DXM and Morpine Chem Question

[rave23]

Hey Folks,

i have some limited knowledge in chemistry, and am not all that great. I grasp some basic concepts and have the ability to learn by reading papers, that is an advantage Please keep it 'simple' with me, even this is 'advanced'. Also i am not asking for a synthesis route or anything.

Looking at the structure of DXM and Morphine it strikes me as somewhat weird. Both molecules seem somewhat 95% identical in my eyes. How hard is it to turn DXM into Morphine? is it even possible? I don't remember reading or hearing anybody talking about such a way.
Levorphanol is also a highly similar compound, and more potent than Morphine. Since DXM is the Methyl Ester or Levorphanol it can't be that hard to do something with it to remove that ester? Judging the high availability of DXM in every country this should make a highly interesting approach of clandestine chemistry to produce a highly potent opioid from a precursor that is widely and unscheduled available?

Now forgive me if you are banging your head on your keyboard because this is like something impossible, and i am just not educated enough to recognize this. All i know is that it seems like people are cooking meth in their homes, modifying (pseudo)ephedrine slightly. Now are there ways of doing such a slight change to DXM? Not that i actually ask for a way or a recipe, i simply want to know if this is possible in a way that would make it attractive. Thanks for being understanding

 

[Ham-milton]

There's a pretty huge difference between morphine and DXM. Just looking at the bonds in the rings, you'll find a difference. Not to mention what's goin on at the bottom of the molecule (when it's pointing up...)

You can probably figure out which is which (DXM is less complicated!).

If you could alter it in such a way that the (+)-isomer is active as an opiate, probably, but AFAIK, all of the (+)-isomer's in this series are inactive as opiates.

 

[rave23]

compare DXM to this one here

Levorphanol

DXM

i don't know, my eye is not trained to spot such small but possibly important differences, that is exactly the reason why i am asking
It really doesn't look that far fetched to me. If someone could remove that O-C-H3 group and stick a O-H on there you would end up with Levorphanol wouldn't you? I am not trying to smart-ass here, because i simply have no idea if this is even possible? Are there any other differences besides that mollecule? Maybe someone who has Photoshop can Turn the mollecules and put them aside of each other?

I appreciate your response ham-milton btw.

//darn, i just see that levorphanol is kinda like a mirror image of DXM? Is that a difference? i read some stuff about stereo-chemistry and there might be a profound difference? Oh god, i probably sound so dumb right now

/// more naive idea: If there is a Dextromethorphan there has to be a Levomethorphan which should look a lot more like Levorphanol? What are the odds of "turning" Dextromethorphan around? i see this is getting more and more complicated.

 

[Ham-milton]

It's all about stereochemistry, actually (which is why I said that you'd have to find a (+)-isomer analogue that was active as an opiate). You've got a better chance of finding a hole into another world than turning a dextro into a levo.

 

[rave23]

^^^ yay okay... I wasn't familiar with the (+)-term. I just thought there would be some easy way or some other thing, but no, it shall not be

i just did some more reasearch and found that bit in the DXM-FAQ on erowid.org

These compounds would most likely have opiate activity. Unfortunately, as someone (wish I remembered who!) once put it, the isomer fairy isn't going to descend from heaven and wave her magic wand. You'd basically have to get the cross bridge to flip around (if you could do this, the hydrogens would probably conform as desired). Good luck! Personally, I don't think it can be done, at least not easily. By the time you got the lab and chemicals to do it, it'd probably be easier just to make methylfentanyl from scratch.

If you do figure out a way to do it, please don't tell anyone; nothing would bring the DEA into this faster than someone making an opiate out of DXM. You don't need to tell me either, since I don't consider opiates to be much fun. Oh, and if the isomer fairy does show up, you might as well ask her to make you some methamphetamine from Vicks Nasal InhalersTM.

 

[Ham-milton]

re: stereochemistry and methamphetamine-

I've always thought it made a lot more sense to convert L-meth into L-amph, since L-amph is a decent DA releaser, even if it has a lotmore effect peripherally.

makes more sense than eating vicks inhalers for fun, which people do!

 

[rave23]

The vics inhaler i get contain camphor and menthol and that's about it

 

[MattPsy]

Yeah, until you find a way of conjuring up stereochemistry inversion dark magic you ain't gonna be converting your DXM into levorphanol or morphine.
Pity, I know.
Converting l-methamp into l-amp doesn't sound fun. I don't know of any reactions that will cleave N-C bonds, cleanly or not. No doubt there are, though.