Phenylhexylamines

[(zonk)]

Have there been any pharmacological studies regarding positional isomers of phenylhexylamines? For instance...
Since propyls seem to replace carboxylates in some cocaine like substances and beta-methylphenethylamine is orally active stimulant with some dopaminergic activity, increasing the beta-alkyl chain seems to increase the dopaminergic affinity as seen with all the benzhydryl/pipradrol compounds, maybe a butyl will be Akin to an acetate as in methylphenidate? This compound would be 2-phenylhexylamine

1-phenylhexylamine is the non ring closed analog of phencyclidine like compounds, I'm fairly sure it's been covered and don't remember it being referred to as very active however to see if my memory serves correctly I couldn't locate any info in google...

4-phenylhexylamine may also be stimulatory however now the propyl would be short an alkyl which I suppose is better than short 2 alkyls but the positioning may make it more of an opioid which I suppose to some isn't a bad thing.

3,5 and 6, would any of these be stimulatory or serotogenic or whatever???

Of course all this is speculation on my part, just wondering if there's any data out there...

 

[(zonk)]

I didn't cover n-phenyl or hexylpyridine cause I'm assuming it isn't worth it

 

[Skorpio]

I would be really surprised if any of these are serotonergic. NDRI SAR is super forgiving - it seems those transporters will play with a pretty impressive range of shapes and charges as long as it has an amine and some bulk in the right places. Think amphetamine to propylhexidrine (while propylhexidrine is certainly no ideal compound, it blows my mind that a cyclohexyl at all fits where a phenyl ring does).

SERT seems to be more selective to substitutions, where adding a carbon too much of bulk can abolish SERT activity completely.

For the phenylhexylamines, I would at vest compare them to pyrovalerones (albeit they lack the bulk on the nitrogen), which are not serotonergic. I have my doubts or even reaching that status just due to the flexibility of them without anything on the alkyls to provide rigidity through steric hinderence.

 

[Tryptamite]

I thought beta-MePhenethylamine was inactive?

 

[(zonk)]

It's active , check wiki, just had greater pressor activity in relation to amphetamine, closer to phenethylamine w maoi, but I think great beta carbons will offset that considerably