Nepetalactone

Nepetalactone
IUPAC name 4,7-dimethyl-5,6,7,7a-tetrahydro-cyclopenta[c]pyran-1(4aH)-one
Identifiers
CAS number	490-10-8
PubChem	161367
ChemSpider	141747 Y
Jmol-3D images	Image 1
SMILES O=C1O\C=C(/[C@H]2CC[C@@H]([C@@H]12)C)C
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 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/t6-,8+,9+/m0/s1 Key: ZDKZHVNKFOXMND-NBEYISGCBC
Properties
Molecular formula	C10H14O2
Molar mass	166.22 g mol−1
Y (verify) (what is: Y/N?) 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 from the plant catnip (Nepeta cataria), which acts as a cat attractant. Nepetalactone is bicyclic terpenoid, i.e., it is a ten-carbon compound derived from isoprene with two fused rings, a cyclopentane and a lactone. 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

4aα,7α,7aα-Nepetalactone is the active chemical in Nepeta cataria and has a characteristic effect on cats. Around 50% of cats are affected^[2]; 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^{[citation needed]}. In high doses it also has an emetic effect. Nepetalactone also has effects on some insects: it repels cockroaches and mosquitos.^{[3] [4]}

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. 
2. ^ "Catnip - Everything You Need to Know About Catnip!". http://www.cat-world.com.au/all-about-catnip. 
3. ^ Kingsley, Danny (September 3, 2001). "Catnip sends mozzies flying". ABC Science Online. http://www.abc.net.au/science/news/health/HealthRepublish_355524.htm. Retrieved February 14, 2009. 
4. ^ "Catnip and Catnip Effects". http://catnipmania.com/.