What Is the Chemistry of Epinephrine?


Quick Answer

Epinephrine or adrenalin is a hormone molecule formed in the adrenal glands of animals by chemical modification of the amino acid tyrosine, according to the National Center for Biotechnology Information. The chemical structure of epinephrine includes a central benzene ring substituted with two hydroxyl groups and a polymer containing an amine group of carbon, nitrogen and oxygen. The chemical formula for epinephrine is C9H13NO3, and the formal International Union of Pure and Applied Chemistry name for the compound is 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol.

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Full Answer

The synthesis of epinephrine begins with the hydroxylation of the benzene-containing amino acid tyrosine to the precursor molecule L-DOPA by tyrosine hydroxylase, writes NCBI. A second reaction produces the neurotransmitter dopamine by decarboxylation, which is converted to the final precursor noradrenaline by hydroxylation. A final methylation reaction methylates the amine group of the molecule and results in epinephrine. Once synthesized, epinephrine binds the alpha and beta adranergic receptors groups located on the cell surface of smooth muscle and other tissues to exert its biological effects. Epinephrine is degraded by catechol O-methyltransferase and monoamine oxidase B.

Industrial synthesis of ephinephrine often originates with the reaction of pyrocatechol with choloracetal chloride, reports NCBI. This is followed by reaction with methylamine and catalytic conversion of the product molecule to epinephrine. Finally separation of the desired L-epinephrine isomer is accomplished with d-tartaric acid.

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