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, c ...
of
cocaine
Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...
, formed by the liver and excreted in the urine. It is the compound tested for in most cocaine
urine drug screens and in
wastewater screenings for cocaine use.
Biochemistry and physiology
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. The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn," which ...
ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
of
ecgonine. It is a primary metabolite of cocaine, and is pharmacologically inactive. It is the corresponding
carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
of cocaine, its
methyl ester. It is formed in the
liver
The liver is a major metabolic organ (anatomy), organ exclusively found in vertebrates, which performs many essential biological Function (biology), functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of var ...
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 reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
, catalysed by
carboxylesterases, and subsequently excreted in the
urine
Urine is a liquid by-product of metabolism in humans and many other animals. In placental mammals, urine flows from the Kidney (vertebrates), kidneys through the ureters to the urinary bladder and exits the urethra through the penile meatus (mal ...
. It is readily synthesised by boiling cocaine freebase in water.
Urinalysis
Benzoylecgonine is the compound tested for in most substantive cocaine
drug urinalyses.
Presence in drinking water
Benzoylecgonine is sometimes found in drinking water supplies. In 2005, scientists found large quantities of benzoylecgonine in Italy's
Po River
The Po ( , ) is the longest river in Italy. It flows eastward across northern Italy, starting from the Cottian Alps. The river's length is , or if the Maira (river), Maira, a right bank tributary, is included. The headwaters of the Po are forme ...
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 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 (an
anticonvulsant
Anticonvulsants (also known as antiepileptic drugs, antiseizure drugs, or anti-seizure medications (ASM)) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also used in the treatme ...
) and
ibuprofen
Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used to relieve pain, fever, and inflammation. This includes dysmenorrhea, painful menstrual periods, migraines, and rheumatoid arthritis. It can be taken oral administration, ...
(a common
non-steroidal anti-inflammatory drug); the study noted that the amount of each compound present was several orders of magnitude lower than the
therapeutic dose 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.
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See also
* Coca alkaloids
* Dihydrocuscohygrine
* Hygrine
References
{{reflist
Tropane alkaloids found in Erythroxylum coca
Recreational drug metabolites
Benzoate esters
Beta-Amino acids
Human drug metabolites