Anthopleurine: a sea anemone alarm pheromone

The sea anemone Anthopleura elegantissima responds with characteristic contraction to a pheromone released by wounded conspecifics. The alarm pheromone was isolated by ion-exchange chromatography and identified by chemical and spectroscopic methods as the quaternary ammonium ion (3-carboxy-2, 3-dihydroxy-N, N, N-trimethyl)-1-propanaminium. Median effective concentration of the crystalline pheromone is 3.5 X 10-minus 10 mole per liter of seawater.