Benzoylecgonine: Difference between revisions

| Watchedfields = changed

| verifiedrevid = 450846297

| IUPACName = 3β-(Benzoyloxy)tropane-2β-carboxylic acid

| SystematicName = (1''R'',2''R'',3''S'',5''S'')-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

|Section1={{Chembox Identifiers

| PubChem = 448223

| Beilstein = 89637

| EC_number = 208-263-5

|Section2={{Chembox Properties

| C=16 | H=19 | N=1 | O=4

|Section3={{Chembox Hazards

| GHSPictograms = {{GHS06}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|301}}

| PPhrases = {{P-phrases|264|270|301+310|321|330|405|501}}

| AutoignitionPt = }}

'''Benzoylecgonine''' is the main [[Cocaine#Pharmacokinetics|metabolite]] of [[cocaine]], formed by the liver and excreted in the urine. It is the compound tested for in most cocaine [[Drug test#Urine drug screen|urine drug screens]] and in [[Wastewater-based epidemiology|wastewater screenings]] for cocaine use.

==Biochemistry and physiology==

Chemically, benzoylecgonine is the [[benzoate]] [[ester]] of [[ecgonine]]. It is a primary metabolite of cocaine,<ref>{{cite journal | doi = 10.4155/fmc.11.181| pmid = 22300096| title = Accelerating cocaine metabolism as an approach to the treatment of cocaine abuse and toxicity| journal = [[Future Medicinal Chemistry]]| volume = 4| issue = 2| pages = 163–75| year = 2012| last1 = Schindler| first1 = Charles W| last2 = Goldberg| first2 = Steven R| pmc=3293209}}</ref> and is pharmacologically inactive.<ref>{{Citation|last1=Shimomura|first1=Eric T.|title=Chapter 17 - Cocaine, Crack Cocaine, and Ethanol: A Deadly Mix|date=2019-01-01|url=http://www.sciencedirect.com/science/article/pii/B9780128156070000174|work=Critical Issues in Alcohol and Drugs of Abuse Testing (Second Edition)|pages=215–224|editor-last=Dasgupta|editor-first=Amitava|publisher=Academic Press|language=en|doi=10.1016/b978-0-12-815607-0.00017-4|isbn=978-0-12-815607-0|access-date=2020-12-23|last2=Jackson|first2=George F.|last3=Paul|first3=Buddha Dev|s2cid=104375532 }}</ref> It is the corresponding [[carboxylic acid]] of cocaine, its [[methyl ester]]. It is formed in the [[liver]] by the metabolism of cocaine by [[hydrolysis]], catalysed by [[carboxylesterase]]s, and subsequently excreted in the [[urine]]. It is readily synthesised by boiling cocaine freebase in water.<ref>Findlay SP. The Three-dimensional Structure of the Cocaines. Part I. Cocaine and Pseudococaine. ''J. Am. Chem. Soc''. 1954; 76(11): 2855–2862. {{doi|10.1021/ja01640a001}}</ref>

==Urinalysis==

Benzoylecgonine is the compound tested for in most substantive cocaine [[Drug test#Urine drug screen|drug urinalyses]].

==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]] and used its concentration to estimate the number of cocaine users in the region.<ref>{{cite news|date=5 August 2005|title=Italian river 'full of cocaine'|url=http://news.bbc.co.uk/2/hi/europe/4746787.stm|newspaper=[[BBC News]]|accessdate=11 May 2014}}</ref> 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.<ref>{{cite news|date=2 February 2006|title=Tant de coke ? Stupéfiant !|url=http://www.courrierinternational.com/article/2006/02/02/tant-de-coke-stupefiant|newspaper=[[Courrier International]]|language=French|accessdate=11 May 2014}}</ref> A study done in the United Kingdom found traces of benzoylecgonine in the country's drinking water supply, along with [[carbamazepine]] (an [[anticonvulsant]]) and [[ibuprofen]] (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 index|therapeutic dose]] and therefore did not pose a risk to the population.<ref>{{cite news|last=Withnall|first=Adam|date=11 May 2014|title=Cocaine use in Britain so high it has contaminated our drinking water, report shows|url=https://www.independent.co.uk/news/uk/home-news/cocaine-use-in-britain-so-high-it-has-contaminated-our-drinking-water-report-shows-9350477.html|newspaper=[[The Independent]]|accessdate=11 May 2014}}</ref>

Preliminary studies on ecological systems show that benzoylecgonine has potential toxicity issues.<ref name=[7]>{{cite journal|last1=Binelli|first1=A.|title=First evidence of protein profile alteration due to the main cocaine metabolite (benzoylecgonine) in a freshwater model|journal=Aquatic Toxicology|date=2013|volume=140–141 |pages=268–278|pmid=23838174|last2=Marisa|first2=I|last3=Fedorova|first3=M|last4=Hoffmann|first4=R|last5=Riva|first5=C|doi=10.1016/j.aquatox.2013.06.013}}</ref> Research is being conducted on degradation options such as advanced oxidation and photocatalysis<ref name=[8]>{{cite journal|author1=Postigo, C. |author2=Sirtori, C. |author3=Oller, I. |author4=Malato, S. |author5=Maldonado, M.I. |author6=Lopez de Alda, M. |author7=Barcelo, D. |title=Solar transformation and photocatalytic treatment of cocaine in water: kinetics, characterization of major intermediate products and toxicity evaluation.|journal=Applied Catalysis B: Environmental|date=2011|volume=104|issue=1–2 |pages=37–48 |doi=10.1016/j.apcatb.2011.02.030}}</ref> 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.<ref name=[7] />

== See also ==

* [[Coca alkaloid]]s

* [[Dihydrocuscohygrine]]

* [[Hygrine]]

== References ==

[[Category:Tropane alkaloids found in Erythroxylum coca]]

[[Category:Recreational drug metabolites]]

[[Category:Benzoate esters]]

[[Category:Beta-Amino acids]]

[[Category:Human drug metabolites]]