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  • N&PD Moderators: Skorpio

Arylcyclopentylamines

I believe you really need a six-membered ring. It need not be a cyclohexyl derivative, six-membered heterocycles have also been studied.

I believe it's something to do with the relative position of the N: and the aromatic. It's worth reading how MK-801 (Dizocilpine) identified those two values.
 
pubchem.ncbi.nlm.nih.gov

1-(1-Phenylcyclopentyl)piperidine

1-(1-Phenylcyclopentyl)piperidine | C16H23N | CID 13015299 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.
pubchem.ncbi.nlm.nih.gov pubchem.ncbi.nlm.nih.gov
 
There's a chance it could still work but it doesn't make it an improvement.

I know that piperidine homologs of fentanyl and methylphenidate were only very poor at binding to the receptors.

But as for pcp homologs i've not looked into it recently. I know you are talking about the cycloalkyl portion and not the amine function here though.

Also with Troparil, I remember they made an analog where they changed the ring to 7-azanorbornane and only conjured a molecule with very poor activity.

So what I am basically saying is that even though I don't know the answer to the OP's q, i've seen examples in the literature where there is an optimal ring size with very poor flexibility.

I think I remember reading that pcp had a lot of flexibility to changing the substituents but I have forgotten about it.
 
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Did I post that link to the French researchers who replaced the cyclohexane moiety for a 4-thiane? Because they also showed that the ketone found on some examples seems to be space-filling and nothing more. They were able to replace the ketone with methyl groups which obviously leads to an extra optical centre and yep, they resolve them to find which was the more active.

I mean, totally impractical but they made dozens of examples. But they only used thiophene as the aromatic as I assume they were solely looking at that 6-membered ring and tiletamine was their reference.
 
See this also: https://en.wikipedia.org/wiki/Ketamir-2
250px-Ketamir_structure.png
 
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