Methylvanillylecgonine

Methylvanillylecgonine is a tropane alkaloid and the primary active metabolite of cocaine. It is also known as benzoylecgonine and is used in medical and forensic contexts as a diagnostic marker for cocaine use.

Chemistry

Methylvanillylecgonine is a carboxylic acid derivative of ecgonine, which is a tropane alkaloid. It is structurally similar to cocaine, but lacks the methyl ester group that is present in cocaine. This structural difference is responsible for the different pharmacological properties of methylvanillylecgonine and cocaine.

Pharmacology

Methylvanillylecgonine is a potent inhibitor of the dopamine transporter, which is responsible for the reuptake of dopamine in the synaptic cleft. By inhibiting the reuptake of dopamine, methylvanillylecgonine increases the concentration of dopamine in the synaptic cleft, leading to increased stimulation of dopamine receptors. This is thought to be the primary mechanism of action for the psychostimulant effects of cocaine.

Medical use

Methylvanillylecgonine is not used therapeutically, but it is used in medical and forensic contexts as a diagnostic marker for cocaine use. It can be detected in urine, blood, and hair samples for several days to weeks after cocaine use, depending on the frequency and amount of use.

Toxicity

The toxicity of methylvanillylecgonine is similar to that of cocaine. It can cause tachycardia, hypertension, myocardial infarction, seizures, and death in high doses. Chronic use can lead to addiction, psychosis, and other serious health problems.

See also

• Cocaine
• Ecgonine
• Dopamine transporter
• Dopamine