4 ms·

That's just impure desomorphine though

refurb 12y ago
Exactly. Desomorphine itself doesn't cause your flesh to rot off, it's the impurities in it. I think they commonly use an iodine/phosphorus reduction to remove the hydroxyl group. It doesn't surprise me that injecting a drug that has left over phosphorus triiodide or other phosphorus/iodine compounds would destroy your tissue.
girvo 12y ago
I truly don't understand how desomorphine can be created through the RP/I route. It makes pretty much zero sense based on my chemistry knowledge (BSci in Chemistry, but didn't complete it, dropped out third year). I've no idea what they're actually injecting, but I do know that a lot of the photos a number of years ago that were tagged as "Krokodil" were in fact a different drug entirely
- refurb 12y ago
  RP/I2 is basically a source of hydrogen iodide (HI). If you look at desomorphine, it's just a morphine molecule without the bottom hydroxyl group and the double bond reduced. HI will reductively deoxygenate benzyl alcohols. The oxygen removed in morphine is an allyic alcohol which is in conjugation with the aromatic ring, so it has "benzyl alcohol-like properties". HI will also reduce the double bond. As for the reaction mechanism, I'm not sure anyone has completely figured it out. One could suggest protonation of the hydroxyl group, elimination of water to form the carbocation, addition of the iodide ion(-). Another iodide ion then attacks the iodine on the molecule, which creates I2 and leaves a benzylic anion which is protonated by HI. Here is a good mechanism diagram [1]. [1]http://www.beilstein-journals.org/bjoc/content/inline/1860-5397-8-36-i1.png?scale=2.0&max-width=1024&background=FFFFFF http://www.beilstein-journals.org/bjoc/content/inline/1860-5...
  - girvo 12y ago
    I had something much larger typed up, but I'll be honest, it's been a number of years since I studied and my chemistry is a bit rusty. From what I seem to remember, I would've thought the apomorphine rearrangement would be more likely to prevail in the conditions given from a RP/I2 reaction, but I'm possibly completely off-base now (see above: rusty!). I'd be super curious to see whether anyone has properly analysed what comes out of that reaction, and what those addicts are putting into their veins (aside from horrendous toxic byproducts). The reaction method makes some sense, but reactions with opiates are typically finicky, so I've always been skeptical of these reports. I'd expect desomorphine to be present, yes, but in trace amounts at best (along with morphine and other byproducts)!

Exactly. Desomorphine itself doesn't cause your flesh to rot off, it's the impurities in it. I think they commonly use an iodine/phosphorus reduction to remove the hydroxyl group. It doesn't surprise me that injecting a drug that has left over phosphorus triiodide or other phosphorus/iodine compounds would destroy your tissue.

girvo 12y ago

I truly don't understand how desomorphine can be created through the RP/I route. It makes pretty much zero sense based on my chemistry knowledge (BSci in Chemistry, but didn't complete it, dropped out third year). I've no idea what they're actually injecting, but I do know that a lot of the photos a number of years ago that were tagged as "Krokodil" were in fact a different drug entirely

refurb 12y ago
RP/I2 is basically a source of hydrogen iodide (HI). If you look at desomorphine, it's just a morphine molecule without the bottom hydroxyl group and the double bond reduced. HI will reductively deoxygenate benzyl alcohols. The oxygen removed in morphine is an allyic alcohol which is in conjugation with the aromatic ring, so it has "benzyl alcohol-like properties". HI will also reduce the double bond. As for the reaction mechanism, I'm not sure anyone has completely figured it out. One could suggest protonation of the hydroxyl group, elimination of water to form the carbocation, addition of the iodide ion(-). Another iodide ion then attacks the iodine on the molecule, which creates I2 and leaves a benzylic anion which is protonated by HI. Here is a good mechanism diagram [1]. [1]http://www.beilstein-journals.org/bjoc/content/inline/1860-5397-8-36-i1.png?scale=2.0&max-width=1024&background=FFFFFF http://www.beilstein-journals.org/bjoc/content/inline/1860-5...
- girvo 12y ago
  I had something much larger typed up, but I'll be honest, it's been a number of years since I studied and my chemistry is a bit rusty. From what I seem to remember, I would've thought the apomorphine rearrangement would be more likely to prevail in the conditions given from a RP/I2 reaction, but I'm possibly completely off-base now (see above: rusty!). I'd be super curious to see whether anyone has properly analysed what comes out of that reaction, and what those addicts are putting into their veins (aside from horrendous toxic byproducts). The reaction method makes some sense, but reactions with opiates are typically finicky, so I've always been skeptical of these reports. I'd expect desomorphine to be present, yes, but in trace amounts at best (along with morphine and other byproducts)!