Benzoylecgonine is the main

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, ...

cocaine Cocaine (from , from , ultimately from Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly used recreationally for its euphoric effects. It is primarily obtained from the leaves of two Coca species native to South Am ...

, formed by the liver and excreted in the urine. It is the compound tested for in most cocaine urine drug screens.

Pharmacokinetics

Chemically, benzoylecgonine is the

benzoate Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, wh ...

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

of ecgonine. It is a primary metabolite of cocaine, and is pharmacologically inactive.

Urinalysis

Benzoylecgonine is the compound tested for in most substantive cocaine drug urinalyses. It is the corresponding

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyli ...

of cocaine, its

methyl ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are f ...

. It is formed in the

liver The liver is a major organ only found in vertebrates which performs many essential biological functions such as detoxification of the organism, and the synthesis of proteins and biochemicals necessary for digestion and growth. In humans, it i ...

by the metabolism of cocaine by

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...

, catalysed by carboxylesterases, and subsequently excreted in the

urine Urine is a liquid by-product of metabolism in humans and in many other animals. Urine flows from the kidneys through the ureters to the urinary bladder. Urination results in urine being excreted from the body through the urethra. Cellul ...

Presence in drinking water

Benzoylecgonine is sometimes found in drinking water supplies. In 2005, scientists found surprisingly large quantities of benzoylecgonine in Italy's

Po River The Po ( , ; la, Padus or ; Ancient Ligurian: or ) is the longest river in Italy. It flows eastward across northern Italy starting from the Cottian Alps. The river's length is either or , if the Maira, a right bank tributary, is included. T ...

and used its concentration to estimate the number of cocaine users in the region. In 2006, a similar study was performed in the Swiss ski town of

Saint-Moritz St. Moritz (also german: Sankt Moritz, rm, , it, San Maurizio, french: Saint-Moritz) is a high Alpine resort town in the Engadine in Switzerland, at an elevation of about above sea level. It is Upper Engadine's major town and a municipality i ...

using wastewater to estimate the daily cocaine consumption of the population. A study done in the United Kingdom found traces of benzoylecgonine in the country's drinking water supply, along with

carbamazepine Carbamazepine (CBZ), sold under the trade name Tegretol among others, is an anticonvulsant medication used primarily in the treatment of epilepsy and neuropathic pain. It is used as an adjunctive treatment in schizophrenia along with other m ...

(an

anticonvulsant Anticonvulsants (also known as antiepileptic drugs or recently as antiseizure drugs) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of ...

) and

ibuprofen Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It may also be used to close a patent ductus ar ...

(a common non-steroidal anti-inflammatory drug), although the study noted that the amount of each compound present was several orders of magnitude lower than the

therapeutic dose The therapeutic index (TI; also referred to as therapeutic ratio) is a quantitative measurement of the relative safety of a drug. It is a comparison of the amount of a therapeutic agent that causes the therapeutic effect to the amount that causes ...

and therefore did not pose a risk to the population. Preliminary studies on ecological systems show that benzoylecgonine has potential toxicity issues. Research is being conducted on degradation options such as advanced oxidation and photocatalysis for this metabolite in an effort to reduce concentrations in waste and surface waters. At environmentally relevant concentrations, benzoylecgonine has been shown to have a negative ecological impact./>

References

{{reflist Tropane alkaloids found in Erythroxylum coca Recreational drug metabolites Benzoate esters Carboxylic acids

Pharmacokinetics

Urinalysis

Presence in drinking water

See also

References