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Fewest carbons in an opioid?

C

clubcard

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Apr 12, 2013
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I just wondered if anyone knows which opioid has the fewest carbons? I've got one that is 13, I wondered if someone had found an example of fewer (or the same). Tapentandol has 14, just for a comparison I AFAIK you need to have an aromatic.

I found it in 'The Annual Reports in Medicinal Chemistry' volume 5.

As potent as pethidine. First discovered by the Russians then rediscovered. pethidine potency.
 
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I've got one that is 13
Click to expand...

This?

ImagesHandler.ashx
 
Close, but you need a second lone-pair which doesn't have to be and ester. Think about conformational isomerism.
 
How about sulfonamides? W-3 has only 12 carbons and it's very potent according to the study.
 
If you mean 1-phenylethyl)piperidylidene-2-(4-chlorophenyl)sulfonamide derivatives (like W18) then it has 2 benzene rings & a poperidine ring which is 17 for all of them.


... was very close. Move things about, add an oxygen and, like I said, think about conformational isomerism. It overlays 3,3-dimethyl pethidine (and before anyone asks, this has been done(.
 
Why not just post what it is? I don't think anyone is interested in a guessing game.

We already had a thread here on the simplest molecule fulfilling the morphine rule. I suspect the compound was discussed there.

Meta-Dihydrojoubertiamine is up there, and could probably be improved and simplified a bit.
 
You may have the compound following morphine rule, but not every opioid follow the rule. Also, since this one was tested, it's the lowest number KNOWN to be active. Same potency as demerol. I even gave a reference.
 
That's a paper from 1970, I wouldn't necessarily put a lot of stock in it. That said, why not post the structure? I hate to sound like a 16 year old, but this thread is a huge fail as is.

What's it doing in ADD? Sorry, NPD.
 
My favorite color is black. Just so we dont have to play guessing games anymore. :)

I agree to just post it. I dont think anyone is dying to get the answer correct.
 
Is this, by any chance, an issue with not knowing what tools to use to correctly draw the skeletal formula? If so, just post the SMILES or IUPAC and any one of us will be happy to draw it out for you and get the thread moving...

Sorry if this is an incorrect assumption, I just can't think of any other reason to ask people to discuss a compound but not fill them in on the structure of said compound... Just my observation on the matter...
 
You could draw it in paint, or use the structure drawing software on one of these websites (sigma, for instance), most have a substructure search that has a basic drawing program, you could draw it on that, use the screenshot feature, paste into paint, crop, save and post.

I don't think that's the issue though.
 
I can promise you it is real. I'm just trying to get people to think of other mu opioid agonists with 12 or less carbon, in the spirit of exploration of chemistry. I'm not dick-sizing, anyone can possess knowledge but finding solutions is intelligence and with such an amazing number of great chemists, it was a good thing, to get people sharing ideas.

I actually WANT one of the REAL chemists to match or better because it shows the ability of the people who post here.

OK MW of 191.13

That should help a lot of people. Remove the benene ring & see what's left over. You know you need an N & an O. The scaffold is similar in idea used in tapentadol tapentadol i.e. conformational isomerism is responsible for activity. It takes it's N-moiety from tilidine.

If you don't wish to play, please don't bother to answer.
 
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clubcard said:
You may have the compound following morphine rule, but not every opioid follow the rule. Also, since this one was tested, it's the lowest number KNOWN to be active. Same potency as demerol. I even gave a reference.
Click to expand...

W-3 doesn't have a phenethyl ring on piperidine's nitrogen, there's a methyl group there.
 
Just to get everything moving a bit, here is the structure of the previously discussed W-3, a 12 carbon opioid with a potency ~10x that of morphine.

SC20140522-140152.png

Sorry for the less-than-quality skeletal formula, I'm on my cell right now. Anyway, so now that this one is out there, anyone got an 11-carbon opioid? :P
 
How about 10? The thiophene analogue of W-3.

there, I win this stupid contest.

And the willingness to comb through a book from 1970 for a pointless quiz has nothing to do with intelligence and everything to do with a lack of a job.
 
Well, W3, AFAIK isn't in the patent or paper covering that class. I have a compound with an article describing activity (not just the 1970 Annual Report in Medicinal Chemistry) and Seiko has it. Hence the tread is still alive...
 
Here is something I hope everyone can appreciate:

3D QSAR for mu agonists.

http://tinypic.com/r/67tdex/8

HBA = hydrogen-bond acceptor
RA = ring aromatic
PI = positive ionizable function

I think all of the potent opioids fill all 5 of those spots.
 
Atara - interesting structure but I can find no reference from Reaxys or anywhere else. A reference would be cool. I gave may references to Seiko so I guess it's for him to decide.... looks cool though ;-)
 
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