[ahfei]

Why codeine not soluble in NaOH(aq) eventhough it has OH?
http://en.wikipedia.org/wiki/Codeine

And what happen to OH and amine group of morphine in acidic and alkaline solution?
http://en.wikipedia.org/wiki/Morphine

I'm new here so hi Going to be a frequent visiter here since pharmacy involve lots of chemistry

I post the link to structure pic. I believe it's just normal chemistry principle.

[AWK]

Codeine has no acidic group - it is worse soluble in NaOH than in water
The second molecule have both: acidic and basic groups

[ahfei]

emmm, still not a clear pic for me.

[AWK]

Acidic property shows phenolic OH group, codeine bears only an alcoholic OH group! MOrphine has both: phenolic and alcoholic OH groups.

[ahfei]

Thanks. AWK (what does that means?)

now i get it. Do you by chance know why morphine does not react with methylating agent like Me2SO4 without NaOH?

[AWK]

Draw the mechanism of methylation!

[lutesium]

Its not releated with the -OH group! Amines aren't soluble in basic water solutions. And nohting happens to -OH groups or somewhere else of the amines in basic or acidic solutions!!!


Lutesium...

[AWK]

Its not releated with the -OH group! Amines aren't soluble in basic water solutions. And nohting happens to -OH groups or somewhere else of the amines in basic or acidic solutions!!!


Lutesium...

phenolic OH reacts with bases! Tere is a standard test for detecting phenolic OH with such base as Na2CO3

[lutesium]

But I were talking about solubility!!! Of course phenolic -OH groups change to a -ONa+ but this change is not permenant!


Lutesium...

[AWK]

But I were talking about solubility!!! Of course phenolic -OH groups change to a -ONa+ but this change is not permenant!


Lutesium...

As far as we are talking about solubility in pure solvent , you are right.
But bases and acids react in acidic or basis conditions, respectively. Then we are talking about solubility of other compounds.

[lutesium]

The only change that I know (which is permanent) is refluxing these two substance with HI causes the rupture of the O bridge of these compounds affording Apomorphine (A D2 Dopamine agonist) as far as I know the other conditions don't effect these two amines and NO amine can dissolve in aquaeous NaOH solutions (I'm sure about this 'cuz its a fact)!!!


Lutesium...