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

rickolasnice

rickolasnice

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Any info?

Speculative ideas?

That in at the begining of title isn't supposed to be there!
 
That's the thiophene-bioisoster of methamphetamine.

The amphetamine-congener was reported to be active, with a potency somewhat higher than amphetamine. Peripheral sideeffects (vasoconstriction) were mentioned as side-effects, as well as bad body-smell after repeated use.

I'd bet that the compound in question should be active, too. It should also share the (neuro)toxic effects of methamphetamine. Therefore, I can't really recommend this one.

PEACE! - Murphy
 
Have I got this the correct way around?

If so, would this be a whole series of compounds that could be explored? I.e the mescaline equivalent as detailed...?
 

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thanks, ok so something more like this?

Quite excited, was thinking there was a serious lack of starting blocks as PEA + tryptamines have been thoroughly explored.

Could we maybe get some mescaline analogue as in picture??

Whole new lead of compounds??!8o
 

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I remember discussing thiophen as a replacement to benzene but could this be used as a completely novel starting material?

What about the MDMA analogue of thiophen?! 8o

Also just twigged how duloxetine is essentially fluoxetine with a thiophen replacement (+Naphthalene instead of CF3-Benz) for the benzene ring, cool!
 

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LSDMDMA&8489422 said:
could i has the 3rd one you posted a pic of plz?
Click to expand...

just RIGHT click SAVE TARGET AS

just realised actually I drew it without the alpha-methyl, I can't seem to add attachments any more so can't correct it.

You planning on publishing on another forum! steeling my genius ideas hey 8) ;)
 
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@Phener: In all your structures is the thiophene not correct. Sulfur has only two bonds in this case!

Furthermore would the mescaline-analogue look different, i.e. 2-(3,4,5-trimethoxythiophene-2-yl)ethylamine. See the picture below.



I doubt heavily that the mescaline- & the MDMA-analogue possess any viable activty. The ring's geometry is far too different.
As said before, the amphetamine-analogue was tested and proved to be slightly more potent than amphetamine itself. Side-effects on the other had were discouraging.


Peace! - Murphy
 
Some 4-alkylated/halogenated 2c:s could possibly be made into thiophene analogues. The methoxy groups being on the 2 and 4 carbons of the thiophene while the "para" substitution being on the 3-carbon, it should be reasonably close to the configuration of 2c:s... close enough to fit in the 5ht2a receptor, possibly.
 
Like this:

thio2c.png
 
dread said:
it should be reasonably close to the configuration of 2c:s... close enough to fit in the 5ht2a receptor, possibly.
Click to expand...

I agree with Murphy, I would be very surprised if these compounds fit into 5-HT2A binding pocket well. The 2-methoxyl seems to barely interact in the regular 2C-x/DOx, if at all, because it can't reach the serine now making the ring smaller seems to me wouldn't help the situation. If this was changed into a benzothiophene ringed basis to compare with tryptamines I'd have a bit higher hopes for it but even then changing nitrogen for sulfur loses the interaction capability. Oxygen replacing nitrogen in the indole body of DMT (dimemebf) decreased 5-HT2A activity. It'd require more than a quick fix to turn this into a psychedelic.

On a last note thiophene-2-ethylamine resembles histamine very closely, methoxylating it makes me wonder if it'd move towards histaminergic activity more.
 
On a last note thiophene-2-ethylamine resembles histamine very closely, methoxylating it makes me wonder if it'd move towards histaminergic activity more.
Click to expand...

Yeah, that would definitely be a possibility...

Still, if someone made it, I might try it, just out of curiosity...

The 2-meo may not even be totally necessary for binding. I mean if you remove it from DOM you get MMA which still retains some psychedelic activity.
 
Astavats said:
I agree with Murphy, I would be very surprised if these compounds fit into 5-HT2A binding pocket well. The 2-methoxyl seems to barely interact in the regular 2C-x/DOx, if at all, because it can't reach the serine now making the ring smaller seems to me wouldn't help the situation. If this was changed into a benzothiophene ringed basis to compare with tryptamines I'd have a bit higher hopes for it but even then changing nitrogen for sulfur loses the interaction capability. Oxygen replacing nitrogen in the indole body of DMT (dimemebf) decreased 5-HT2A activity. It'd require more than a quick fix to turn this into a psychedelic.
Click to expand...
My reasoning against the MDMA- & mescaline-analogues stems almost exclusively from the different geometries. The sizes on the other hand should be comparable! Don't forget that sulfur is in one period below carbon, oxygen and nitrogen, and therefore, it is significantly larger. Thus, a thiophene (5-ring) is approx. as big as a phenyl (6-ring).


Astavats said:
On a last note thiophene-2-ethylamine resembles histamine very closely, methoxylating it makes me wonder if it'd move towards histaminergic activity more.
Click to expand...
For histaminergic activity I would think that the rings need to be basic (as in imidazole or pyrazole).


Peace! - Murphy
 
My mistake, thanks Murphy. Logically it makes sense sulfur would increase the ring size, which I considered, but I went with the 3D display by MarvinSketch online chemical editor in my response, which I guess is not a completely true representation. I'm still in lower chemistry (pre-OChem) and learning, please excuse my misunderstandings.

dread said:
The 2-meo may not even be totally necessary for binding.
Click to expand...

I agree as far as my understanding of the binding goes however, it could not hurt to improve the methoxyl into something longer and/or stronger to help align the whole compound. There are a lot of imaginative substitute options but I'm not yet knowledgeable in pharmacokinetics enough to know if they would be metabolized immediately or some other problematic issue. Anyway, I've gone off topic.
 
^Thanks for the correction Murphy :)

Ever since loosing my copy of chemdraw, using rubbish WINDRAW :X completely rubbish application.

Is there a limit for early bluelighters in terms of uploading files? My user limit has not exceeded but the upload function has dissappeared. Annoying as I used to be proper user (ex RemB) but lost my password.

Re binding: Surely binding may be COMPLETELY different but as a whole starting compound ala PEA, if only a shulgin had more time (I would vote immortality for the guy! :D) he could surely find the equivalent of the magic 4-position.

Looking at the structure I am wondering whether the mescaline equivalent wouldn't work but a simply Dimethoxy might get somewhere, and certainly the MDMA might (not necessary MDMA equivalent) but some level of 5ht binding?
 
These thread titles could be further encrypted by the use of non-Roman alphabets. For example, Cyrillic:

N-метил-1-(2-тиофена)-2-аминпропан гидрохлорид
Click to expand...
 
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