Serotonin → N-Acetylserotonin

Participants

Reaction Steps

Serotonin (compound 7 in Scheme 3) reacts with N-succinimidyl acetate (8) selectively on the primary alkyl amine, as shown below, to give N-acetylserotonin (9). The electroactive hydroxytryptamine ring system emerges from the reaction unchanged. In practice a biological sample of 1.0 ml volume (for example: cerebrospinal fluid) is degassed by bubbling argon and treated with 0.05 ml of a solution of N-succinimidyl acetate in dioxane (100 mg/ml). The reaction is carried out at a pH of 10-11 in a closed vessel under argon at 70° C. for a period as short as five minutes or as long as two hours. The reaction is then quenched with glycine, giving the non-electroactive sodium N-acetylglycinate (10). ##STR5##

Provenance & Evidence