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Does 3-fluoro-phenmetrazine metabolize Iinto fluorine containing metabolites ?

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T9358

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3-fluoro-phenmetrazine fluoronated metabolites??help

I have been wondering this for a while about many compounds in this case it's "3-FPM" the fluoro substituted phenmetrazine in the 3rd position on the benzene ring.

I know that its parent molecule phenmetrazine is metabolized into pseudoephedrine, ephedrine, beta hudroxy amphetamine and if there are others please enlighten me.

Out of these examples of metabolites would the 3-fluoro version have metabolites like or for example 3-fluoro-ephedrine and 3 - fluoro- beta hudroxy- amphetamine ?

I am trying to study and get knowledge about halogens and their ability to stay bonded to the metabolites
 
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The fluorine will definitely stay bonded to the benzene ring, Ar-F bond is not easy to break. Whether the fluorinated phenmetrazine derivative follows the same metabolic pathway, I don't know, but if it does, then yes you will get fluorinated metabolites. I see little reason why it wouldn't follow the same pathway.

Generally C-F bond is strong and is not metabolized. Chlorine and bromine are better leaving groups, so they may take part in some reactions, like alkylation, but fluorine is a bad one - organofluorine compounds are fairly inert. Also, normally halogens bonded to aromatic rings tend to stay there. Somebody correct me if I'm wrong.
 
I don't think 3-FPM is metabolized by ring opening. It might turn into a lactone though.

In any case the fluorine stays tightly bound to the ring and won't come off.

I suspect that people have less to worry about with 3fpm n terms of active secondary metabolites than something like amphetamine. Lord knows if you were consuming the same levels of meth as some of these forum posters go through, you'd have nothing left in your skull cavity. (I mean, when you hear about people ordering a fucking POUND of it for personal usage.... LOL)
 
I was interested to see how the structure looks rather similar to 3-fluoro-methcathinone but with the morpholine ring joining the nitrogen to the oxygen.

Subjectively, I don't feel anything like the kind of after effects that come from using ring substituted cathinones, 3-fpm left me feeling completely normal the next day, so I'm inclined to go with beligerent drunk above with the idea that the metabolites may fairly inert.
 
Ceres said:
I was interested to see how the structure looks rather similar to 3-fluoro-methcathinone but with the morpholine ring joining the nitrogen to the oxygen.

Subjectively, I don't feel anything like the kind of after effects that come from using ring substituted cathinones, 3-fpm left me feeling completely normal the next day, so I'm inclined to go with beligerent drunk above with the idea that the metabolites may fairly inert.
Click to expand...

Ring substituted cathinones are quite good serotonin releasing agents or pump inhibitors as well (e.g methylone, mephedrone). 3-FPM is releases dopamine and noradrenaline only, which I think could be the reason why you might feel normal the next day if you don't take too much.

As for metabolism, that C-F aromatic bond isn't going anywhere. Aromatic rings normally attack electrophiles rather than get attacked by nucleophiles, meaning that the fluorine atom has to give electrons to the ring when it leaves to restore aromaticity, and a fluorine cation is definitely a very poor leaving group. Even if the C-F bond is on a normal carbon chain, it is still unlikely to break as the C-F bond is strong. Also comparatively a fluorine anion isn't a great leaving group. If this was the case, you'd be more worried about your DNA getting alkylated rather than the toxicity of the fluorine which leaves. In fact that is probably why haloalkanes are toxic, because they are strong alkylating agents.
 
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You got it a bit mixed up there. ;) Leaving groups are never cations (only anions or neutral molecules), when a leaving group leaves, it leaves with a pair of electrons, it doesn't give it up. Also, in electrophilic aromatic substitution aromaticity is restored by deprotonation of a sigma complex with a base. You can have aromatic rings function as electrophiles though provided that they are electron-deficient
 
My bad, I meant that a hydrogen gives its electrons back to the ring and leaves as a proton easier than a fluorine giving its electrons back and leaving as a fluoride cation if the electrophile which the ring attacks substitutes in the place of the fluorine
 
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