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  • N&PD Moderators: Skorpio

Wierd opiate

Yea but i bet the chlorine would be easier to remove than the double O of the carboxamide which is definately pretty polar. That's probably true that the confirmation is defined in some way by the Cl. I wonder if anyone would draw it without the Cl and then "kidamnesiac looking at you" hit the clean up button on chemdraw and see what the the structure does. How planar is it really by the way? I'd do it myself but don't have the program now.
Also messing with this structure with all the tertiary amines (the pyrrole and the carboxamide) might be risky as far as messing it up, and doesn't the frozen Demerol syndrome have something to do with tertiary amine rings opening up?
 
I looked into Viminol & discovered that there are some stronger derivatives. Replacing the o-Cl with a trifluoromethyl increases potency several times & replacing the pyrrolidine with a 2-pyrrolidone & the o-Cl for a p-Br and it gets quite interesting.

The most fascinating thing is that the amine substituants are really odd. The sec-butyl is the only one with decent potency & then it's sensitive to optical isomerism.

I cannot help wondering if the sec-butyl has been tried out on the 3,3 diphenyl heptaones. Since some isomers are antaginists, it may not have shown up during high-throughput screening. Could it be possible to make an ANtagonist of that class?
 
doesn't remind me that much of viminol nearly so much as BDPC and the like.
 
Well, I assume that the o-methoxy overlays the 3 position of morphine. It's basically a fentanyl type structure. I can see why you say BDPC, I think the bare -OH maps to the 14 position, but it's pretty unusual.

If you look at viminol, it's basically similar to the fentanyls. The O-Cl overlays 3, the benzyl is the epoxide, the -OH the 14 & so on.

Freaky N-substitution though. No idea why that should be optimal. Cannot help but wonder if the right isomer would make a 3,3 diaryl heptanone antagonist - something never seen before. Imagine an ORLAAM-like antagonist... could have practical uses.
 
I would think switching the N-phenethyl group with an N-allyl would probably do the trick. Usually seems to work.

I wouldn't think LAAM would be the drug I'd be looking to model anything after.
 
I'm thinking of a material to help with addiction treatment, not to get high with. I should add that there doesn't seem to be any research with optically active N substituents so it's pretty-much an unknown. The R1 isomer of viminol is x5.5 morphine but the mixture of all 6 isomers is 1/3 morphine because of the antagonist isomers.

Just an interesting N substituent...
 
For antagonist? How about N-allyl instead of N-phenethyl? (this is about the extent of my opioid SAR skills....heh)


*edit* I see Hammilton already thru that out there. But, to echo him again, I do see BDPC when I look at that structure.
 
No, when the amine has di-substitution (methadone, viminol and so on) it's a bit different. I'm not certain there are full antagonists in the fentanyl class... but I've not looked hard because of the short T1/2 - not really useful medically.
 
Alvimopan isn't an anilidopiperidine so not classed along with fentanyl derivatives. There are some 4-phenyl piperidine class antagonists that are centrally active, I think, but not very potent.
 
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