Nepetalactone

Nepetalactone
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 g·mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Nepetalactone is an organic compound first isolated in the plant catnip, Nepeta cataria. Nepetalactone is bicyclic terpenoid, i.e. it is a ten-carbon compound derived from isoprene with two fused rings, a cyclopentane and a lactone. Nepetalactone is a cat attractant. 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]

The compound is also present in the wood of tartarian honeysuckle (lonicera tatarica), shavings of which are often used in cat toys.

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 effects on some insects: it repels cockroaches and mosquitos,[1] is poisonous to some common flies and is a sex pheromone to aphids.

References

1. ^ 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:10.1021/ja01851a019.