Pipermethystine

Pipermethystine
Names
	IUPAC name [(3S)-6-oxo-1-(3-phenylpropanoyl)-2,3-dihydropyridin-3-yl] acetate
Identifiers
CAS Number	71627-22-0 ; 375797-98-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	9406563;
PubChem CID	11231515;
UNII	APX8C8S6AW ;
	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.

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.^[1] 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.^[2]

References

^ Nerurkar, PV; et al. (2004). "In vitro toxicity of kava alkaloid, pipermethystine, in HepG2 cells compared to kavalactones". Toxicological Sciences. 79 (1): 106–111. doi:10.1093/toxsci/kfh067. PMID 14737001.
^ Lechtenberg M, Quandt B, Schmidt M, Nahrstedt A (2008). "Is the alkaloid pipermethystine connected with the claimed liver toxicity of Kava products?". Pharmazie. 63 (1): 71–4. PMID 18271308.

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[1] Nerurkar, PV; et al. (2004). "In vitro toxicity of kava alkaloid, pipermethystine, in HepG2 cells compared to kavalactones". Toxicological Sciences. 79 (1): 106–111. doi:10.1093/toxsci/kfh067. PMID 14737001.

[2] Lechtenberg M, Quandt B, Schmidt M, Nahrstedt A (2008). "Is the alkaloid pipermethystine connected with the claimed liver toxicity of Kava products?". Pharmazie. 63 (1): 71–4. PMID 18271308.

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