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Pipermethystine information


Pipermethystine
Names
IUPAC name
[(3S)-6-oxo-1-(3-phenylpropanoyl)-2,3-dihydropyridin-3-yl] acetate
Identifiers
CAS Number
  • 71627-22-0 checkY
  • 375797-98-1 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9406563
PubChem CID
  • 11231515
UNII
  • APX8C8S6AW checkY
InChI
  • 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
SMILES
  • O=C(N1C(=O)\C=C/[C@H](OC(=O)C)C1)CCc2ccccc2
Properties
Chemical formula
 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).
Infobox references

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.

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Bittenbender HC, Efird JT, Nerurkar PV (May 2007). "Effects of kava alkaloid, pipermethystine, and kavalactones on oxidative stress and cytochrome P450 in F-344...

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