Pipermethystine

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Pipermethystine
Names
IUPAC name
[(3S)-6-oxo-1-(3-phenylpropanoyl)-2,3-dihydropyridin-3-yl] acetate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C16H17NO4/c1-12(18)21-14-8-10-16(20)17(11-14)15(19)9-7-13-5-3-2-4-6-13/h2-6,8,10,14H,7,9,11H2,1H3/t14-/m0/s1
    Key: JLNNQCUATONMIT-AWEZNQCLSA-N
  • InChI=1/C16H17NO4/c1-12(18)21-14-8-10-16(20)17(11-14)15(19)9-7-13-5-3-2-4-6-13/h2-6,8,10,14H,7,9,11H2,1H3/t14-/m0/s1
    Key: JLNNQCUATONMIT-AWEZNQCLBW
  • O=C(N1C(=O)\C=C/[C@H](OC(=O)C)C1)CCc2ccccc2
Properties
C16H17NO4
Molar mass 287.315 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pipermethystine is a toxic alkaloid present in the aerial (aboveground) portions of the kava plant. It is not a kavalactone, containing no lactone structure. Correctly prepared kava root products will contain almost no pipermethystine.

References

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