Methylecgonine cinnamate

Methylecgonine cinnamate
IUPAC name methyl (1R,2R,3S,5S)-8-methyl-3-[(E)-3-phenylprop-2-enoyl]oxy-8- azabicyclo[3.2.1]octane-2-carboxylate
Other names Cinnamoylcocaine Cinnamylcocaine
Identifiers
CAS number	521-67-5
PubChem	6440936
ChemSpider	16735745 Y
Jmol-3D images	Image 1
SMILES CN3C2CCC3CC(OC(=O)/C=C/c1ccccc1)[C@@H]2C(=O)OC
InChI InChI=1S/C19H23NO4/c1-20-14-9-10-15(20)18(19(22)23-2)16(12-14)24-17(21)11-8-13-6-4-3-5-7-13/h3-8,11,14-16,18H,9-10,12H2,1-2H3/b11-8+/t14?,15?,16?,18-/m1/s1 Y Key: MQIXMJWNEKUAOZ-GKMMPQBVSA-N Y InChI=1/C19H23NO4/c1-20-14-9-10-15(20)18(19(22)23-2)16(12-14)24-17(21)11-8-13-6-4-3-5-7-13/h3-8,11,14-16,18H,9-10,12H2,1-2H3/b11-8+/t14?,15?,16?,18-/m1/s1 Key: MQIXMJWNEKUAOZ-GKMMPQBVBP
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methylecgonine cinnamate is a natural tropane alkaloid found within the Erythroxylum coca plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is said to be pharmacologically inactive.^[1] However studies, funded by anti-drug agencies, imply that it is active when smoked. Cinnamoyl Ecgonine can dimerize to the Truxillic acid derivative: Truxilline (see Cycloaddition re Truxillic acid)^[2].

See also

• Cocaine
• Benzoylecgonine
• Truxilline
• Hydroxytropacocaine
• Tropacocaine
• Ecgonine
• Cuscohygrine
• Dihydrocuscohygrine
• Hygrine
• Cocaethylene

References

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1. ^ Merck Chemical Index, 1985
2. ^ Merck Chemical Index, 1985

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