Tropacocaine

Tropacocaine (tropacaine, benzoylpseudotropine, pseudotropine benzoate, descarbomethoxycocaine) is a cocaine-related alkaloid[1] and a contaminant of street cocaine.[2]

Tropacocaine
Stereo Kekulé, skeletal formula of tropacocaine with some explicit hydrogens added
Names
Systematic IUPAC name
3-exo-8-Methyl-8-azabicyclo[3.2.1]octan-3-yl benzoate
Other names
3β-Benzoyloxytropane

Benzoylpseudotropine
Pseudotropine benzoate

Tropacaine
Identifiers
3D model (JSmol)
3DMet
ChEMBL
ChemSpider
ECHA InfoCard 100.007.877
EC Number
  • 208-662-4
KEGG
MeSH tropacocaine
UNII
  • InChI=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- checkY
    Key: XQJMXPAEFMWDOZ-BTTYYORXSA-N checkY
  • CN3[C@H]1CC[C@@H]3C[C@H](C1)OC(=O)c2ccccc2
Properties
C15H19NO2
Molar mass 245.322 g·mol−1
log P 2.607
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Chemistry

Synthesis

It can be synthesized from tropine using the Mitsunobu reaction.[3]

See also

References
  1. Jowett, H. A. D.; Pyman, F. L. (1909). "CXVI.?Relation between chemical constitution and physiological action in the tropeines. Part II". Journal of the Chemical Society, Transactions. 95: 1020–1032. doi:10.1039/CT9099501020.
  2. Meyer EM, Potter LT, De Vane CL, Irwin I, MacKay SL, Miller R, Ruttenber AJ (August 1990). "Effects of benzoyltropine and tropacocaine on several cholinergic processes in the rat brain". The Journal of Pharmacology and Experimental Therapeutics. 254 (2): 584–90. PMID 1974643. Retrieved 2021-01-14.
  3. "Cocaine analog in two steps from native plant material".


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