benzoylecgonine

Benzoylecgonine is the primary metabolite of the alkaloid cocaine, produced in the body through the action of hepatic carboxylesterase enzymes. Its chemical formula is C14H14NO4, and it possesses a benzoate ester functional group attached to the cocaine core structure. Because it lacks the potent pharmacological activity of its parent compound, benzoylecgonine is relatively inactive at neurotransmitter transporters and has negligible acute psychoactive effects.

In toxicological analysis, detection of benzoylecgonine in biological matrices such as urine, blood, or hair is the most reliable indicator of recent cocaine use. The compound is typically quantified using liquid chromatography coupled with tandem mass spectrometry or gas chromatography-mass spectrometry. The half‑life of benzoylecgonine in urine is approximately 8–12 hours, but it can be detected for days after intake, making it a valuable biomarker for forensic investigations and compliance monitoring.

Benzoylecgonine is excreted largely unchanged, although minor further metabolism can produce 6‑hydroxybenzoylecgonine and other hydroxylated derivatives. The metabolite is rarely found in significant quantities in illicit drug preparations; it appears primarily as a result of human or animal metabolism.

Regulatory treatment of benzoylecgonine varies by jurisdiction. While the compound itself is not typically listed as a controlled substance, its presence is used as evidence of cocaine consumption in legal contexts. In clinical toxicology, a positive test for benzoylecgonine usually leads to further evaluation of substance use and potential rehabilitation services.