Pipermethystine is a toxic

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

present in the aerial (aboveground) portions of the

kava Kava or kava kava (''Piper methysticum'': Latin 'pepper' and Latinized Greek 'intoxicating') is a crop of the Pacific Islands. The name ''kava'' is from Tongan and Marquesan, meaning 'bitter'; other names for kava include ''ʻawa'' (Hawaiʻi), ...

plant. It is not a

kavalactone Kavalactones are a class of lactone compounds found in kava roots and Alpinia zerumbet (Shell ginger). Kavalactones are under research for potential to have various psychotropic effects, including anxiolytic and sedative/ hypnotic activities. En ...

, containing no

lactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the co ...

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 is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdrawn fro ...

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. Fiji In Fiji, kava (als ...

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% (2000ppm). Based on this retrospective study, pipermethystine is an unlikely cause for the observed hepatotoxicity of commercial Kava preparations.

References

Kava Amides Dihydropyridines Acetate esters {{pharma-stub