Nepetalactone
From Wikipedia, the free encyclopedia
| Nepetalactone | |
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| IUPAC name | 4,7-dimethyl-5,6,7,7a-tetrahydrocyclo-- penta[c]pyran-1(4aH)-one |
| Identifiers | |
| CAS number | [490-10-8] |
| SMILES | C\C2=C\OC(=O)C1C2CCC1C |
| InChI | 1/C10H14O2/c1-6-3-4-8-7(2)5-12- 10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3 |
| Properties | |
| Molecular formula | C10H14O2 |
| Molar mass | 166.217 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Nepetalactone is an organic compound first isolated in the plant catnip, Nepeta cataria. The name is apparently derived from the Italian city Nepete. Nepetalactone is bicyclic terpenoid, i.e. it is a ten-carbon compound derived from isoprene with two fused rings, a cyclopentane and a cyclic ester. The structure and the effects of the compound are similar to those of valepotriates. A number of isomers of nepetalactone are known.
Nepetalactone was first reported in 1941 after it was isolated by steam distillation of catnip.[1]
[edit] Effects on animals
As 4aα,7α,7aα-nepetalactone it is the active chemical in Nepeta cataria that causes its characteristic effect on cats. Around 75% of cats are affected; susceptibility is gene-linked. The chemical interacts as a vapour at the olfactory epithelium. The compound only mildly affects humans: it is a weak sedative, antispasmodic, febrifuge, and antibacterial. In high doses it also has an emetic effect. Nepetalactone also has an effect on some insects, repelling the cockroach and mosquito[1], but it is poisonous to some common flies and a sex pheromone to aphids.
[edit] References
- ^ Samuel M. McElvain, R. D. Bright and P. R. Johnson (1941). "The Constituents of the Volatile Oil of Catnip. I. Nepetalic Acid, Nepetalactone and Related Compounds". J. Am. Chem. Soc. 63 (6): 1558-1563. doi:.
