Nepetalactone

Nepetalactone

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Names
IUPAC name 4,7-Dimethyl-5,6,7,7a-tetrahydro-cyclopenta[c]pyran-1(4aH)-one
Identifiers
CAS Number	490-10-8 Y
ChemSpider	141747 Y
Jmol 3D model	Interactive image
PubChem	161367
InChI InChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3/t6-,8+,9+/m0/s1 Y Key: ZDKZHVNKFOXMND-NBEYISGCSA-N Y 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 Key: ZDKZHVNKFOXMND-NBEYISGCBC
SMILES O=C1O\C=C(/[C@H]2CC[C@@H]([C@@H]12)C)C
Properties
Chemical formula	C10H14O2
Molar mass	166.22 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Nepetalactone is an organic compound, first isolated from the plant catnip (Nepeta cataria), which acts as a cat attractant. Nepetalactone is bicyclic monoterpenoid, i.e., it is a ten-carbon compound derived from isoprene with two fused rings: a cyclopentane and a lactone. It belongs to the class of iridoids. 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.

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

4aα,7α,7aα-Nepetalactone is the active isomer in Nepeta cataria and has a characteristic effect on cats. Around 67%-80% of cats are affected. Susceptibility is gene-linked. The chemical interacts as a vapor at the olfactory epithelium.

Nepetalactone has effects on some insects: it repels cockroaches and mosquitos.