BENZOYLECGONINE CAS 519-09-5

Benzoylecgonine is a major metabolite of cocaine. When cocaine is consumed, it undergoes biotransformation in the body, primarily in the liver, to form various metabolites, one of which is benzoylecgonine. This metabolite is produced through the hydrolysis of cocaine catalyzed by esterases in the liver.

The chemical structure of benzoylecgonine is derived from ecgonine, which is one of the major alkaloids found in the coca plant from which cocaine is extracted. Benzoylecgonine contains a benzoic acid group (benzoyl group) attached to the N-methyl group of ecgonine through an ester linkage. The full chemical name is methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate.

Benzoylecgonine is stable and water-soluble, which allows it to be readily excreted in urine after cocaine consumption. It is one of the major metabolites used in drug tests to detect cocaine use in individuals. Cocaine can be detected in urine for a shorter duration, but benzoylecgonine's presence can be detected for a more extended period, making it a reliable marker of cocaine use in drug screening.

Due to its prevalence in urine following cocaine consumption, benzoylecgonine is widely used as a biomarker to determine recent or chronic cocaine use in forensic toxicology, workplace drug testing, and other drug screening programs. The detection of benzoylecgonine in urine indicates that the individual has recently used cocaine, although it does not necessarily reflect the exact timing or dosage of cocaine use.

It is important to note that benzoylecgonine itself does not produce the typical euphoric effects associated with cocaine use, as it is a metabolite rather than an active drug. Instead, it serves as a marker for the presence of cocaine in the body and is a crucial tool for drug testing and monitoring cocaine use.

Benzoylecgonine itself does not have any specific uses outside the context of drug testing and forensic analysis. Its primary significance lies in being a major metabolite of cocaine, and it serves as a reliable biomarker for the recent use of cocaine.

The main use of benzoylecgonine is in drug screening and toxicology. When a person consumes cocaine, the body metabolizes it into several compounds, including benzoylecgonine. This metabolite is more stable and has a longer detection window in urine compared to cocaine itself. Therefore, urine tests for benzoylecgonine are commonly used to detect recent cocaine use and monitor drug abstinence in various settings:

1. Forensic Toxicology: Benzoylecgonine is a critical marker in forensic toxicology laboratories for identifying cocaine use in post-mortem investigations and criminal cases.

2. Workplace Drug Testing: Many employers use urine drug tests to screen for illicit drug use among employees. Benzoylecgonine testing is commonly included in these drug panels to detect cocaine use.

3. Probation and Rehabilitation Programs: Drug testing for benzoylecgonine is often used as part of probation and rehabilitation programs to monitor individuals who have a history of drug abuse.

4. Sports Doping Control: In some sports, athletes may be tested for the presence of drugs, including cocaine. Benzoylecgonine testing can be part of these anti-doping efforts.

It's important to note that benzoylecgonine itself is not a drug used for any therapeutic or recreational purpose. Its detection in biological samples is solely indicative of cocaine use. As a result, benzoylecgonine does not have any medical or industrial applications beyond its role as a metabolite in drug testing.

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