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masturbation- Nicotine analogue

Abbott have already been here

for what it is worth Abbott synthesised these phenylpyrrolidine's and published it in 1995,

Bioorganic & Medicinal Chemistry Letters
Volume 5, Issue 9, 4 May 1995, Pages 991-996
doi:10.1016/0960-894X(95)00154-L

to briefly summarize the 1-methyl 2 phenyl pyrrolidines do bind to the nicotinic sites acetylcholine sites NAChR,

the following Ki s were observed using displacement of radiolabel cytisine,
Phenyl 450 nM
4-Bromophenyl 75 nM
3,4-Dichloro 68 nM
3,4-Methylenedioxy 46 nM

and those are the most potent. removing the N methyl reduces affinity significantly.

to put it in perspective nicotine itself has a ki somewhere in the region of 1 nM in the same assay. so unless these compounds have amazzing pharmokinetics and bioavailability they are going to be much less potent than nicotine.

Abbott no doubt have discovered a lot of interesting nicotinic agents, as they have spent a huge amount of money and time looking at the area as potential therapies for PD and alzheimers etc. some of these may have abuse potential perhaps greater than nicotine, but you can be sure these are the ones that are not researched further by abbott.
 
oh what the fuck was I thinking... I'm such a moron when I'm high. I've been bioassaying cannabinoids the past couple days, and... well, my defense is "I was high," but it's not a very good one...

What I *should* have drawn was this:

peamoronnicotinevr9.png


but that doesn't really have any connection to nicotine...

I apologise for being so retarded.
 
Cool no worries :)

I was trying to figure out where the DARI connection to the compound was coming from, had a feeling PEA might have been mixed up as did the same when I first saw the nicotine molecule.


As for nicotine analogues, non denying some unknown ones might be abusable but even if you could recreate nicotine from scratch (Assume for instance it didn't exist) - would you really want to? [I.e just for recreational effects - ignoring medical conditions like alzeimers, parkinsons etc as they lets face it are best researched by big pharm companies or academic institutions]
 
^actually the PEA you have drawn above is getting closer to carphedon.

http://en.wikipedia.org/wiki/Carphedon

still missing the C=O & alpha-methyl (and N-subst) but still possible close enough to start going in to that area. (?)

Not sure about toxicity though, would that pyrollidine be bad?
 
Yeah, as I had drawn it I doubt it'd be a dari at all. Probably nicotinic like Vector mentioned above.

I think this will have activity more like phenmetrazine than Carphedon, though. That's where I got the idea of fitting a "house ring" where they had the "other kind of stop sign-ring" (as my wife described it to me).

With the pyrrolidine rotated as it is, I don't see it having any nicotinic activity. On these phenylethyl molecules where the amine is located seems to be the most important thing. Move it further away, and you get all NE activity.

I think if you modified atomoxetine so the amine was one step closer to the phenyl ring you'd get someting with dopaminergic activity.
 
On a similar note I have also wondered what would happen if you took away the oxygen in aminorex (or 4-methyl-aminorex).

It would produce a somewhat similar type compound. (although I have a strange feeling something might not work chemically about such a molecule, someone prob knows more)
 

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Ham, your revised drawing is kinda similar to my phenmetrazine/phenethylamine idea.
 
I was just gonna post that I'd just indepenently realized that my drawing was very similar to 4-MA, which looks a lot like a 5-sided ring version of the phenmetrazine 6-sided ring... If that makes sense.

That's a cool idea, I think.
 
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