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Dxm carboxylate

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SalviaElf

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As far as I can understand if you took dxm and added 95% everclear plus acetic acid and heated it would create dxm carboxylate can anyone confirm. Also has anyone tried this compound?
 
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I can't answer if your technique would work but I do remember reading a paper on diabetes and dxm a while ago and I think they used carboxylic acid to create dxm derivatives if iirc they were less active as they didn't cross the blood brain barrier. So dxm carboxylate if it can be formed could be in the same boat as those other derivatives. Dxm is probably not the best compound and not something we discuss much on nexus.
 
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SalviaElf said:
As far as I can understand if you took dxm and added 95% everclear plus acetic acid and heated it would create dxm carboxylate can anyone confirm. Also has anyone tried this compound?
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No it wouldn't, that's bullshit chemistry thought up by a stoned idiot. Please learn some actual chemistry before attempting to prepare something that you plan to ingest.

This reaction mixture would not produce an O-acetylated derivative of anything because it is not set up properly. Even if you were by some miracle to find the correct reagents for a reaction of that type, you still would not be able to produce a DXM analogue of diamorphine since DXM lacks the requisite free hydroxy group.
 
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_Trip_ said:
By what dfz said sounds like it's not doable then.

I found the paper https://www.sciencedirect.com/scien...es,protect pancreatic islets (including human
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Thanks for the link.

We can perhaps see that the metabolite dextrorphan (DXO) would lend itself to acetylation but:
1) one would have to isolate the DXO; and/or
2) non-enzymatic preparation of DXO is also non-trivial, requiring dangerous reagents such as BBr₃ and therefore unsuitable for "kitchen chemists"; and
3) acetylation of DXO would also require at least one hard-to-obtain reagent.
4) if interpreting the OP's question more strictly, then adding a carboxy group to DXM is even less trivial and would require other dangerous and hard-to-obtain reagent. Since I suspect that the OP's intention was something other than preparing an antidiabetic agent I shan't be going into further detail here.

Probably the most important thing, chemically speaking, that one should take away from this is the difference between an acetyl [*in this example, an O acetyl] derivative and a carboxy derivative. Put simply, the former can be represented as ROCOCH₃, the latter as RCOOR'. Notice that the former has oxygen bonded to the main part of the molecule (R) whereas in the latter the bond is to carbon. Broadly put, acetylation at oxygen is somewhat easier than carbonylation of an aromatic group.

I would also suggest to look into tho properties of O-acetyldextrorphan but, as _Trip_ has pointed out, that is not the focus of this site.

PS - "DXM carboxylate" is no one specific compound hence the comment on nonsense chemistry.
 
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