Structure via PubChem · Public domain (PubChem)
pipermethystine
Sign in to savePipermethystine 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.
Chemical data
- Formula
- C16H17NO4
- Molecular weight
- 287.31 g/mol
- IUPAC name
- [(3S)-6-oxo-1-(3-phenylpropanoyl)-2,3-dihydropyridin-3-yl] acetate
- SMILES
- CC(=O)O[C@@H]1CN(C(=O)C=C1)C(=O)CCC2=CC=CC=C2
- InChIKey
- JLNNQCUATONMIT-AWEZNQCLSA-N
- XLogP
- 1.4
- Polar surface area
- 63.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- alkaloid
- Mass
- 287.115758024
Show 4 more facts
- found in taxon
- Piper longum
- canonical SMILES
- O=C(OC1C=CC(=O)N(C(=O)CCC=2C=CC=CC2)C1)C
- isomeric SMILES
- CC(=O)O[C@H]1C=CC(=O)N(C(=O)CCc2ccccc2)C1
- chemical formula
- C₁₆H₁₇NO₄
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Toxicity
- 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.
== Toxicity == Several studies suggest pipermethystine induces hepatotoxicity in humans, and was first believed to be the cause of liver failure in individuals consuming kava supplements, but not in proper root powder or fresh root, which is consumed in the traditional kava cultures of Polynesia. Later analyses of the implicated drug materials and products revealed that medical kava extracts contain less than 45 ppm of this alkaloid, while the leaves contain about 0.2% (2000 ppm). Based on this retrospective study, pipermethystine is an unlikely cause for the observed hepatotoxicity of commercial kava preparations.
Excerpted from Wikipedia’s “pipermethystine” article, available under the CC BY-SA 4.0 licence.