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Conformational equilibra of hydrochloride salts of pethidine, ketobemidone, and related central analgesics of the 4-arylpiperidine class

Fertile

Bluelighter
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Mar 31, 2022
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The paper in the title notes that the piperidine exists primarily in the chair conformation. That explains why AP-237 gave AP238 which is a simplification of azapricin - the azapricin bridge forcing the chair conformation.

But considering the increase in potency the bridge provides and their are early reports of bridged pethidine derivatives being more potent.

I note that compounds of the phenylpiperidine class with an N-(E)-3-Phenylprop-2-enyl moiety and the p-Nitro inreasing potency. But an N-propenyl with a gamma -OH was even more potent but would not preclude the p-NO2.

It's NEVER going to be that potent but phenoperidine is x60M and uses a totally different set of precursors.

But it IS another detail. If that bridge could be added - would x600M be possible?

THAT would give fentanyl a run for it's money.
 
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