Structure-activity relationships of trigeminal effects for artificial and naturally occurring alkamides related to spilanthol

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Abstract

Twenty six variations of the structure of spilanthol ((E,E,Z)-2,6,8-decatrienoic acid N-isobutylamide) were synthesised starting from the appropriate unsaturated acids by amidation with simple aliphatic amines. The resulting alkamides were evaluated for their trigeminal sensory properties (burning, pungency, tingling, scratching, numbing, warming, mouth-watering, cooling). Spilanthol was the most active tingling and mouth-watering compound. trans-Pellitorine ((E,E)-2,4-decadienoic acid N-isobutylamide) showed mainly the same mouth-watering activity without the strong tingling effect. All other structural variations led to lower intensity of the trigeminal activity.

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