[CH:1]1[C:6]([OH:7])=[CH:5][C:4]2[C:8]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:10][C:3]=2[CH:2]=1.Cl.N1C=CC=CC=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].[OH-].[Na+]>C(O)(=O)C.C(O)(C)C>[CH3:22][C:21]([NH:13][CH2:12][CH2:11][C:8]1[C:4]2[CH:5]=[C:6]([OH:7])[CH:1]=[CH:2][C:3]=2[NH:10][CH:9]=1)=[O:23]N-acetyl serotonin was synthesized as follows. 100 mg (0.47 mmol) serotonin hydrochloride and 10 mL of pyridine were mixed in a 100 mL round-bottomed flask, and the solution was cooled to 0° C. under argon. Acetic anhydride (2.84 g, 28.4 mmol) was added slowly over 1 hr. After stirring at 0° C. for 20 hr the reaction was terminated by removing the volatile reagents under high vacuum. The remaining syrup was dissolved into 25 mL of methylene chloride and washed with 0.1 M HCl until the pH of the aqueous phase was less than 3. The organic phase was dried under anhydrous sodium sulfate, filtered and concentrated to yield a syrup. To this syrup was added 25 mL of aqueous isopropyl alcohol (50 wt%) and the solution was cooled to 0° C. Sodium hydroxide (1 mL of a 1.0 mM solution) was added and stirred at 0° C. for 4 hr. The solution was neutralized with acetic acid, concentrated and filtered through a short plug of silica gel with ether, concentrated and recrystallized from benzene/chloroform to yield 27 mg (0.11 mmol) of N-acetyl serotonin.
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