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acetylation or diacetylation of certain opioids

butane said:
With hydromorphone or oxymorphone you'd only be able to acetylate the 3 position, and that won't do anything for you. Bulky substituents on that 3 position usually decrease activity, as 3-methyl morphine (a.k.a. codeine) is much less recreational. I think the only thing you'd do by acetylating either of these two would make the come-up longer as it would have to deacetylate and also make it less potent by weight.

I don't get where people say that heroin is simply a prodrug for morphine, as that's simply not true. The effects are clearly different, and heroin is more potent by weight. If it were a prodrug, you would need an equimolar amount of each to achieve the same effect, if not more, but you actually take less heroin to get the same effect. That 6-acetyl group remains attached to the molecule as it attaches to your receptor and increases its activity in a similar manner to the 6-keto group of hydromorphone and oxymorphone.
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Yes, you can acetylate oxymorphone. the 3,14 diacetyl version is 2.5 times stronger. Placing a propanoate ester makes it 6x stronger. if you can just get a cinnamyl ester on the 14 then it's about 100x stronger.
 
220px-Dihydrocodeinone_enol_acetate.png



Thebacon or Dihydrocodeinone Enol Acetate


this stuff is slightly stonger than hydrocodone its parent , it's active on itself and also a prodrug for hydromoprhone just like hydrocodone
 
Thebacon always struck me as a dumb approved name, most people read it as
the bacon.
bacon being a highly addictive and harmful meat product best taken prepared as a sandwich.
 
Yeah I always wondered what possessed them to name an opioid after bacon!

The acetylated derivative of ketobemidone has also been reported, wonder if there is any advantage over the parent compound. Would be interesting to see O-acetyl desomorphine as well. And I wonder whether hydromorphone enol diacetate would be any better than plain acetylmorphone?
 
From a brand new paper in Bioorganic & Medicinal Chemistry Letters:
Synthesis and Pharmacological Evaluation of Hydrophobic Esters and Ethers of Butorphanol at Opioid Receptors
In Press, Accepted Manuscript, Available online 17 July 2008
Brian S. Fulton, Brian I. Knapp, Jean M. Bidlack, John L. Neumeyer

There is an inverse linear correlation between hydrophobicity (CLogP) and pKi for the ester series at the µ opioid receptor and kappa opioid receptor. Within this series, as the hydrophobicity of the compound increases the binding potency decreases. The most potent compound (4d, phenoxyacetate ester) is more hydrophobic than butorphanol by a factor of 140. Despite the loss of the 3-OH group in contributing to intermolecular noncovalent bonding as a hydrogen-bond donor, compound 4d is about two-fold more potent binding at the µ receptor and is a four-fold more potent binder at the kappa receptor than butorphanol. It would appear that the loss in hydrogen bond donor binding energy from masking of the phenol oxygen is compensated, in part, by the change in hydrophobicity by addition of a phenyl group. The logarithmic relationship of affinity and partition coefficient indicates that the binding affinity is very sensitive to the hydrophobicity of the compound. The ester series is stable to hydrolysis under the assay conditions used. The stability of 4b and 4c was studied at pH 7.4 in 25 mM phosphate buffer at 37°C by HPLC. No hydrolysis of the esters were observed after 24 hours.
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The paper also demonstrates that it is possible to selectively acylate the phenolic OH group while leaving the alkoholic OH group unaffected.

Since butorphanol is not scheduled AFAIK this might offer a simple, one-step method to turn the recreationally rather useless butorphanol into a very interesting mixed µ/kappa agonist making it possibly quite similar to oxycodone, which is also a mixed µ/kappa opioid. Unfortunately, nothing is said in the paper if the esters are agonists, partial agonists or antagonists.
 

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Mr roommate and I had been injecting 30mg morphines and we got two shot's each out of them now we have the orange 60mgs and he is trying to convince me we can still only get two shots but i don't believe him can anyone help me with this...I think we should now be able to get four shots each.
 
Ok well if you get four shot's out of a 30 wouldn't you get 8 shot's out of a 60??? And this is the thread it took me to when I typed in morphine sorry if it offended you..
 
Ah shit it was hard to understand but now that you've clarified it, 8 shots in that case. I guess I feel kinda stupid for answering it wrong before, not really because you worded it like shit. Its a pretty ridiculous question too, but I guess I applaud you for checking BL for something you were unsure of. For future reference, this would be a much more appropriate forum: http://www.bluelight.ru/vb/forumdisplay.php?forumid=16
Peace.
 
Thank you very much or your help...I know it does seem like a stupid question but am sick of arguing with him I think he was getting the extra shot's so thought I would get other opinions before I slammed him with the truth:)
 
What is or the difference?

Between oxymorphone & morphine? What is morphone
 
Morphone is the ketone of morphine (morphone = morphin-one). It has a ketone in 6-position instead of a hydroxyl.

Oxymorphone is more potent and shorter acting than morphine.

Seriously, this is nothing that you couldn't find in wikipedia.
 
mrssmiley said:
Mr roommate and I had been injecting 30mg morphines and we got two shot's each out of them now we have the orange 60mgs and he is trying to convince me we can still only get two shots but i don't believe him can anyone help me with this...I think we should now be able to get four shots each.
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I think I found the solution: Yes, you will still only get two shots each. However, his shots will now be 3x as large as yours. I think that's why he is trying so hard to convince you of his math.

On another note, someone on a different board has been claiming a theory (which I have no reason to doubt) that when acetylating morphine --> 6MAM, you will end up with codeine --> 6-MAC as well, which is supposedly lethal to humans. If that were true, wouldn't street heroin be very likely to kill, since samples often contain high levels of codeine (thus also the presumably lethal 6MAC), and they're not exactly using lab-grade extractions with their 55-gallon drums and burlap sacks in the jungle? This theory was meant as a deterrent to attempting acetylation (assuming you had AA or possibly AC, I guess) of home-baked morphine extracted from poppy tea, since unless your extraction is perfect it will have lots of codeine. Just wondering, sorry, I know it's not exactly in the spirit of the thread.
 
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socio said:
I think I found the solution: Yes, you will still only get two shots each. However, his shots will now be 3x as large as yours. I think that's why he is trying so hard to convince you of his math.

On another note, someone on a different board has been claiming a theory (which I have no reason to doubt) that when acetylating morphine --> 6MAM, you will end up with codeine --> 6-MAC as well, which is supposedly lethal to humans. If that were true, wouldn't street heroin be very likely to kill, since samples often contain high levels of codeine (thus also the presumably lethal 6MAC), and they're not exactly using lab-grade extractions with their 55-gallon drums and burlap sacks in the jungle? This theory was meant as a deterrent to attempting acetylation (assuming you had AA or possibly AC, I guess) of home-baked morphine extracted from poppy tea, since unless your extraction is perfect it will have lots of codeine. Just wondering, sorry, I know it's not exactly in the spirit of the thread.
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Assuming the morphine is pure, converting it to 6-MAM or even 3,6 DAM (heroin) will NOT create 6-MAC (monoacetylcodeine).

But yes, if extracting morphine from opium latex or CPS and the extraction is sloppy, it is very well possible to have codeine mixed in. And of course acetylating it will yield 6-MAC etc etc. This compound is VERY toxic to humans even in small amounts. Someone on another forum accidentally ingested some after acetylating morphine extracted from poppy straw and it damn nearly killed him.

However the amount of 6-MAC found in street heroin is usually minute and is below the lethal dose. Otherwise, there'd be a hell of a lot more heroin-related deaths! And most "heroin ODs" you hear about in the news is actually due to fentanyl or one of its analogs. It just 'seems' like it to LEO and it's a lot easier for them to write it off as heroin being the cause of death.
 
Acetylation of Oxymorphone

So, acetylation of morphine= Heroin.
Heroin < oxymorphone (in my opinion)
Would the acetylation of oxymorphone be possible?
 
you can diacetylate it just fine, it will acetylate as the enol ester a la thebacon. (hydrocodone enol 6'-acetate)

thank you soli, merging
 
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