Pipermethystine is a toxic

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

present in the aerial (aboveground) portions of the

kava Kava or kava kava (''Piper methysticum'': Latin 'pepper' and Latinized Ancient Greek, Greek 'intoxicating') is a plant in the Piperaceae, pepper family, native to the Pacific Islands. The name ''kava'' is from Tongan language, Tongan and Marqu ...

plant. It is not a

kavalactone Kavalactones are a class of lactone compounds found in kava roots and ''Alpinia zerumbet'' (shell ginger) and in several Gymnopilus, Phellinus and Inonotus fungi. Some kavalactones are bioactive. They are responsible for the psychoactive, analges ...

, containing no

lactone Lactones are cyclic carboxylic esters. They are derived from the corresponding hydroxycarboxylic acids by esterification. They can be saturated or unsaturated. Lactones are formed by lactonization, the intramolecular esterification of the corresp ...

structure. Correctly prepared kava root products will contain almost no pipermethystine.

Toxicity

Several studies suggest pipermethystine induces

hepatotoxicity Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury (DILI) is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdr ...

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 culture Kava cultures are the religious and cultural traditions of western Oceania which consume kava. There are similarities in the use of kava between the different cultures and islands, but each one also has its own traditions. Australia In Australia ...

s 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.

References

Kava Amides Dihydropyridines Acetate esters Plant toxins {{pharma-stub