Cyclohexene-Substituted Amphetamines

[Ham-milton]

I was wondering if anyone knows if something like propylhexedrine retains it's affinity to serotonin? Would a cyclohexane substituted amphetamine analogue be better?

Obviously I'm wondering if anyone has looked at 3,4-methylenedioxypropylhexedrine as a legal MDMA replacement? It'd have way more in common with MDMA than the currently marketed replacement products with MDs stuck onto their names.

I can't imagine how much you'd need to dose, though. If MDMA : Meth dosing is like 6:1, I'd imagine that the adrenergicity of the substance would be too much to bear with the MDPH, but perhaps a cyclohexane-substitution would be a happy medium.

 

[wungchow]

the puckered structure of the cyclohexane moiety means that any substitutions won't have the same spatial placement as their phenyl counterparts. so it's hard to tell if MD-propylhexedrine will have any recreational value. also, there will be two extra stereocenters. i'm sure if you synthed all 4 stereoisomers you would hit a recreational molecule but my guess is the body load would be extreme since you'd have to take 250mg+ for a recreational dose.

 

[wungchow]

actually there will be twice as many stereoisomers, because there's an additional stereocenter at the carbon where the ethylamino sidechain is attached to the cyclohexane ring

 

[MDPVagrant]

Fwiw + IMO, "regular" propylhexedrine has a pretty significant body load at 250+ mg, but definitely provides a worthwhile mental state to accompany it.

Obviously I'm wondering if anyone has looked at 3,4-methylenedioxypropylhexedrine as a legal MDMA replacement?

An intriguing question, at least from my standpoint.