Chemistry:Tropacocaine

From HandWiki
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
EC Number
  • 208-662-4
KEGG
MeSH tropacocaine
UNII
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

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

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. "Effects of benzoyltropine and tropacocaine on several cholinergic processes in the rat brain". The Journal of Pharmacology and Experimental Therapeutics 254 (2): 584–90. August 1990. PMID 1974643. https://pubmed.ncbi.nlm.nih.gov/1974643/. Retrieved 2021-01-14. 
  3. [2008-09-10_Cocaine_analog_in_two_steps_from_native_plant_material.shtml "Cocaine analog in two steps from native plant material"]. https://www.seanmichaelragan.com/html/[2008-09-10]_Cocaine_analog_in_two_steps_from_native_plant_material.shtml.