Nepetalactone
Overview
 
Nepetalactone is an organic compound
Organic compound
An 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 plant
Plant
Plants 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...

 catnip
Nepeta
Nepeta 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 cataria
Nepeta cataria
Nepeta 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 terpenoid
Terpenoid
The 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 isoprene
Isoprene
Isoprene , 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 cyclopentane
Cyclopentane
Cyclopentane 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 lactone
Lactone
In 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 isomer
Isomer
In 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 distillation
Steam distillation
Steam 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 tatarica
Lonicera tatarica
Lonicera 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.
4aα,7α,7aα-Nepetalactone is the active chemical in Nepeta cataria and has a characteristic effect on cat
Cat
The 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.
 
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