Benzoylecgonine (
ecgonineEcgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It is has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine...
benzoate) is the primary
metaboliteMetabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. A secondary metabolite is not directly involved in those processes, but usually has...
of
cocaineCocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine. It is a stimulant of the central nervous system and an appetite suppressant...
. It is formed in the
liverThe liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...
by the metabolism of cocaine, catalysed by
carboxylesteraseIn enzymology, a carboxylesterase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are carboxylic ester and H2O, whereas its two products are alcohol and carboxylate....
s, and subsequently excreted in the
urineUrine is a liquid waste product of the body secreted by the kidneys by a process of filtration from blood called urination and excreted through the urethra. Cellular metabolism generates numerous waste compounds, many rich in nitrogen, that require elimination from the bloodstream...
. Small amounts may be traced back to certain OTC (over the counter) medications, after having been metabolized in the liver.
In 2005, scientists found surprisingly large quantities of benzoylecgonine in
ItalyItaly , officially the Italian Republic , is a country located on the Italian Peninsula in Southern Europe and on the two largest islands in the Mediterranean Sea, Sicily and Sardinia. Italy shares its northern, Alpine boundary with France, Switzerland, Austria and Slovenia...
's
Po RiverThe Po is a river that flows either or – considering the length of the Maira, a right bank tributary – eastward across northern Italy, from a spring seeping from a stony hillside at Pian del Re, a flat place at the head of the Val Po under the northwest...
and used its concentration to estimate the number of cocaine users in the region.
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Benzoylecgonine (
ecgonineEcgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It is has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine...
benzoate) is the primary
metaboliteMetabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. A secondary metabolite is not directly involved in those processes, but usually has...
of
cocaineCocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine. It is a stimulant of the central nervous system and an appetite suppressant...
. It is formed in the
liverThe liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...
by the metabolism of cocaine, catalysed by
carboxylesteraseIn enzymology, a carboxylesterase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are carboxylic ester and H2O, whereas its two products are alcohol and carboxylate....
s, and subsequently excreted in the
urineUrine is a liquid waste product of the body secreted by the kidneys by a process of filtration from blood called urination and excreted through the urethra. Cellular metabolism generates numerous waste compounds, many rich in nitrogen, that require elimination from the bloodstream...
. Small amounts may be traced back to certain OTC (over the counter) medications, after having been metabolized in the liver.
In 2005, scientists found surprisingly large quantities of benzoylecgonine in
ItalyItaly , officially the Italian Republic , is a country located on the Italian Peninsula in Southern Europe and on the two largest islands in the Mediterranean Sea, Sicily and Sardinia. Italy shares its northern, Alpine boundary with France, Switzerland, Austria and Slovenia...
's
Po RiverThe Po is a river that flows either or – considering the length of the Maira, a right bank tributary – eastward across northern Italy, from a spring seeping from a stony hillside at Pian del Re, a flat place at the head of the Val Po under the northwest...
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 waste water to estimate the daily cocaine consumption of the population.
Benzoylecgonine is used as the main pharmaceutical ingredient in the prescripition drug Esterom, a topical solution used for the relief of muscle pain.
See also
- Methylecgonine cinnamate
Methylecgonine cinnamate is a natural tropane alkaloid found within the Erythroxylum coca plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is said to be pharmacologically inactive.-See also:*Cocaine...
- Truxilline
- Hydroxytropacocaine
Hydroxytropacocaine is a tropane alkaloid found in Erythroxylum coca....
- Tropacocaine
- Ecgonine
Ecgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It is has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine...
- Cuscohygrine
Cuscohygrine is a pyrrolidine alkaloid found in coca. It can be extracted from plants of the family Solanaceae as well, including Atropa belladonna , Datura inoxia and Datura stramonium...
- Dihydrocuscohygrine
- Hygrine
Hygrine is a pyrrolidine alkaloid, found mainly in coca leaves . It was first isolated by Carl Liebermann in 1889 as an alkaloid accompanying cocaine in coca. Hygrine is extracted as a thick yellow oil, having a pungent taste and odor....