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alpha-allylphenethylamine

I

ingo_1978

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May 20, 2006
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Does anyone know if this would have any activity or is the chain too long at the alpha postion?

I suppose there is beta-allylphenethylamine, N-allylphenethylamine and alpha-allyl,N-allylphenethylamine too. These seem quite easily obtainable too.
 
1,2 diphenylethanamine and its piperidine cousin are NMDA channel blockers, IIRC.

alpha-ethyl phenethylamine is much less active than amphetamine, alpha-allyl won't be much better. why not alpha-fluoromethyl amphetamine?
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I'm just considering possible stimulants which fall outside the UK phenethylamine act, hence no substitued alkyls. I think the non-methylated 1,2-diphenylethanamine version of lefetamine would not be NMDA anatagonist but may be wrong?
 
It does so in other compounds positioned adjacent to electronegative groups that may be involved in metabolism, the prime example is methoxyflurane. Alkylhalides are not generally known for their metabolic inertness (actually, they tend to alkylate things in vitro and in vivo). Not sure if this would happen with MAO, but I'd be hesitant to ingest that one. Even if you have binding but not general metabolism of the compound to enzymes, anything causing rearrangement of the hydrogen could cause the fluorine to pop off.
 
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I'm thinking the fluorine on the alpha carbon of amphetamine is further from the amine than the fluorines on methoxyflurane - and even then it's fluorine instead of heavier halides which are leaving groups. AFAICT, stuff like AM-2201 and p-fluoroamphetamine don't lose their fluorines to metabolism or act as alkylating agents the same way alkyl chlorides/bromides/iodides do. Ethers can be metabolically cleaved to alcohols, generating a pathway for the fluorines to be cleaves along the route to a carboxylic acid, but I don't think that the alpha methyl is touched to such an extent in amphetamine metabolism.

2-fluoro nitroethane would be fucking nasty to work with though, I feel sorry for anyone manufacturing alpha-fluoromethyl-phetamine.
 
I don't think you can draw meaningful conclusions from p-FA to apply to a-fluoromethyl-PEA.

At the other site we were talking about beta-fluoro and beta-difluoro-amphetamines and methamphetamines as alternatives. Concern about aziridine being formed as a contaminant (as with the HI-Meth Route) seemed to be dismissed for fluoro, but none of the other halogens, certain not the difluoro. Don't see any obvious reason why that wouldn't be a decent stimulant, though probably at least as toxic as methamphetamine
 
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