Name Reactiond

[Feretile]

There are a few hundred name-reactions and their beauty is their scope. They will more or less work with ANY precursors one chooses. Yields may vary, workup may be more or less complex BUT they reliably produce the desired product.

Many moons ago found 2 papers discussing Dimethylaminopivalophenone (not my name) and realised, after some work with ChemOffice, that it overlays pethidine (demerol) and has just about the same activity.

But it's a sheme nobody has looked at this (the prototype) and worked on analogues with more activity.

 

[Skorpio]

I wonder what a cyclopropyl on the 2 position would do? Do you think it be too rigid or possibly reactive a la trancypromine?

 

[Feretile]

Alter the bond-angle making it inactive. Other rings, maybe, but their is no example suggesting space in the mu receptor for a large ring on the beta carbon of open-chain opioids.

 

[Feretile]

https://apps.who.int/iris/bitstream/handle/10665/266102/PMC2553950.pdf?sequence=1&isAllowed=y

UNODC - Bulletin on Narcotics - 1957 Issue 4 - 005

Synthetic analgesics including substances related to pethi-dine1 have recently been comprehensively reviewed by Braenden, Eddy & Halbach (1). It is the purpose of this paper to describe important pethidine-type compounds that have been reported since this review and to present detailed...

www.unodc.org

Consider it to be an open-chain analogue of prodine. The increased number of rotatable bonds lowers affinity. The piperidine homologue was NOT active. If you take a look at secofentanyl, you will see a similar alteration and similar loss of activity.

That is not to say other analogues are not active. It's very convenient because one can simple take an amine and add it, what with it all being made in 1 step. I suspect there is a rather unusual derivative which should be about x60M and still achiral.