(R)-p-Isothiocyanatobenzoylecgonine methyl ester

Chemical compound

(R)-p-Isothiocyanatobenzoylecgonine methyl ester is a chemical compound that is structurally related to cocaine. It is a derivative of benzoylecgonine, which is the primary metabolite of cocaine. This compound is of interest in the field of medicinal chemistry and pharmacology due to its potential applications in research related to cocaine addiction and its mechanisms of action.

Chemical Structure

(R)-p-Isothiocyanatobenzoylecgonine methyl ester is characterized by the presence of an isothiocyanate group attached to the para position of the benzoyl moiety. The compound retains the core tropane structure typical of cocaine and its derivatives, which includes a bicyclic ring system.

Synthesis

The synthesis of (R)-p-Isothiocyanatobenzoylecgonine methyl ester involves the modification of benzoylecgonine. The process typically includes the introduction of an isothiocyanate group to the benzoyl ring. This modification is achieved through a series of chemical reactions that preserve the stereochemistry of the original compound.

Pharmacology

As a derivative of cocaine, (R)-p-Isothiocyanatobenzoylecgonine methyl ester is studied for its interaction with the dopamine transporter (DAT). Cocaine and its analogs are known to inhibit the reuptake of dopamine, leading to increased levels of this neurotransmitter in the synaptic cleft. This action is primarily responsible for the stimulant effects of cocaine.

Potential Applications

Research into (R)-p-Isothiocyanatobenzoylecgonine methyl ester focuses on its potential use as a tool in studying the neurobiology of cocaine addiction. By understanding how modifications to the cocaine molecule affect its interaction with the dopamine transporter, scientists aim to develop better therapeutic strategies for treating addiction.

Safety and Toxicology

As with many cocaine analogs, the safety and toxicological profile of (R)-p-Isothiocyanatobenzoylecgonine methyl ester is a subject of research. Studies typically assess its potential for abuse, toxicity, and effects on the central nervous system.

Related pages

• Cocaine
• Benzoylecgonine
• Dopamine transporter
• Neurotransmitter

Gallery

• 

  (R)-p-Isothiocyanatobenzoylecgonine methyl ester structure

•