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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.
(from tigger.uic.edu)
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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