(R)-p-Isothiocyanatobenzoylecgonine methyl ester

(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]

(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)	Interactive image
ChemSpider	26286894^Y
PubChem CID	71308129
InChI 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^Y Key: JZGFOMFCWSMVHI-XUWVNRHRSA-N^Y 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
SMILES CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccc(cc3)N=C=S)C(=O)OC
Properties
Chemical formula	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).
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Infobox references

See also

• RTI-76, covalent binding phenyltropane
• 4'-Fluorococaine

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.