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Codeinone

that doesn't sound correct sorry (drunk posting, don;'t mind me)
thebaine or it;s desmethyl deriv have no way of bonding a ion like Ca2+ .
and, the ether bridge referred to is probably the bridge in the middle of the molecule, not the 3/6-methoxy part.
O-desmethylthebainone would be 3-methoxy-morphone though. like a saturated version of hydromorphone, but at the 3 position, having a methoxy instead of a hydroxyl.
edit : Wait, desmethylthebaineone doesn;'t even make sense. Where is the methyl removed, and where is the ketone group ? it doesn't add up, the saturation in the ring system. bad name.
 
If I had to guess, I'd say that the ketone is on the 6 position, and missing the methyl on the 3. But isn't that just morphinone? I'm confused too.
 
After doing some research I've found that the substance O-desmethylthebainone is actually a side product from the conversion of morphine to hydromorphone. So the side product from the conversion of codeine to hydrocodone using the same method would be O-desmethylthebainone with a methyl group on the 3-position as far as I can tell.

I was able to find a page providing the first page of two articles describing the above conversion (here and here).

The structure of O-desmethylthebainone from the above paper is attached to this post.

Now, if the side product from the conversion of morphine is O-desmethylthebainone, and the 3-position is also called the O site (according to this page), and my understanding of "desmethyl" is correct (as far as I know it means "without methyl)... I would think the side product from the conversion of codeine (methylmorphine) would simply be thebainone.

Any thoughts?
 

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O-desmethylthebainone is not a good name, but the 4 position has a -OH on it due to the ether bridge being broken. Yes, calcium hydroxide will form an insoluable phenoxide, just like seperating morphine in opium. It would be a pain, but I guess you could remove it. Removing that bridge seems to increase potency, if anything.
 
^ Cool, so it should work... I'm not sure if they used some other naming schemes in 1949 when that article was written but that's what they called the compound. Reviewing the articles again I don't think the picture included in my post above is O-desmethylthebainone, I misunderstood the article.

But why do you say it would be a pain separating the two compounds? Wouldn't it just be a matter of basing an aqueous acidic solution of the two with, for example, calcium hydroxide and extracting with a non-polar solvent which would dissolve the hydrocodone and leave behind the O-desmethylthebainone dissolved as the calcium O-desmethylthebainoate salt?

I do wonder why they, in the article, say that the separation of the two compunds "... is effected through their different solubilities in chloroform or pyridine.". If forming the phenoxide ion indeed is effective it seems to be the easiest solution.
 
*bump*

But why do you say it would be a pain separating the two compounds? Wouldn't it just be a matter of basing an aqueous acidic solution of the two with, for example, calcium hydroxide and extracting with a non-polar solvent which would dissolve the hydrocodone and leave behind the O-desmethylthebainone dissolved as the calcium O-desmethylthebainoate salt?
Click to expand...
 
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