(R)-p-Isothiocyanatobenzoylecgonine methyl ester: Difference between revisions

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'''(''R'')-''p''-Isothiocyanatobenzoylecgonine methyl ester''' ('''''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>
'''<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 ==
== See also ==

Revision as of 09:38, 21 July 2018

(R)-p-Isothiocyanatobenzoylecgonine methyl ester
Names
IUPAC name
methyl (1S,3S,4R,5R)-3-(4-isothiocyanatobenzoyl)oxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate
Other names
p-ISOCOC, p-Isococ
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=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 checkY
    Key: JZGFOMFCWSMVHI-XUWVNRHRSA-N checkY
  • 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
    Key: JZGFOMFCWSMVHI-XUWVNRHRBQ
  • CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccc(cc3)N=C=S)C(=O)OC
Properties
C18H20N2O4S
Molar mass 360.427
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

(R)-p-Isothiocyanatobenzoylecgonine methyl ester (p-ISOCOC) is a 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). p-Isococ also blocks the high-affinity cocaine site in preference to the low-affinity site.[1]

See also

References

  1. ^ Carroll FI, Lewin AH, Boja JW, Kuhar MJ (March 1992). "Cocaine receptor: biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter". Journal of Medicinal Chemistry. 35 (6): 969–81. doi:10.1021/jm00084a001. PMID 1552510.
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