substitutions.

And the same question(s) about other phenethylamine variants, while we're at it.

 

[Skorpio]

What if one would put another ethylamine on the 4 of 2C?

Is there an obvious reason this hasn't been explored?

There are other 2C's with N atoms in the 4 substitutions.

And the same question(s) about other phenethylamine variants, while we're at it.

I'm not sure it would be too active. The 2C compounds with Ns in the 4 position usually have a nitro group, where the 2 oxygens attached to the nitrogen make it pretty electronegative. I am not sure if there is a 2CX compound with an amine at the 4 position.

 

[Mjäll]

I'm not sure it would be too active. The 2C compounds with Ns in the 4 position usually have a nitro group, where the 2 oxygens attached to the nitrogen make it pretty electronegative. I am not sure if there is a 2CX compound with an amine at the 4 position.

No there aren't any. I checked the list. Thanks a lot for your explanation. It makes sense to me, in as far as i understand the relevant chemistry.

Can you tell me if this type of question is too basic or simple to warrant a thread?

 

[realgar]

What if one would put another ethylamine on the 4 of 2C?

Is there an obvious reason this hasn't been explored?

The compound was prepared by Demonic (hyperlab.info). He posted an outline of the synthesis without experimental details and reported pleliminary bioassays in 2009 (no activity up to 35 mg p/o).

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.

 

[Skorpio]

No there aren't any. I checked the list. Thanks a lot for your explanation. It makes sense to me, in as far as i understand the relevany chemistry.

Can you tell me if this type of question is too basic or simple to warrant a thread?

No, it's perfect for this forum.

Even though its a simple question, you learned something from it. And that makes it worthwhile.

Now I wanna go scour pihkal and see if I can find trends for 2C activity wrt the 4 position.

 

[izo]

I think the 4 position only prefers lipophilic and sterically not to big substitutions.

 

[Fertile]

2CP & 2C-O-4 suggests that their is a fair amount of space at 4. The PEAs and indole derivatives overlay with the 7 position of the indoles overlaying the 4 position of PEAs. Sadly, it's a total b*tch to make 7-substituted indoles and so it hasn't been explored much. 7-methyl AMT is VERY nice - half way between AMT and MDMA.