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acetylated tramadol

T

toxide

Bluelighter
Joined
Mar 21, 2006
Messages
241
MY question is, I've read that tramadol is a "synthetic analog of codeine"or it's a 4phenylpiperidine analog.
Could it be acetylated/diacetylated in the usual manner to give diacetyltramadol??? Would this be worth while?
 
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It is neither an analog of codeine, nor a 4-phenylpiperidine. It has no place to acetylate it either.
 
One could convert it to an ether through, with MeI or DMS, could they not?
Interesting. Might have better BBB penetration and thus more effect, however i'm unfamilliar with opiate receptor topology so i'm unsure whether that hydroxy is needed for receptor activation.

Oh, and Wikipedia states tertiary alcohols can be oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone... would this work with that cyclohexanol hydroxy group?
Still relatively inexperienced with chem so bear with me...
 
I don't see why an acetyl group wouldn't attach itself to Tramadol's -OH. Alcohols, primary/secondary amines, and phenols can be acetylated.
 
^ Yeah, the compound with the free OH groups is the desmethylated metabolite. As this also is the main player in the mu agonism after taking the drug, I suppose it's possible; after all as an analogy, demethylated codeine is morphine, and acetylation of morphine produces heroin.
 
This maybe offtopic and maybe a stupid question but would acetylating nalbuphine create something similar to buprenorphine or something like naltrexone/naloxone
and also apomorphine which is a powefull dopamine agonist aswell as puke enhancer, it's derived from dehydration of morphine, could this be acetylated aswell to give an interesting opiate like compound???
 
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there's a thread in otherdrugs about acetylated tramadol, no conclusions were reached I guess
 
It can definately be done but more to the point by WHO? It is unlikely to be done by any professional organization. It is not going to be a big hit on the street with junkies looking for a smack high. It's unlikely to be orally very active. It's not going to be stable indefinately. And last but by no means least is that it is going to cost extra money.
 
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