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inN-methyl-1-thiophen-2-ylpropan-2-ame hydrochloride

baha. when i asked for the 3rd one, i meant synth some and hook me up lulz. not that i watned the pic.
 
Setting aside size/geometric matters, couldn't the lone pairs on the sulphur somehow imitate the methoxy group of the benzene 2C's? I know I'm associating loosely but since we haven't even bioassayed one of them, I feel confident in that brainstorming. Hint: the increased dopaminergic action of the thiophen isosters versus phenyl must have some reason.
 
If you like lots of different atoms in your drugs, then go for 1-(2-thienyl)-2-methylamino-1-propanone, the thienyl version of methcathinone!


Hint: the increased dopaminergic action of the thiophen isosters versus phenyl must have some reason.
Click to expand...

Well the thiophen ring must be more attuned to interact with VMAT than phenyl. Note TCP has more dopaminergic activity than PCP and the only change in structure is replacing a phenyl with a 2-thienyl (even works in opioids eg the thiambutenes as methadone compounds)
 
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hugo24 said:
Setting aside size/geometric matters, couldn't the lone pairs on the sulphur somehow imitate the methoxy group of the benzene 2C's?[1] I know I'm associating loosely but since we haven't even bioassayed one of them [2], I feel confident in that brainstorming. Hint: the increased dopaminergic action of the thiophen isosters versus phenyl must have some reason.
Click to expand...

[1] Why not? This could be answered by some proper docking studies. I'm sure we have folks around who know how to do this; the question is if they got the sparetime and the verve ;)

[2] Bioassays are available for the amphetamine-analogue and possibly for the methamphetamine-analogue, too, in the Hyperlab. Learn some russian and report back! *giggle*


Peace! - Murphy
 
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1) well f&b doesen't go very deep here lol
the thiophen ring must be more attuned to interact with VMAT than phenyl
Click to expand...
 but my view is that these ligands often do have a certain structurally similar feature taken from the transmitter which is increasing its activity (like the 3,4-Dichloro, or in the serotonin world a 3 or 4 OMe or OCF3 etc). So I speculated that its mainly the Sulfur in the Thiophen doing this particular contribution. Or wait, it might even come to that sensitive beta- position along the other catecholamines!? Fertile ground for research...

2) yes I know those trials, thinking that I'm close to try it for myself soon (hopefully its also active in non russianspeekers =D ) but I meant the methoxylated thiophen analogs, an entire new area I think but I don't have any Scifinder anymore. Fertile ground oops I repeat myself...

As for the title compound itself, I'm not too drawn back because of its cardiovasculars (huh, sulphur mimicking NA?), a good recreational stimulant has to rock a bit. What I'm not believing is the increased smell, this might be psychologically induced because of the sulphur atom present. At least I don't think the thiophen ring gets torn apart metabolically and thiophens itself often smell quite nice...
 
N-methyl-1-(4-(trifluoromethyl)thiophen-2-yl)propan-2-amine seems like a good option, it would lean more to the serotonin side and become better balanced.
 
Perhaps some strong serotonergic neurotoxicity and cardiac valve destruction, too, a la norfenfluramine.
 
nuke said:
Perhaps some strong serotonergic neurotoxicity and cardiac valve destruction, too, a la norfenfluramine.
Click to expand...

I'd say at this point you can't even make that link, completely different structure that can't be compared.

Still if only there were 100 shulgins out there. :\
 
just realised tiagabine has the two 3-methylthiophen-2-yl groups which no doubt act much as BENZYL groups would.

http://en.wikipedia.org/wiki/Tiagabine Wonder why they went for 3-methylthiophen-2-yl groups over benzyl?

Still made me think if the 3-methylthiophen-2-yl, I.e the 3-methyl part is a better comparison to benzyl? Answering my own question: May well have gone with that substitution to prevent metabolic attack at thosepoints. (although could of course simply be better binding profile, half-life, absorbtion, they have the BIG bucks to test all these different things, not that I am jealous 8))
 
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