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Chemistry question! Does this substituted phenethylamine varient exist?

Saucy

Saucy

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Joined
Aug 20, 2009
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dimethoxydiethylaminobenzene.png


This molecule is basically 2C-E with an additional amine group bonded to the ethyl chain on carbon-4. Does this molecule exist? I see no reason why it shouldn't, but I can't find any reference to it anywhere, partially because I'm not certain what it would be called.

Because the addition of an amine group would give the molecule cyclic symmetry, would the ethylamine group(s) lose their priority over the benzene ring in naming the compound? My guess at the nomenclature (accompanied by big "fuck you" to IUPAC) would be:

2,5-dimethoxy-1,4-diethylaminobenzene

but I'm honestly not that sure; my chemistry skills are very rusty. Is this molecule plausible? Why or why not? What would the correct name for it be? I know there are a few chemists on bluelight, so if someone would be willing to shed a little light on this for me it would be much appreciated.

Thanks,

-Saucy
 
Good question, I'm impressed :)

Also, the symmetry is really cute! God knows I've puzzled with PEA and tryptamine substitution for years, but this didn't occur... somehow it looks much too good to be true, in similar situations the result was often a certain explanation why it is just not pharmacologically helpful or innovative what you impose.
 
Saucy said:
dimethoxydiethylaminobenzene.png


This molecule is basically 2C-E with an additional amine group bonded to the ethyl chain on carbon-4. Does this molecule exist? I see no reason why it shouldn't, but I can't find any reference to it anywhere, partially because I'm not certain what it would be called.

Because the addition of an amine group would give the molecule cyclic symmetry, would the ethylamine group(s) lose their priority over the benzene ring in naming the compound? My guess at the nomenclature (accompanied by big "fuck you" to IUPAC) would be:

2,5-dimethoxy-1,4-diethylaminobenzene

but I'm honestly not that sure; my chemistry skills are very rusty. Is this molecule plausible? Why or why not? What would the correct name for it be? I know there are a few chemists on bluelight, so if someone would be willing to shed a little light on this for me it would be much appreciated.

Thanks,

-Saucy
Click to expand...

That name is not correct. It should be 2,5-dimethoxy-1,4-di(2-aminoethyl)benzene. It could certainly be made, but I don't think it would be active. There needs to be a non-polar group in the 4 position for good activity.
 
tryp2fun said:
That name is not correct. It should be 2,5-dimethoxy-1,4-di(2-aminoethyl)benzene. It could certainly be made, but I don't think it would be active. There needs to be a non-polar group in the 4 position for good activity.
Click to expand...

Does that always need to be the case? I can think of one active phenethylamine off the top of my head that seems to violate that rule: 2C-T-21, but there probably are more out there, right?
 
its so odd you should post that molecule! as i was just sketching it out a couple weeks ago, it was the symmetry that interested me as well, i dont know if it would be active though....
 
Would you like us to move this to Advanced Drug Discussion? You'll get much more knowledgeable responses in there I suspect. Not that PDers aren't knowledgeable, but ADD specializes in this type of question.

I'll just move it, actually, because it belongs there in fact. Let me know if you feel I have done your thread wrong by my actions. :)

PD -> ADD
 
The compound is known, CAS: 40995-65-1, albeit literature is scarce:

JACS 1949, 71, p.393
J Chem Soc, Perkin Transactions 1: Organic and Bio-Organic Chemistry 1973, No.8, p.832
JACS 1984, 106(13), p.3826

These are all refs that mentioned this compound. Well, not much :\

The only one of those above that mentiones some biological data is the first one:
These amines are devoid of pressor, bronchodilator, or antihistamine activity. They showed less than 10 "ergotrate" activity.
Click to expand...
(taken from the abstract; no more info because ACS's homepage is down at the moment)

- Murphy
 
Morninggloryseeds told us here awhile back that this compound is inactive as psychedelic,I'm not 100% sure though.But I would guess its too polar to cross the BBB.
 
Well, I would think that it's not this much more polar than plain 2C-E. But IIRC there were only uncharged (think NH2 to NH3+ !) residues in the para-position tolerated. I have no info about the activity but it doesn't surprise me that it's inactive.

- Murphy

Edit: Calculated logP-values from this site or this site:
2C-E: 1.805 & 1.62
proposed molecule: -0.126 & 0.13
Well...different, but not much though.
 
Last edited:
Xorkoth said:
Would you like us to move this to Advanced Drug Discussion? You'll get much more knowledgeable responses in there I suspect. Not that PDers aren't knowledgeable, but ADD specializes in this type of question.

I'll just move it, actually, because it belongs there in fact. Let me know if you feel I have done your thread wrong by my actions. :)
Click to expand...

No problem! I actually kinda forgot about ADD when I posted this.
 
Not sure how appropriate or relevant my next question is for this particular thread but the compound above was very recently discussed in the PD Social thread, a bioassay unsurprisingly produced no effects.

But my question is: what would be the expected activity of a secondary amine substitution such as 2,5-dimethoxy-4-methylamino-phenethylamine or 2,5-dimethoxy-4-ethylamino-phenethylamine?
The 2C-O series was not thought to be fruitful but what is the big difference with the 2C-T series? Is it the electronegativity / δ- or is it the different binding angle, 110 degrees vs 90 degrees?
So if sulfur works but not oxygen, then what about nitrogen? Something tells me it works even less than 2C-O-x ?
 
I think I remember reading about amide substitutents at the 4-position (i.e. 4-acetylamido-2,5,-DM-phenehylamine) - I can't remember if they were active or not though, I believe they weren't. Not sure that actually correlates to anything meaningful on a secondary amine though.

Another consideration is that aromatic amines are usually pretty hard on the liver.
 
Solipsis said:
Not sure how appropriate or relevant my next question is for this particular thread but the compound above was very recently discussed in the PD Social thread, a bioassay unsurprisingly produced no effects.

But my question is: what would be the expected activity of a secondary amine substitution such as 2,5-dimethoxy-4-methylamino-phenethylamine or 2,5-dimethoxy-4-ethylamino-phenethylamine?
The 2C-O series was not thought to be fruitful but what is the big difference with the 2C-T series? Is it the electronegativity / δ- or is it the different binding angle, 110 degrees vs 90 degrees?
So if sulfur works but not oxygen, then what about nitrogen? Something tells me it works even less than 2C-O-x ?
Click to expand...

Positive charge at pH=7 in the four position probably yields poor binding... Generally for the 2C compounds 4-position requires steric bulk with low electronegativity atoms for activity. The only other (weakly) active compounds like 2C-N are electron withdrawing. Perhaps the primary effect is with steric bulk and the secondary effect is with charge (neutral being most active, -'ve being less active). But that's speculation.
 
Just going on instinct but I would guess the second amine would mess w/ its ability to readily cross the BBB...cool idea though
 
Make the 4-substitution too long (similar to 2C-Bu in length, so probably an antagonist on that basis alone, let alone whether the polarity & HBA/HBD activity there interfere with that binding region), or ruin binding at the traditional amine (N-methylated derivatives are much reduced in activity) region.
 
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