NEPETALACTON

Description

(+)-cis,trans-Nepetalactone is the primary psychoactive ingredient in catnip (Nepeta cataria). It was isolated in 1941 by S. M. McElvain and co-workers at the University of Wisconsin (Madison).?It was the first fully characterized methylcyclopentane monoterpenoid. In 2009,?M. Christmann and coauthors used?cis,trans-nepetalactone?as the starting material to synthesize (+)-englerin A, a promising kidney cancer drug candidate. The synthesis confirmed the absolute configuration of natural englerin A.

The Uses of NEPETALACTON

cis-trans-Nepetalactone, is an organic compound, isolated from the plant catnip,which acts as a cat attractant. Nepetalactone can also be effective on some insects. It repels cockroaches and mosquitos.

Definition

ChEBI: Cis-trans-nepetalactone is a cyclopentapyran that is (4aS,7aR)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by an oxo group and at positions 4 and 7 by methyl groups, respectively (the 4aS,7S,7aR-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It is an aphid sex pheromone and cat attractant, and exhibits antibacterial, antifungal, and analgesic properties. It has a role as a pheromone, a plant metabolite, an insect attractant, an analgesic, an insect repellent, an antibacterial agent and an antifungal agent. It is an iridoid monoterpenoid and a cyclopentapyran.

Production Methods

Nepetalacton can be produced 1) by isolation from American catnip oil (about 45% lactone). 2) synthetic, from Ethyl-3-methyl-2-oxocyclopentane carboxylate with Bromo butyne.