2′-Acetoxycocaine


2′-Acetoxycocaine is a cocaine analog, with a quicker effect onset than cocaine. The acetoxy branch renders the molecule a QSAR of a 4-fold increase over cocaine in its binding potency for the dopamine transporter & a 35-fold enhanced affinity for the norepinephrine transporter. It also has a reduced selectivity for the serotonin transporter. In overall binding affinity it displaces ligands better across the board than cocaine in all monoamine categories. Salicylmethylecgonine would be an intermediate metabolite in vivo in humans 2′-Acetoxycocaine has a closer to optimum LogP for blood–brain barrier penetration this would make it a prodrug to salicylmethylecgonine due to the latter having a less efficacious LogP than its cocaine parent.
CompoundDAT
WIN 35428		5-HTT
Paroxetine		NET
Nisoxetine		Selectivity
5-HTT/DAT		Selectivity
NET/DAT		LogPɑ
Cocaine249 ± 37615 ± 1202500 ± 702.510.02.62
2′-Acetoxycocaine70 ± 1219 ± 2072 ± 93.11.02.45
2′-Hydroxycocaine
'		25 ± 4143 ± 2148 ± 25.71.92.89