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indole "phenibut" analogues: SAR theorization needed?

G

gladiolus

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Dec 29, 2007
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Hi all,
I've been given to thinking about the much [western] dismissed compound of phenibut, how it really it pretty a remarkable substance. Those of you who disagree with me, about how it modifies the basic PEA structure should probably turn away now!LOL

Anyhow, what if you made a very similar structure, preserving the GABA structure, but adjoined it to the alpha part of PEA? resulting in an alpha- propanioc-PEA? Has any research been done on this? What would you expect?

Another thing that got me thinking was how about using the indole instead of the phenol and try the indole analogue beta-aceto tryptamine? or indeed alpha-propanoic-tryptamine? We know that AMT and AET are active, probably APT as well,- I think I read something negative about APT once, but can't quite recall where. But would APoT(alpha-propanioc tryptamine) be worth a try given it's extra GABA molecule present?

Can't get these speculations out of my mind and I would love some advanced pharmacological-types to comment either positively or negatively about these molecular proposals.

Cheers,
 
what with the baclofen hype this is indeed a very interesting avenue. Always wondered with baclofen why did they choose clorine? Synthesis or did they compare F, B, etc:\
 
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As for phenibut analogues, I'm interested in 4-phenyl-2-pyrrolidone, the lactam of phenibut. By the GBL logic it should metabolize to phenibut...
 
I have a horrible intuition about the alpha-methyl phenibut: thanks for your reply though, I remember reading your original post. I can imagine the alpha-methyl on this making a more sickly and noxious compound, the type of thing with extended nausea and vomiting. I can't say I have the same intuition about the alpha-propanoic PEA (type 2 phenibut): I think this might be very promising - I can imagine a more stimulant-effect coming through from the PEA molecule, as well as it being more readily aborbed, especially if using a dextro-form. Might be too similar to amph to generally circulate though.

But the main point: how about the indole/ tryptamine molecule being tinkered with in the same way? It might show mild hallucinogenic activity givin its aceto-position at the beta tryptamine site [given that the beta-aceto on the PEA significantly modifies its activity]. Given that alcoholism shows a great interaction between the GABA and serotonin receptors, this particular fusing might well prove useful as an anti-craving agent and a possible antidepressant.

Geez, someone needs to follow up on TihKaL with some of these new crazy perspectives people have, dont you think? Like how about replacing the nitrogen atome in the indole of n,n-DMT with an oxygen atome, making DMT's benzofuran analogue?
 
Thats what I was thinking :')
But what is so horrible about pentylone?

What I find confusing is that they jumped from methylone - ethylone to butylone which points to the 'aliphatic' chain bit all of a sudden. Anyway those trivials names have always worked for me, pretty acceptable.

But I sense a hypocritical trend in myself, many popular names coined nowadays I reject for some reason or another but the ones that already existed when I came along and did my literature research for fun and informing preparation, those 'old' ones I mostly accept as established.

Do you think the names nowadays are that much more moronic or do you think many have this same hypocrisy?
 
^ LOL exactly!

Solipsis: I think the reason you and many of us reject these new names because many of them were created by vendors to woo kids (and adults :|) into buying them following Mephedrone's success.

For example, "Buphedrone" is very clearly a cash-in on Meph, because in all the "-ephedrones" the suffix is taken from the 4-substitution. The "Bu" in Buphedrone is taken from the alpha-substitution.

Or "Naphyrone" - it sounds like a Meph analogue, when in fact it is closer to MDPV.
 
shulgin...did some nonsensical things coining nomenclature too. I think that any set of 'Latinized' continuous word derivatives of some parent structure will run into inconsistencies, particularly when prefixes and suffixes attach to different substitutions for different compounds....or when different parent skeletons are used. Hell, Shilgin's letter-soup ran into enough inconsistencies already.
 
Back to the subject of phenibut analogues, does anyone have any further information about 4-phenyl-2-pyrrolidone?

I found a MSDS of it, claiming it to be a muscle relaxant and analgesic in some unspecified mammals, but am not aware of any human bioassays...

Also I stumbled upon a site offering 4-chloro and 4-fluoro analogues of it... the 4-chloro would be the lactam analogue of baclofen, and a possible baclofen prodrug? Intriguing.
 
anyone able to get access to this document?

Synthesis of novel pyrrolidin-2-ones: -aminobutyric acid cyclic analogues
S. Al Akoum Ebrik 1, B. Rigo 1, C. Vaccher 2, M-P. Vaccher 2, N. Flouquet 2, M. Debaert 2, P. Berthelot 2
1Laboratoire de Chimie Organique et Environnement, Ecole des Hautes Etudes Industrielles, 13 rue de Toul, 59046 Lille, France
2Laboratoire de Pharmacie Chimique et Chimie Thérapeutique, Faculté des Sciences Pharmaceutiques et Biologiques, 3 rue du Professeur Laguesse, 59006 Lille, France

This work was performed in the Laboratoire de Pharmacie Chimique et Chimie Thérapeutique.
Funded by:
ADIR and Co


Abstract
Some new N-substituted pyrrolidin-2-ones, cyclic analogues of baclofen and of 3-(5-methoxybenzo-furan-2-yl)--aminobutyric acid, have been prepared and characterized, starting from 4-(4-chlorophenyl)-pyrrolidin-2-one and 4-(5-methoxybenzofuran-2-yl)pyrrolidin-2-one.
Click to expand...


http://www3.interscience.wiley.com/journal/122251092/abstract?CRETRY=1&SRETRY=0
 
^ I'd like to see that, too.

Btw I also remember seeing something about the lactam analogues of gabapentin and pregabalin... but I think they were mainly used for precursors or something.
 
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