(R)-p-Isothiocyanatobenzoylecgonine methyl ester

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(R)-p-Isothiocyanatobenzoylecgonine methyl ester
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
ChemSpider 26286894 YesY
Jmol-3D images Image
Molar mass 360.427
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

(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[edit]


  1. ^ Carroll, F. I.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. (1992). "Cocaine Receptor: Biochemical Characterization and Structure-Activity Relationships of Cocaine Analogues at Dopamine Transporter". Journal of Medicinal Chemistry 35 (6): 969–981. doi:10.1021/jm00084a001. PMID 1552510.