Chem question - racemize DXM?

[MissingOxy]

Has there been any thought to a method to racemize DXM? I suspect that we'd enjoy levomethorphan better than dextro. Just a thought, and I haven't read anything about that anywhere.

[OxyContinuously]

One could consider this:

Starting from DXM, go to dextrorphan (DXM minus the methyl) Dextrorphan's opioid relative, called an isomer, is Levorphanol.

Levorphanol is a powerful opiate by itself, and levomethorphan is simply levorphanol with the methyl group attached (so you could call it a methyl ether if you wanted to)

I don't have any personal experience with levomethorphan by itself, but it has a suggested potency in the same area of hydrocodone, qualitatively, but not as strong as oxycodone, so somewhere in that middle ground.

THe only thing is that the process of going from the hydrobromide, dextromethorphan, through the appropriate steps to get to levemethorphan is kind of a pain in the ass. Yields are low, simply due to the nature of the specific reactions, and specialized equipment is a must. Things like vacuum pumps, and various solvents that are a litte hard to come by, reducing agents, and things that would generally make this project a "no-go" for anyone outside of a lab.

If only this synth were as easy as some of the methcathinone and methamphetamine recipes I have come across, which a ten year old could perform!!

Take it easy

peace

Oxy

[kingdxm]

Sorry to burst your bubble but it is impossible to get l-methorphan from d-methorphan. The chirality of the molecule is to complex to reverse isomerization. L-metho can only be made when you are trying to synthesize DXM from scratch.

[Hammilton]

yep, king's right

[robojunkie]

This racemization would be virtually impossible. Where are the functionalized sites in the morphinans with which to work? Cyanogen bromide will just lop of the N-methyl. Forget effecting a fragmentation at the quarternary center, there is nothing to activate or initiate this. Since one absolutely must somehow cleave one of the aliphatic chains at the quarternary carbon for this racemization I don't believe it is possible. The only two options, disregarding known reactivity, is to disconnect the ethyleneamine bridge at the quat carbon and reattach, or disconnect the "C" ring (the one with the allylic hydroxy in morphine) at the quat. Then one would need to racemize the other connecting point and the third (as there are 3 chiral centers here, though only 2 enantiomers and no diastereomers since they are all linked due to the annular strain). Just can't see how this could ever be done. Probably much easier to just do the 4 step synthesis used to prepare the morphinans (5 if you wanna count the facile demethylation, I suppose).

So, DM to levorphanol/levomethorphan, no dice!