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Tropacocaine





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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

CAS Number

3D model (JSmol)
3DMet
ChEMBL
ChemSpider
ECHA InfoCard 100.007.877 Edit this at Wikidata
EC Number
  • 208-662-4
KEGG
MeSH tropacocaine

PubChem CID
  • 44279436 (1R)
  • 6942461 (1R,5R)
  • 637578 (1R,5S)
  • 6919033 (1S,5S)
    • UNII

    CompTox Dashboard (EPA)

    • 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

    Chemical formula

    		 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

    edit

    Synthesis

    edit

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

    See also

    edit

    References

    edit
    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.
  • ^ 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.
  • ^ "Cocaine analog in two steps from native plant material".


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    Last edited on 24 October 2023, at 16:56  





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