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

| ImageFile = Isothiocyanatobenzoylecgonine methyl ester.png

| IUPACName = methyl (1S,3S,4R,5R)-3-(4-isothiocyanatobenzoyl)oxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate

| OtherNames =

| Section1 = {{Chembox Identifiers

| CASNo =

| PubChem =

| 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 = 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 = JZGFOMFCWSMVHI-XUWVNRHRSA-N

| Section2 = {{Chembox Properties

| Formula = C₁₈H₂₀N₂O₄S

| MolarMass = 360.427

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| Autoignition =

'''(''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]]). ''p''-Isococ also blocks the high-affinity cocaine site in preference to the low-affinity site.<ref>Cocaine Receptor: Biochemical Characterization and Structure-Activity Relationships of Cocaine Analogues at Dopamine Transporter. F. Ivy Carroll, Anita H. Lewin, John W. Boja, and Michael J. Kuhar. Journal of Medicinal Chemistry Volume 35, Number 6</ref>

==See also==

* [[RTI-76]], covalent binding phenyltropane

==References==