Fentanyl crisis: Nine people overdosed and died in Vancouver last night alone.
41 replies, posted
AFAIK, fentanyl is a prescription pain-killer [del]about 3x[/del] [URL="https://www.drugabuse.gov/drugs-abuse/fentanyl"]50-100x[/URL] as strong as morphine. I imagine that would make it highly addictive, too.
[QUOTE=Headhumpy;51542865]It's not made from pyridine. It's made from other starting materials which, although I haven't looked up, are probably not controlled. However, those steps do look like a pain to carry out. On the other hand, I can think of another route that avoids the use of 4-piperidone that is based on the synthesis of 4-piperidone.[/QUOTE]
Looking it up you go pyridine -> piperidine -> 4-piperidinone. Of course, that's only one route but pyridine is easy to get.
[QUOTE=download;51545798]Looking it up you go pyridine -> piperidine -> 4-piperidinone. Of course, that's only one route but pyridine is easy to get.[/QUOTE]
You can't make 4-piperidinone from piperidine.
[editline]18th December 2016[/editline]
If anything, you'd make a 4-alkoxy derivative of pyridine then reduce it to the enol ether using sodium, then hydrolyse that to get 4-piperidinone, but that's a stupid route and nowhere near worth the effort.
[QUOTE=Headhumpy;51546484]You can't make 4-piperidinone from piperidine.
[editline]18th December 2016[/editline]
If anything, you'd make a 4-alkoxy derivative of pyridine then reduce it to the enol ether using sodium, then hydrolyse that to get 4-piperidinone, but that's a stupid route and nowhere near worth the effort.[/QUOTE]
I don't claim to know much about organic chem but how hard is it to add a single nitrogen atom?
[QUOTE=download;51546505]I don't claim to know much about organic chem but how hard is it to add a single nitrogen atom?[/QUOTE]
You're not adding a single nitrogen atom when making piperidone from piperidine, you're adding an oxygen atom. To answer your question, there is nothing directing reactivity to that position, so there's no way to get the molecule to selectively react there. sp3 C-H oxidations are also difficult due to the inertness of the bond, and you can only reliably do them on simple molecules, or at benzylic or allylic positions. You usually end up with mixtures of products otherwise. See [url="https://www.scripps.edu/baran/images/grpmtgpdf/Voica_Mar_09.pdf"]this[/url] and [url="https://www2.chemistry.msu.edu/courses/cem958/10-11/talks/Zhang.pdf"]this[/url] for a quick overview on sp3 C-H oxidations.
C-H functionalisation is the holy grail of organic chemistry and if you've found a way to reliably and selectively introduce an oxygen atom at an unactivated position (no cheating using enzymes), you will immediately win a Nobel Prize. No questions asked.
[QUOTE=Headhumpy;51546525]You're not adding a single nitrogen atom when making piperidone from piperidine, you're adding an oxygen atom. To answer your question, there is nothing directing reactivity to that position, so there's no way to get the molecule to selectively react there. sp3 C-H oxidations are also difficult due to the inertness of the bond, and you can only reliably do them on simple molecules, or at benzylic or allylic positions. You usually end up with mixtures of products otherwise. See [url="https://www.scripps.edu/baran/images/grpmtgpdf/Voica_Mar_09.pdf"]this[/url] and [url="https://www2.chemistry.msu.edu/courses/cem958/10-11/talks/Zhang.pdf"]this[/url] for a quick overview on sp3 C-H oxidations.
C-H functionalisation is the holy grail of organic chemistry and if you've found a way to reliably and selectively introduce an oxygen atom at an unactivated position (no cheating using enzymes), you will immediately win a Nobel Prize. No questions asked.[/QUOTE]
Damn, that does look hard. The more you know I guess.
[QUOTE=space1;51544835]AFAIK, fentanyl is a prescription pain-killer [del]about 3x[/del] [URL="https://www.drugabuse.gov/drugs-abuse/fentanyl"]50-100x[/URL] as strong as morphine. I imagine that would make it highly addictive, too.[/QUOTE]
A drug being "strong" means little, the doses are just going to be smaller/it's going to be cut with more inert powder.
[QUOTE=Headhumpy;51546525]You're not adding a single nitrogen atom when making piperidone from piperidine, you're adding an oxygen atom. To answer your question, there is nothing directing reactivity to that position, so there's no way to get the molecule to selectively react there. sp3 C-H oxidations are also difficult due to the inertness of the bond, and you can only reliably do them on simple molecules, or at benzylic or allylic positions. You usually end up with mixtures of products otherwise. See [url="https://www.scripps.edu/baran/images/grpmtgpdf/Voica_Mar_09.pdf"]this[/url] and [url="https://www2.chemistry.msu.edu/courses/cem958/10-11/talks/Zhang.pdf"]this[/url] for a quick overview on sp3 C-H oxidations.
C-H functionalisation is the holy grail of organic chemistry and if you've found a way to reliably and selectively introduce an oxygen atom at an unactivated position (no cheating using enzymes), you will immediately win a Nobel Prize. No questions asked.[/QUOTE]
It's probably easiest to just start off with a ketone or amine and close up the ring instead of trying to hamfist it in.
Either way I don't see any obvious economical routes to do that. If you were to cladestinely produce fentanyl you'd probably need some pretty decent chemistry knowledge.
[QUOTE=Tobba;51547109]It's probably easiest to just start off with a ketone or amine and close up the ring instead of trying to hamfist it in.
Either way I don't see any obvious economical routes to do that. If you were to cladestinely produce fentanyl you'd probably need some pretty decent chemistry knowledge.[/QUOTE]
The usual route to 4-piperidone is to carry out a Dieckmann condensation on the appropriate amino diester then hydrolyse and decarboxylate in one step. The troublesome part is preparing the diester but it's doable. I could think of a route starting from other materials that would give one of the intermediates directly without having to go through 4-piperidone.
You don't really need decent chemistry knowledge, these are all reactions a first-year undergrad should know, and a serious enthusiast should be able to understand.
[QUOTE=biodude94566;51541880]That's actually really scary, at least on a personal level. My dad's had cluster headaches for over a decade and for a while he was taking Fentanyl lollipops to curb the pain. Scary shit, I was told that even licking it could kill me because of just how strong it was due to his built up resistance. I dunno how much of it was to scare me into not doing shit with them, but I stayed the fuck away from them because of it. Glad that he had a detox a few years back to get him off all the really nasty shit he was on. Now he can combat them mostly with OTC painkillers and they've got him on heart medications to keep the headaches under control. He's going to the ER/urgent care less often overall, too.[/QUOTE] Out of curiosity, how do those things taste?
[QUOTE=Maksie99;51550632]Out of curiosity, how do those things taste?[/QUOTE]
He says, "Sweet, not much flavor".
[QUOTE=biodude94566;51554548]He says, "Sweet, not much flavor".[/QUOTE]
At least that's good, I was hoping they weren't particularly tasty on the account that kids find their parents'.
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