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 mouthwatering 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.