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masturbation- Nicotine analogue

Ham-milton

Bluelighter
Joined
Jul 20, 2007
Messages
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peanicotinecg0.png


Does anyone know if this has been synthesized? For simplicity's sake I left off the hydrogen that nicotine would have had, but if that's a known compound I'd be interested as well.

I assume this would be a fair dopaminergic, but my searches have failed me.

oh, damn... I should probably draw a MD version as well. How else will I get thousands of kids across the country to eat it, and the DEA to label it "Super Ecstasy?"
 
Would the absence of the pyridine function maybe decrease the drug-receptor complex formation?

It seems like that by removing it you may be eliminating one of the key interactions (that lone pair)?

I really dont know either though.
 
I do have some real-life nicotine analog literature somewhere, in one of my ring-binders. I havent looked at that one in years but I think I can still remember that the brominated ring product was the most potent analog. I'll check on this later although I dont have it here with me today.
 
I would imagine that as drawn (the image isn't showing up for me, for you?) that it'd work more like a PEA.
 
Hamil, the image is nicotine with pyridine ring replaced with benzene ring
 
yeah, but I left off the hydrogen. I'd imagine that for a DARI, it'd only reduce activity.
 
(I know this is a chem mast thread and hence lots of (??) but..)

do you speculate it would have Dopamine reuptake effects then?

As nicotine is extremely toxic - might the benzyl group decrease or maybe increase this? If toxicity was not dependant on the pyridine (quite possibly it is but assuming is isn't just for this sentence) would that surely mean a more lipophillic toxic compound. (eek!8o )

Still wouldn't like to go anywhere near this one without lots of info. Purely from knowing nicotines extremely potent toxicity (40 - 60mg being lethal)
 
What do you mean left off the hydrogen? It still has to be there weather you draw it or not.

I've no idea about this, ill try and have a look tomorrow. What about the amphetamine analog, ie. put a CH2 between the rings?
 
The hydrogen is still there but not with the stereo bond he means.

Here's the problem: nicotine's activity is probably from the nitrogen on the benzyl ring. Look at cytosine and epibatidine. Both contain a benzyl ring modified to contain nitrogen.

Nicotine analogues sound nice tho... I'll look into this
 
How about this:

nicotineanaloguefp0.gif


The chlorine on the the methylpyrrodine group might prevent the metabolism that nicotine undergoes at that position to cotinine and the chlorine on the benzyl side of it is akin to Epibatidine.
 
I should have been more specific.

If the goal was nicotinergic (that can't be a word) activity, you'd want the pyridine ring, I'm certain.

My idea was for a cross between nicotine and amphetamine that would retain dopaminergic activity, not nicotinergic (god... wtf is the right term here, I'm pretty baked).

I would imagine that this would not retain activity at nicotine receptors.

But yeah, the structural similarity is a little worrying, though, but looking at the SARs of nicotine analogues, I think that this would be safe. I suspect much of the activity is the pyridine-structure w/ an alkyl chain.

Sorry if this doesn't make much sense. Spice Gold + the whitest pot every seen = incapacitation, and not really in a good way.
 
otb01- wouldnt that alkyl chloride be reactive in basic/neutral conditions?

Ingestion would be limited to just smoking a salt, no?

Got a link or can you explain the metabolism of nicotine for me?
 
Why not smoke it as a salt? That's how nicotine is traditionally consumed if you think about it. How about spreading it through a smokable material in an emptied out cigarette?

Here's how nicotine (primarily) metabolizes:
220px-Nicotine-2D-skeletal.png


200px-Cotinine.png


The oxygen gets double bound at the site where I have put the chlorine, hopefully making its metabolism a lot harder.
 
Ah, should probably make it something more innocuous then, CH3 maybe? Cl alpha to an amine could be easily kicked out by the lone pair on nitrogen giving an iminium ion, which would probably hydrolyse, opening the ring.
 
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