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Tropacocaine

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

Tropacocaine
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
  • 537-26-8 Y
3D model (JSmol)
  • Interactive image
3DMet
  • B05721
ChEMBL
  • ChEMBL419588 Y
ChemSpider
  • 10194103 Y
ECHA InfoCard 100.007.877
EC Number
  • 208-662-4
KEGG
  • C10848 Y
MeSH tropacocaine
  • 10834
  • 44279436 (1R)
  • 6942461 (1R,5R)
  • 637578 (1R,5S)
  • 6919033 (1S,5S)
UNII
  • 1I92X32F6H Y
  • 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- Y
    Key: XQJMXPAEFMWDOZ-BTTYYORXSA-N Y
  • 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).

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.
  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".


tropacocaine, tropacaine, benzoylpseudotropine, pseudotropine, benzoate, descarbomethoxycocaine, cocaine, related, alkaloid, contaminant, street, cocaine, names, systematic, iupac, name, methyl, azabicyclo, octan, benzoate, other, names, benzoyloxytropane, ben. Tropacocaine tropacaine benzoylpseudotropine pseudotropine benzoate descarbomethoxycocaine is a cocaine related alkaloid 1 and a contaminant of street cocaine 2 Tropacocaine Names Systematic IUPAC name 3 exo 8 Methyl 8 azabicyclo 3 2 1 octan 3 yl benzoate Other names 3b Benzoyloxytropane Benzoylpseudotropine Pseudotropine benzoate Tropacaine Identifiers CAS Number 537 26 8 Y 3D model JSmol Interactive image 3DMet B05721 ChEMBL ChEMBL419588 Y ChemSpider 10194103 Y ECHA InfoCard 100 007 877 EC Number 208 662 4 KEGG C10848 Y MeSH tropacocaine PubChem CID 1083444279436 1R 6942461 1R 5R 637578 1R 5S 6919033 1S 5S UNII 1I92X32F6H Y InChI 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 YKey XQJMXPAEFMWDOZ BTTYYORXSA N Y SMILES CN3 C H 1CC C H 3C C H C1 OC O c2ccccc2 Properties Chemical formula C 15H 19N O 2 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 Contents 1 Chemistry 1 1 Synthesis 2 See also 3 ReferencesChemistry editSynthesis edit It can be synthesized from tropine using the Mitsunobu reaction 3 See also editHydroxytropacocaine Benzoylecgonine p Fluorotropacocaine Indatraline Tropane alkaloidReferences edit 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 nbsp This article about a heterocyclic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Tropacocaine amp oldid 1181691361, wikipedia, wiki, book, books, library,

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