Tryptamines of DOx

[jibby jab]

Is it possible to make the DOx of tryptamines, as in using alpha-methyltryptamine as the base to create some novel compounds? For example DOC (2,5-Dimethoxy-4-chloroamphetamine) would be 2,5-Dimethoxy-4-chloroAMT.

If they already exist could someone point me in the right direction? Cheers.

 

[Solipsis]

Sorry

2,5-Dimethoxy-4-Chloro-AMT does not make sense, because the 2,5 and 4 designate positions that are in the DOX molecules (well, on the phenethylamine phenylring).

AMT has 2,4 and 5 positions but putting any similar groups there like methoxy or chloro groups would not be expected to make an active drug at all.

Look at the AMT molecule I attached, there are some things possible to hang on this molecule.

1 (N) - put anything on it and it will be much less potent or will not work
2 also a bad idea apparently
3 cannot put anything on here because all carbon bonds are taken up!
4 something like a hydroxy or acetoxy may be put here but I have read about effects that indicated toxicity
5 methoxy, put that on it and you have the existing drug 5-MeO-AMT

Considering 5-F-DMT appears to be an active drug it may be possible to attach a fluoride on the 5-position on AMT and get 5-fluoro-AMT or 5-F-AMT. It might be nice.

But nothing DOX-like is possible because they just have a really different build.

I don't know what would happen if you tried to put a chloro on the 6-position and a methoxy on the 5 though. That might come closest to what you are talking about. Perhaps another methoxy on the 7?

All these groups would probably prevent the molecule from docking into the receptor correctly but I would have to see how it docks again.

 

[jibby jab]

Thanks for clarifying solipsis. I don’t have a grasp on chemistry and I was just wondering if it was possible.

 

[Solipsis]

OK no problem, I always have a hard time giving a simple answer to a complex question.

But to sum up:
- technically you could make something that would look like it
- the numbers would be different because you just number the positions in the molecules differently
- it would probably not work at all

To indulge your fantasy it would look like something similar to this attachment below:

4,7-dimethoxy-6-chloro-α-methyltryptamine

 

[the outsider]

Yeah it makes sense: alpha,N,N-trimethyltryptamine (which I believe has been tasted & is active a la AMT). Don't see why 4-hydroxy & 5-methoxy variants wouldn't be either. You could then add various alkyl substituents on the nitrogen.

Hopefully you can picture those, I don't have chemdraw so I can't upload diagrams.

 

[Bomboclat]

This would probably do better over in ADD.

My .02
I wish I could contribute a bit more

 

[stom10]

Ignoring the 2, 4, and 5 substitutions and just assuming you mean the alpha-methylated versions of already known psychedelic tryptamines, you may find some active compounds. The problem is that, while phenethylamines don't have any N substitution, the active tryptamines are N,N-dialkyl substituted, meaning that the alpha methyl group would add steric hindrance and bulk to an already bulky section of the molecule. I'm not sure how this may affect the possible pharmacology of these compounds. I think they may not be as explored as the alpha methylated phenethylamines is because there simply isn't any chemical justification for doing so, aside from misguided extrapolation from the phenethylamines.

 

[fractal fountain]

Would n,n-dialkylated substituted alpha-methyl tryptamines be active/worth synthesizing? Various experimentations, even just one methyl group on the nitrogen?

Or would these sorts of things as the above poster says, be 'too bulky'?

 

[Solipsis]

AMT with only one methyl group on the nitrogen is alpha,N-DMT. Check here in tihkal! And here is it's 5-MeO analogue
If the word DMT confuses you remember it means dimethyltryptamine and to be exact is N,N-DMT, two methyls both on the N(itrogen).
AMT has only one and its on the alpha.
Alpha,N,N-TMT is discussed here.

To be honest it all doesn't really sound like it would be promising to continue in those directions. Loss of potency and no real nice psychedelic effects as far as I can see.

Not sure but trying to hybridize it with a PEA molecule a la DOX or mescaline might just not work because you either try to mimic one neurotransmitter or its (modulated) effects on corresponding receptors or the other.

It's the same problem I stumbled on when I was wondering about psychedelic-stimulant hybrids: if you try to combine two different mechanisms of action you get a good chance of messing up both instead.
Though if you hit the jackpot who knows??

 

[atara]

The pyrrolidine ring in lucigenol seems like the most promising direction for new tryptamines, IMO. I wonder what you'd get sticking some things on the ring or extending the N-methyl.