The Vespiary

The Hive => Chemistry Discourse => Topic started by: nowaynohow on August 26, 2003, 10:13:00 AM

Title: Naloxone aka Narcan ---> Oxymorphone ??
Post by: nowaynohow on August 26, 2003, 10:13:00 AM

If Naloxone is made from Oxymorphone, can the process be easily reveresed?  Thank You.

"Naloxone hydrochloride in structure differs from oxymorphone in that the methyl group on the nitrogen atom is replaced by an allyl group."

http://opioids.com/oxymorphone/structure.html (http://opioids.com/oxymorphone/structure.html)

http://opioids.com/naloxone/structure.html (http://opioids.com/naloxone/structure.html)

Title: I think that this is very easily be done.
Post by: slappy on August 26, 2003, 10:46:00 PM

This can very easily be done. I see this happening by quaternizing the amine with Methyl Iodide, then treatment of that salt with a Palladium⁰ species to deallylate. Careful handling will be required to achive high yields though.

In the methylation step, you would need to make the competition favor the alkylation of the amine. This is not that hard because the rate of alkylation is:

k_R3N/k_ROH @ pH7 = ~500-1000

This means keeping the raction neutral, and using <=1eq. MeI. Otherwise, you would need to protect the alcohol and phenol as the acetate esters (Ac₂O), and then saponify afterwards (K₂CO₃). The removal of the acetates might not be neccisary because that compound is probably just as active.

The quaternary salt from the previous reactiong will need to be dissolved in a solvent like DMF, and deallylated with a Palladium compound like Pd(PPh₃)₄ or Pd₂(dba)₃.

Title: Do you guys find this exciting or not?
Post by: nowaynohow on August 28, 2003, 07:25:00 AM

Could someone else please agree or disagree with what he said.  How long would this take?

Title: Reversal
Post by: morpheus on September 08, 2003, 01:17:00 AM

Are you sure its oxymorphone its made from and not
amomorphine which is like syrup of ipecac in that
it makes you puke your guts out.Amomorphine has no high
your too sick to feel it.Its used as a emetic.Swim is not always right though.