2α-(Propanoyl)-3β-(2-(6-methoxynaphthyl))-tropane

2α-(Propanoyl)-3β-(2-(6-methoxynaphthyl))-tropane or WF-23 is a cocaine analogue. It is a potent dopamine reuptake inhibitor with a Ki of 5.1 nM and is around 3x more potent than cocaine as a dopamine transporter inhibitor. However, it is less potent as a serotonin transporter inhibitor, and has a significantly longer duration of action than cocaine.

Chemistry

WF-23 is a tropane derivative, which is a class of compounds that includes natural alkaloids such as cocaine and synthetic analogues like WF-23. The tropane ring system is a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. The 2α-(propanoyl)-3β-(2-(6-methoxynaphthyl)) substituents refer to the specific functional groups attached to the tropane ring in WF-23.

Pharmacology

WF-23 acts primarily as a dopamine reuptake inhibitor, meaning it blocks the reuptake of dopamine by the dopamine transporter. This leads to an increase in the extracellular concentration of dopamine, which can result in increased dopaminergic neurotransmission. This is thought to be the primary mechanism of action for the psychoactive effects of WF-23.

WF-23 is also a less potent inhibitor of the serotonin transporter, which means it can also increase the extracellular levels of serotonin. However, the role of this activity in the overall effects of WF-23 is not fully understood.

Effects

The effects of WF-23 are similar to those of other potent dopamine reuptake inhibitors, including increased alertness, euphoria, and potential for addiction. However, the longer duration of action of WF-23 compared to cocaine suggests it may have a greater potential for causing prolonged psychoactive effects and possibly a higher risk of addiction.

Legal Status

The legal status of WF-23 varies by country. In some jurisdictions, it may be considered a controlled substance due to its structural similarity to cocaine.

See Also

• Cocaine
• Dopamine reuptake inhibitor
• Serotonin reuptake inhibitor
• Tropane