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Thought experiment: 4-tfm-amphetamine

adder said:
^ No matter, it seems it doesn't have neurotoxic effects akin to pCA, which again might point to metabolism as a factor playing role in pCA's neurotoxicity. p-Methyl in MMA can be oxidized, so it doesn't block a metabolic pathway unlike halogens and likely trifluoromethyl group. But I wonder how exactly a halogen at para position blocks oxidation of the aromatic ring? Isn't it that the oxidase produces O2(-) species that attack the ring? I've just found out the active oxygen species is a single oxygen atom, so it's the aromatic ring that attacks it, so an electron-withdrawing group should make it less efficient. But then again meta-chloroamphetamine can be oxidized at the para position, why is pCA resistant to this metabolic pathway? Is it some steric feature in P450 that makes oxidation at C3 less likely?
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I don't reckon it is this as the enzyme should be able to accomodate for quite a wide variety of substrates.

In mCA, both the chlorine and alkyl chain enhances C4 nucleophilicity.

Could an NIH shift not take place in pCA aromatic metabolism?
 
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