Tropacocaine

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
CAS Number	537-26-8 ;
3D model (JSmol)	Interactive image;
3DMet	B05721;
ChEMBL	ChEMBL419588 ;
ChemSpider	10194103 ;
ECHA InfoCard	100.007.877
EC Number	208-662-4;
KEGG	C10848 ;
MeSH	tropacocaine
PubChem CID	10834; 44279436 (1R); 6942461 (1R,5R); 637578 (1R,5S); 6919033 (1S,5S);
UNII	1I92X32F6H ;
CompTox Dashboard (EPA)	DTXSID70871749 ;
	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- Key: XQJMXPAEFMWDOZ-BTTYYORXSA-N ;
	SMILES 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

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]

References

^ 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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[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.

[pmid1974643-2] 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".

[1]

[2]

[3]

Tropacocaine

Contents

Chemistry

Synthesis

See also

References

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	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	10834 44279436 (1R) 6942461 (1R,5R) 637578 (1R,5S) 6919033 (1S,5S)
UNII	1I92X32F6H^Y
CompTox Dashboard (EPA)	DTXSID70871749
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-^Y Key: XQJMXPAEFMWDOZ-BTTYYORXSA-N^Y
SMILES 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