| Revision as of 18:29, 16 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChEMBL_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit |
Latest revision as of 16:36, 28 April 2024 edit undo173.23.104.189 (talk)No edit summary |
| (63 intermediate revisions by 44 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 450604403 |
|
| verifiedrevid = 450846297 |
|
| ImageFile = Benzoylecgonine-2D-skeletal.png |
|
| ImageFile = Benzoylecgonine-2D-skeletal.png |
|
| ImageSize = |
|
| ImageSize = |
|
| ImageFile1 = Benzoylecgonine-3D-balls.png |
|
| ImageFile1 = Benzoylecgonine-3D-balls.png |
|
| ImageSize1 = |
|
| ImageSize1 = |
|
| IUPACName = 3-Benzoyloxy-8-methyl-8-azabicyclooctane-4-carboxylic acid |
|
| IUPACName = 3β-(Benzoyloxy)tropane-2β-carboxylic acid |
|
|
| SystematicName = (1''R'',2''R'',3''S'',5''S'')-3-(Benzoyloxy)-8-methyl-8-azabicyclooctane-2-carboxylic acid |
|
| OtherNames = |
|
| OtherNames = |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 395095 |
|
| ChemSpiderID = 395095 |
| Line 20: |
Line 22: |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo = 519-09-5 |
|
| CASNo = 519-09-5 |
|
| PubChem = |
|
| PubChem = 448223 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank = DB01515 |
|
| DrugBank = DB01515 |
| Line 27: |
Line 29: |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = C10847 |
|
| KEGG = C10847 |
|
|
| Beilstein = 89637 |
|
|
| EC_number = 208-263-5 |
|
| SMILES = CN12CC1((C2)OC(=O)c3ccccc3)C(=O)O |
|
| SMILES = CN12CC1((C2)OC(=O)c3ccccc3)C(=O)O |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C=16|H=19|N=1|O=4 |
|
| C=16 | H=19 | N=1 | O=4 |
|
| Appearance = |
|
| Appearance = |
|
| Density = |
|
| Density = |
| Line 36: |
Line 40: |
|
| BoilingPt = |
|
| BoilingPt = |
|
| Solubility = }} |
|
| Solubility = }} |
|
| Section3 = {{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
| MainHazards = |
|
| MainHazards = |
|
|
| GHSPictograms = {{GHS06}} |
|
|
| GHSSignalWord = Danger |
|
|
| HPhrases = {{H-phrases|301}} |
|
|
| PPhrases = {{P-phrases|264|270|301+310|321|330|405|501}} |
|
| FlashPt = |
|
| FlashPt = |
|
| Autoignition = }} |
|
| AutoignitionPt = }} |
|
}} |
|
}} |
|
|
'''Benzoylecgonine''' is the main ] of ], formed by the liver and excreted in the urine. It is the compound tested for in most cocaine ] and in ] for cocaine use. |
|
|
|
|
|
|
==Biochemistry and physiology== |
|
'''Benzoylecgonine''' is a ] ] and the main ] of ]. |
|
|
|
Chemically, benzoylecgonine is the ] ] of ]. 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 = ]| 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 ] of cocaine, its ]. It is formed in the ] by the metabolism of cocaine by ], catalysed by ]s, and subsequently excreted in the ]. 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> |
|
|
|
|
|
==History== |
|
==Urinalysis== |
|
|
Benzoylecgonine is the compound tested for in most substantive cocaine ]. |
|
Benzoylecgonine is used as the main pharmaceutical ingredient in the prescription drug '''Esterom''', a topical solution used for the relief of muscle pain. |
|
|
|
|
|
|
|
==Presence in drinking water== |
|
==Pharmacokinetics== |
|
|
|
Benzoylecgonine is sometimes found in drinking water supplies. In 2005, scientists found surprisingly large quantities of benzoylecgonine in Italy's ] 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=]|accessdate=11 May 2014}}</ref> In 2006, a similar study was performed in the Swiss ski town of ] 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=]|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 ] (an ]) and ] (a common ]), although the study noted that the amount of each compound present was several orders of magnitude lower than the ] 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=]|accessdate=11 May 2014}}</ref> |
|
Chemically, benzoylecgonine is ] ]. It is the primary metabolite of cocaine. |
|
|
|
|
|
|
|
Preliminary studies on ecological systems show that benzoylecgonine has potential toxicity issues.<ref name=>{{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=>{{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= /> |
|
==Urinalysis== |
|
|
Benzoylecgonine is the compound tested for in most substantive cocaine ]. It is the corresponding ] resulting of the hydrolysis of the ] of cocaine. It is formed in the ] by the metabolism of cocaine, catalysed by ]s, and subsequently excreted in the ]. It can be found in the urine for considerably longer than the cocaine itself which is generally cleared out within 5 days. Small amounts may be traced back to certain OTC (over the counter) medications, after having been metabolized in the liver.{{Citation needed|date=March 2008}} |
|
|
|
|
|
|
|
== See also == |
|
In 2005, scientists found surprisingly large quantities of benzoylecgonine in ]'s ] and used its concentration to estimate the number of cocaine users in the region.<ref>, BBC News, 5 August 2005</ref> In 2006, a similar study was performed in the Swiss ski town of ] using waste water to estimate the daily cocaine consumption of the population.<ref> (French), Courrier International</ref> |
|
|
|
* ]s |
|
⚫ |
* ] |
|
⚫ |
* ] |
|
|
|
|
|
==See also== |
|
== References == |
|
*] |
|
|
*] |
|
|
*] |
|
|
*] |
|
|
*] |
|
|
*] |
|
| ⚫ |
*] |
|
| ⚫ |
*] |
|
|
|
|
|
==References== |
|
|
{{reflist}} |
|
{{reflist}} |
|
|
|
|
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
|
] |
|
|
|
|
|
] |
|
|
|
|
{{analgesic-stub}} |
|
|
|
|
|
] |
|
|
] |
|
|
] |
|