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Natural epinephrine is (##R##)-(-)-epinephrine, and natural norepinephrine is (##R##)-(-)-norepinephrine.
The drugs, however, are often supplied as racemic mixtures.
According to theory, the chiral molecule interacts with three sites on the receptor.
The less active isomer can establish only a two-point contact.
This loss of the H-bonding interaction equals about 12 kJ/mol, and this corresponds to a 100-fold decrease in activity.
The only difference between epinephrine and norepinephrine is that the latter lacks an N-methyl group.
This does not affect the three-point connection to the receptor.
(##S##)-Norepinephrine and (##R##)-norepinephrine have the same function in the body, but the (##R##) isomer is more effective.
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