Просмотр кода страницы Английская Википедия:(R)-p-Isothiocyanatobenzoylecgonine methyl ester

{{Английская Википедия/Панель перехода}}
{{DISPLAYTITLE:(''R'')-''p''-Isothiocyanatobenzoylecgonine methyl ester}}
{{Chembox
| verifiedrevid = 460960121
| ImageFile = P-ISOCOC.svg
| ImageSize = 
| Name = (''R'')-''p''-Isothiocyanato{{SHY}}benzoylecgonine methyl ester
| PIN = Methyl (1''R'',2''R'',3''S'',5''S'')-3-[(4-isothiocyanatobenzoyl)oxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
| OtherNames = ''p''-ISOCOC, ''p''-Isococ
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 
| PubChem = 71308129
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 26286894
| SMILES = CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccc(cc3)N=C=S)C(=O)OC
| InChI = 1/C18H20N2O4S/c1-20-13-7-8-14(20)16(18(22)23-2)15(9-13)24-17(21)11-3-5-12(6-4-11)19-10-25/h3-6,13-16H,7-9H2,1-2H3/t13-,14+,15-,16+/m0/s1
| InChIKey = JZGFOMFCWSMVHI-XUWVNRHRBQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H20N2O4S/c1-20-13-7-8-14(20)16(18(22)23-2)15(9-13)24-17(21)11-3-5-12(6-4-11)19-10-25/h3-6,13-16H,7-9H2,1-2H3/t13-,14+,15-,16+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JZGFOMFCWSMVHI-XUWVNRHRSA-N
  }}
|Section2={{Chembox Properties
| Formula = C{{sub|18}}H{{sub|20}}N{{sub|2}}O{{sub|4}}S
| MolarMass = 360.427
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility =
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt =
  }}
}}

'''<span style="word-break:break-all;">(''R'')-''p''-Isothiocyanatobenzoylecgonine methyl ester</span>''' ('''''p''-ISOCOC''') is a [[List of cocaine analogues|cocaine analogue]] and irreversible ([[covalent]]) binding inhibitor of the cocaine receptor, as well as irreversible blocker of dopamine uptake by DAT (the latter being unlike its C3 homologue [[m-ISOCOC|''m''-Isococ]]). [[Arene substitution pattern#Ortho, meta, and para substitution|''p'']]-Isococ also blocks the high-affinity cocaine site in preference to the low-affinity site.<ref>{{cite journal | vauthors = Carroll FI, Lewin AH, Boja JW, Kuhar MJ | title = Cocaine receptor: biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter | journal = Journal of Medicinal Chemistry | volume = 35 | issue = 6 | pages = 969–81 | date = March 1992 | pmid = 1552510 | doi = 10.1021/jm00084a001 }}</ref>

== See also ==
* [[List of phenyltropanes#Irreversible covalent (cf. ionic) C2 ligands|RTI-76]], covalent binding phenyltropane
* [[4'-Fluorococaine]]

== References ==
<references/>

{{stimulants}}

{{DEFAULTSORT:Isothiocyanatobenzoylecgonine methyl ester, (R)-p-}}
[[Category:Tropanes]]
[[Category:Dopamine reuptake inhibitors]]
[[Category:Stimulants]]
[[Category:Local anesthetics]]
[[Category:Methyl esters]]
[[Category:Isothiocyanates]]
[[Category:Covalent inhibitors]]


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