This article is about the concept in chemistry.

For a discussion of enantiomers in mathematics,

see Chirality (mathematics).

(S)-(+)-lactic acid (left) and (R)-()-lactic acid (right) are nonsuperposable mirror images of
each other
In chemistry, an enantiomer (/nntimr, -, -tio-/[1] -NAN-tee--mr; from Greek
(enantos), meaning "opposite", and (mros), meaning "part"), also known as
an optical isomer, is one of two stereoisomers that are mirror images of each other that are
non-superposable (not identical), much as one's left and right hands are the same except for
being reversed along one axis (the hands cannot be made to appear identical simply by
reorientation).[2] Organic compounds that contain a chiral carbon usually have two nonsuperposable structures. These two structures are mirror images of each other and are, thus,
commonly called enantiomorphs (enantio = opposite ; morph = form), hence this structural
property is now commonly referred to as enantiomerism.
Enantiopure compounds refer to samples having, within the limits of detection, molecules of
only one chirality.[3]
When present in a symmetric environment, enantiomers have identical chemical and physical
properties except for their ability to rotate plane-polarized light (+/) by equal amounts but in
opposite directions (although the polarized light can be considered an asymmetric medium).
They are sometimes called optical isomers for this reason. A mixture of equal parts of an
optically active isomer and its enantiomer is termed racemic and has zero net rotation of
plane-polarized light because the positive rotation of each (+) form is exactly counteracted by
the negative rotation of a () one.
Enantiomer members often have different chemical reactions with other enantiomer
substances. Since many biological molecules are enantiomers, there is sometimes a marked
difference in the effects of two enantiomers on biological organisms. In drugs, for example,
often only one of a drug's enantiomers is responsible for the desired physiologic effects, while
the other enantiomer is less active, inactive, or sometimes even productive of adverse effects.
Owing to this discovery, drugs composed of only one enantiomer ("enantiopure") can be
developed to enhance the pharmacological efficacy and sometimes eliminate some side
effects. An example is eszopiclone (Lunesta), which is enantiopure and therefore administered
in doses that are exactly 1/2 of the older, racemic mixture called zopiclone. In the case of
eszopiclone, the S enantiomer is responsible for all the desired effects, while the other
enantiomer seems to be inactive. A dose of 2 mg of zopiclone must be administered to
produce the same therapeutic effect as 1 mg of eszopiclone, and that appears to be the only
difference between the two drugs.
In chemical synthesis of enantiomeric substances, non-enantiomeric precursors inevitably
produce racemic mixtures. In the absence of an effective enantiomeric environment

(precursor, chiral catalyst, or kinetic resolution), separation of a racemic mixture into its
enantiomeric components is impossible.