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 Y
PubChem	6440936
ChemSpider	16735745 Y
Jmol-3D images	{{#if:CN3C2CCC3CC(OC(=O)/C=C/c1ccccc1)[C@@H]2C(=O)OC|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 (77 °F), 100 kPa)
Infobox references

Methylecgonine cinnamate is a natural tropane alkaloid found within the coca plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is said to be pharmacologically inactive.^[1] But some studies funded by anti-drug agencies imply that it is active when smoked.^{[citation needed]} Methylecgonine cinnamate can dimerize to the truxillic acid derivative truxilline.^[2]

See also

• Coca alkaloids
• Cocaethylene

References

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