Heliopsis longipes

There was some interest in the isobutylamides derived from various plant species including affinin (Figure 3.25) from Heliopsis longipes and pipercide (Figure 3.25) from Piper nigrum. These compounds are potent voltage-dependent blockers of the sodium channel but are too unstable to be used as products directly. 

Derivation From Heliopsis longipes or made synthetically. 

N-(2 Methylpropyl)amide [25394-57-4]. Affinin. N-(2-Methylpropyl) 2,6,8 decatrienamide, 9Ci. N-Isobutyl-2,6,8-decat rienamide. Spilanthol. Alkaloid from the roots of Heliopsis longipes, Sapilanthes oleraceae and S. acmella. Powerful insecticide. Pale-yellow viscous oil. Mp23°. Bpo.5165°, Bpo.ooi 120-125°. 1 5135,... 

Heliopsis longipes (A. Gray) Blake. This plant is the source of affinin formerly believed to be derived from Erigeron affinis D.C. Affinin has m.p. 160-2°/0 3 mm. and 1-5128 and has been identified as N-iso-butyl-2 6 8-decatrienoamide. The substance is toxic to house flies at a concentratiqn of 122 8 mgm. per c.c. of solvent (Acree, Haller and Jacobsen, J. Org. Chem, 11945, 10, 236, 449. l947,12,731)., s... 

FIGURE 20 AfHiun-ielated alkamides isolated frcmi Heliopsis longipes. 

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