TEK - Naltrxone to oxymorphone

[vycioxas]

Naltrexone can be described as a substituted oxymorphone – here the tertiary amine methyl-substituent is replaced with methylcyclopropane. The question is, can naltrexone be made back to oxymorphone? What do you think?

[cybergenesis]

I certainly don't know the answer but having an almost unlimited supply of naltrexone tablets, it would be FANTASTIC if there was some easy way to do this.

[vycioxas]

Ye thats right, i don't think that it would be hard to do that, but my knowlege in chemistry is too short ...

[RoboCodeine7610]

I'm sure there's a way but no, it wouldn't be easy it would probably requiere a lot of chemestry knowledge and a decent lab.Good luck with it though...

[vycioxas]

Why do you think so?

[RoboCodeine7610]

Because a process as simple as converting codeine to dihydrocodeine is waaaaaay more complicated than you'd think it would be.Another example is the synthesis of oxycodone from codeine which is explained somewhere in the forum.Plus if it was as easy as mixing it with something in your kitchen, then trust me, drug chemists would be doing that all around the world.

[vycioxas]

RoboCodeine7610 heres an answer:

Methylcyclopropane provides an extreme example of the general decrease in the stability of alkyl cycloalkanes with decreasing ring size, due to the Baeyer tension. They react in a similar way to alkenes, although they don't react with the EA (cf. electrophilic addition), but with the SN2 (cf. nucleophilic substitution) reaction mechanism. These reactions are both ring opening reactions and bond cleavage reactions outside the ring. Two examples are the halogenation reactions

H3C-CycProp + HBr → H3C-CHBr-CH2-CH3 (ring opening)

H3C-CycProp + HBr → H3C-H + Br-CycProp (bond cleavage)
en.wikipedia.org/wiki/Methylcyclopropane

And here we go with alenes:
**w.chemguide.co.uk/mechanisms/freerad/alkenehbr.****

So we just need HBr. Thats all.