Nepetalactone is an
organic compoundAn organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
, first isolated from the
plantPlants are living organisms belonging to the kingdom Plantae. Precise definitions of the kingdom vary, but as the term is used here, plants include familiar organisms such as trees, flowers, herbs, bushes, grasses, vines, ferns, mosses, and green algae. The group is also called green plants or...
catnipNepeta is a genus of about 250 species of flowering plants in the family Lamiaceae. The members of this group are known as catnip or catmint because of their effect on cats—the nepetalactone contained in nepeta binds to the olfactory receptors of cats, typically resulting in temporary euphoria...
(
Nepeta catariaNepeta cataria is a plant in the Lamiaceae family. The common names can also be used to refer to the Nepeta genus as a whole.- Cultivation :...
), which acts as a cat attractant. Nepetalactone is bicyclic
terpenoidThe terpenoids , sometimes called isoprenoids, are a large and diverse class of naturally occurring organic chemicals similar to terpenes, derived from five-carbon isoprene units assembled and modified in thousands of ways. Most are multicyclic structures that differ from one another not only in...
, i.e., it is a ten-carbon compound derived from
isopreneIsoprene , or 2-methyl-1,3-butadiene, is a common organic compound with the formula CH2=CCH=CH2. Under standard conditions it is a colorless liquid...
with two fused rings, a
cyclopentaneCyclopentane is a highly flammable alicyclic hydrocarbon with chemical formula 510 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It occurs as a colorless liquid with a petrol-like odor. Its melting point is −94 °C...
and a
lactoneIn chemistry, a lactone is a cyclic ester which can be seen as the condensation product of an alcohol group -OH and a carboxylic acid group -COOH in the same molecule...
. The structure and the effects of the compound are similar to those of valepotriates. A number of
isomerIn chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
s of nepetalactone are known.
Nepetalactone was first reported in 1941 after it was isolated by
steam distillationSteam distillation is a special type of distillation for temperature sensitive materials like natural aromatic compounds....
of catnip.
The compound is also present in the wood of tartarian honeysuckle (
Lonicera tataricaLonicera tatarica is a species of honeysuckle known by the common name Tatarian honeysuckle. It is native to Siberia and other parts of eastern Asia, but it is probably better known in North America, where it is a widespread introduced species and noxious weed...
), 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
catThe cat , also known as the domestic cat or housecat to distinguish it from other felids and felines, is a small, usually furry, domesticated, carnivorous mammal that is valued by humans for its companionship and for its ability to hunt vermin and household pests...
s. Around 50% of cats are affected; susceptibility is
geneA gene is a molecular unit of heredity of a living organism. It is a name given to some stretches of DNA and RNA that code for a type of protein or for an RNA chain that has a function in the organism. Living beings depend on genes, as they specify all proteins and functional RNA chains...
-linked. The chemical interacts as a vapour at the
olfactory epitheliumThe olfactory epithelium is a specialized epithelial tissue inside the nasal cavity that is involved in smell. In humans, it measures about 1 square centimetre and lies on the roof of the nasal cavity about 7 cm above and behind the nostrils...
. The compound only mildly affects humans: it is a weak
sedativeA sedative or tranquilizer is a substance that induces sedation by reducing irritability or excitement....
,
antispasmodicAn antispasmodic is a drug or a herb that suppresses muscle spasms.-Smooth muscle spasm:One type of antispasmodics is used for smooth muscle contraction, especially in tubular organs of the gastrointestinal tract...
, febrifuge, and antibacterial . In high doses it also has an
emeticVomiting is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose...
effect. Nepetalactone also has effects on some insects: it repels
cockroachCockroaches are insects of the order Blattaria or Blattodea, of which about 30 species out of 4,500 total are associated with human habitations...
es and
mosquitoMosquitoes are members of a family of nematocerid flies: the Culicidae . The word Mosquito is from the Spanish and Portuguese for little fly...
s.