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Adrenaline (adrenaline or epinephrine)

Time: [2019-01-28]

Adrenaline (adrenaline or epinephrine), mainly used for the treatment of cardiac arrest, bronchial asthma, anaphylactic shock, but also for the treatment of urticaria, hay fever and nasal mucosa or gum bleeding.

There is a chiral center in the adrenaline molecule, so there are two enantiomers, R-adrenalin and S-adrenalin, and R-adrenalin, which is mainly physiologically active.

At present, adrenaline synthesis mainly includes resolution and asymmetric synthesis.

There are two routes for the splitting method. One is to use α-haloacetophenone as the raw material, after amination and reduction, and then chemically split to obtain a single enantiomer product; the second is catechol and chlorine. Acetyl chloride or chloroacetic acid is used as a raw material, and the corresponding racemate is obtained by condensation, amination and reduction, and then separated by tartaric acid to obtain a single enantiomer product. The split method is widely used, but there is a problem that the theoretical yield is less than 50%, and the split S-enantiomer cannot be utilized, and the raw materials are wasted.

The asymmetric synthesis method mainly uses a chiral metal catalyst for hydrogenation reduction to obtain a single configuration product. The commonly used chiral catalysts are expensive transition metals and chiral ligands, and the cost is high, and the environmental pollution is heavier.

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