Tropacocaine

{{Chembox

| ImageFile = Tropacocaine.svg

| ImageClass = skin-invert-image

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageName = Stereo Kekulé, skeletal formula of tropacocaine with some explicit hydrogens added

| SystematicName= 3-exo-8-Methyl-8-azabicyclo[3.2.1]octan-3-yl benzoate

| OtherNames = 3β-Benzoyloxytropane

Benzoylpseudotropine

Pseudotropine benzoate

Tropacaine

|Section1={{Chembox Identifiers

| CASNo = 537-26-8

| CASNo_Ref = {{cascite|correct|??}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1I92X32F6H

| PubChem = 10834

| PubChem1 = 44279436

| PubChem1_Comment = (1R)

| PubChem2 = 6942461

| PubChem2_Comment = (1R,5R)

| PubChem3 = 637578

| PubChem3_Comment = (1R,5S)

| PubChem4 = 6919033

| PubChem4_Comment = (1S,5S)

| ChemSpiderID = 10194103

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 208-662-4

| KEGG = C10848

| KEGG_Ref = {{keggcite|correct|kegg}}

| MeSHName = tropacocaine

| ChEMBL = 419588

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| 3DMet = B05721

| SMILES = CN3[C@H]1CC[C@@H]3C[C@H](C1)OC(=O)c2ccccc2

| StdInChI = 1S/C15H19NO2/c1-16-12-7-8-13(16)10-14(9-12)18-15(17)11-5-3-2-4-6-11/h2-6,12-14H,7-10H2,1H3/t12-,13+,14-

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XQJMXPAEFMWDOZ-BTTYYORXSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C=15 | H=19 | N=1 | O=2

| LogP = 2.607

}}

}}

Tropacocaine (tropacaine, benzoylpseudotropine, pseudotropine benzoate, descarbomethoxycocaine) is a cocaine-related alkaloid{{Cite journal | doi = 10.1039/CT9099501020| title = CXVI.?Relation between chemical constitution and physiological action in the tropeines. Part II| journal = Journal of the Chemical Society, Transactions| volume = 95| pages = 1020–1032| year = 1909| last1 = Jowett | first1 = H. A. D. | last2 = Pyman | first2 = F. L. }} and a contaminant of street cocaine.{{cite journal

|vauthors=Meyer EM, Potter LT, De Vane CL, Irwin I, MacKay SL, Miller R, Ruttenber AJ

|title=Effects of benzoyltropine and tropacocaine on several cholinergic processes in the rat brain

|journal=The Journal of Pharmacology and Experimental Therapeutics

|volume=254

|issue=2

|pages=584–90

|date=August 1990

|pmid=1974643

|doi=

|url=https://pubmed.ncbi.nlm.nih.gov/1974643/

|accessdate=2021-01-14

}}

Chemistry

= Synthesis =

It can be synthesized from tropine using the Mitsunobu reaction.{{cite web|url=https://www.seanmichaelragan.com/html/[2008-09-10]_Cocaine_analog_in_two_steps_from_native_plant_material.shtml|title=Cocaine analog in two steps from native plant material}}

See also

References