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. 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).

See also

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