| 词条 | Methylecgonine cinnamate |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 421098797 | ImageFile = Cinnamoylcocaine.svg | ImageSize = | IUPACName = methyl (1R,2R,3S,5S)-8-methyl-3-[(E)-3-phenylprop-2-enoyl]oxy-8- | OtherNames = Cinnamoylcocaine Cinnamylcocaine | Section1 = {{Chembox Identifiers | InChI = 1/C19H23NO4/c1-20-14-9-10-15(20)18(19(22)23-2)16(12-14)24-17(21)11-8-13-6-4-3-5-7-13/h3-8,11,14-16,18H,9-10,12H2,1-2H3/b11-8+/t14?,15?,16?,18-/m1/s1 | InChIKey = MQIXMJWNEKUAOZ-GKMMPQBVBP | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C19H23NO4/c1-20-14-9-10-15(20)18(19(22)23-2)16(12-14)24-17(21)11-8-13-6-4-3-5-7-13/h3-8,11,14-16,18H,9-10,12H2,1-2H3/b11-8+/t14?,15?,16?,18-/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = MQIXMJWNEKUAOZ-GKMMPQBVSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo = 521-67-5 | PubChem = 6440936 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID=16735745 | SMILES = CN3C2CCC3CC(OC(=O)/C=C/c1ccccc1)[C@@H]2C(=O)OC | UNII_Ref = {{fdacite|changed|FDA}} | UNII = O3I44O988U }} }}Methylecgonine cinnamate is a natural tropane alkaloid found within the coca plant.[1] Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is said to be pharmacologically inactive.[2] 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.[3] Methylecgonine cinnamate can dimerize to the truxillic acid derivative truxilline.[2] It is notable that methylecgonine cinnamate is given in patents of active cocaine analogue structures.[4][5] See also
References1. ^{{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. }} 2. ^1 Merck Chemical Index, 1985 3. ^{{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. }} 4. ^{{US patent|6479509}} Patent inventor Frank Ivy Carroll, Assignee: Research Triangle Institute 5. ^[https://patentimages.storage.googleapis.com/US6479509B1/US06479509-20021112-C00016.png U.S. patent US6479509 B1 structures given for submission, 5th compound down in image.] External links
3 : Tropane alkaloids found in Erythroxylum coca|Cinnamates|Methyl esters |
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