| Revision as of 05:25, 28 March 2011 editحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits added Category:Methyl esters using HotCat← Previous edit |
Latest revision as of 03:49, 12 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix |
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{{chembox |
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{{chembox |
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| verifiedrevid = 400308101 |
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| verifiedrevid = 421098797 |
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| ImageFile = Cinnamoylcocaine.svg |
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| ImageFile = Cinnamoylcocaine.svg |
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| ImageClass = skin-invert-image |
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| ImageSize = |
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| ImageSize = 220px |
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| IUPACName = methyl (1''R'',2''R'',3''S'',5''S'')-8-methyl-3-oxy-8-<br>azabicyclooctane-2-carboxylate |
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| ImageFile2 = Methylecgonine cinnamate 3D BS.png |
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| ImageClass2 = bg-transparent |
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| ImageSize2 = 220px |
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| IUPACName = methyl (1''R'',2''R'',3''S'',5''S'')-8-methyl-3-oxy-8-<wbr>azabicyclooctane-2-carboxylate |
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| OtherNames = Cinnamoylcocaine<br>Cinnamylcocaine |
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| OtherNames = Cinnamoylcocaine<br>Cinnamylcocaine |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = MQIXMJWNEKUAOZ-GKMMPQBVSA-N |
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| StdInChIKey = MQIXMJWNEKUAOZ-GKMMPQBVSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 521-67-5 |
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| CASNo = 50763-20-7 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 521-67-5 |
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| CASNo1_Comment =(non-specific) |
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| PubChem = 6440936 |
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| PubChem = 6440936 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID=16735745 |
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| ChemSpiderID=16735745 |
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| SMILES = CN3C2CCC3CC(OC(=O)/C=C/c1ccccc1)2C(=O)OC |
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| SMILES = CN3C2CCC3CC(OC(=O)/C=C/c1ccccc1)2C(=O)OC |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = O3I44O988U |
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| Section2 = {{Chembox Properties |
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| C=19 | H=23 | N=1 | O=4 |
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'''Methylecgonine cinnamate''' is a natural ] ] found within the ] plant.<ref>{{cite journal | doi = 10.1093/oxfordjournals.aob.a086511 | title = Cocaine and Cinnamoylcocaine Content of Erythroxylum Species | journal = Annals of Botany | volume = 51 | issue = 5 | pages = 641–659 | year = 1983 | last1 = Plowman | first1 = T. | last2 = Rivier | first2 = L. }}</ref> Its more common name, '''cinnamoylcocaine''', reflects its close structural similarity to ]. It is pharmacologically inactive,<ref name=Merck>Merck Chemical Index, 1985</ref> but some studies funded by anti-drug agencies imply that it is active when smoked.{{citation needed|date=July 2013}} Furthermore, the discovery of differing impurity products yielding methylecgonine cinnamate in confiscated cocaine have led enforcing agencies to postulate that illicit manufacturers have changed their oxidation procedures when refining cocaine from a crude form.<ref>{{cite journal | pmid = 17553089 | doi=10.1111/j.1556-4029.2007.00476.x | volume=52 | issue=4 | title=Four new illicit cocaine impurities from the oxidation of crude cocaine base: formation and characterization of the diastereomeric 2,3-dihydroxy-3-phenylpropionylecgonine methyl esters from cis- and trans-cinnamoylcocaine | date=Jul 2007 | journal=J Forensic Sci | pages=860–6| last1=Casale | first1=J. F. | last2=Hays | first2=P. A. | last3=Toske | first3=S. G. | last4=Berrier | first4=A. L. | s2cid=43863333 }}</ref> Methylecgonine cinnamate can dimerize to the ] ] ].<ref name=Merck /> Methylecgonine cinnamate is mentioned in patents of active cocaine analogue structures.<ref>{{US patent|6479509}} Patent inventor Frank Ivy Carroll, Assignee: Research Triangle Institute</ref><ref></ref> |
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'''Methylecgonine cinnamate''' is a natural ] ] found within the ] plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to ]. It is said to be pharmacologically inactive.{{Fact|date=January 2008}} |
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==See also== |
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==References== |
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== References == |
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==External links== |
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* ] Microgram Vol 4 Number 14. |
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*{{cite journal | year = 2015 | title = Possibilities for discrimination between chewing of coca leaves and abuse of cocaine by hair analysis including hygrine, cuscohygrine, cinnamoylcocaine and cocaine metabolite/cocaine ratios | journal = International Journal of Legal Medicine | volume = 129 | issue = 1| pages = 69–84 | doi=10.1007/s00414-014-1061-6| pmid = 25138383 | last1 = Rubio | first1 = Nelida Cristina | last2 = Hastedt | first2 = Martin | last3 = Gonzalez | first3 = Jorge | last4 = Pragst | first4 = Fritz | s2cid = 20712368 }} |
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