N-acetyl-5-methoxytryptamine

TRYPTAMINE, N-ACETYL-5-METHOXY INDOLE, 3-(2-ACETAMIDOETHYL)-5-METHOXY SEROTONIN, N-ACETYL-O-METHYL ACETAMIDE, N-[2-(5-METHOXYINDOL-3-YL)ETHYL] N-ACETYL-5-METHOXYTRYPTAMINE 3-(2-ACETAMIDOETHYL)-5-METHOXYINDOLE N-ACETYL-O-METHYLSEROTONIN N-[2-(5-METHOXYINDOL-3-YL)ETHYL]ACETAMIDE REGULIN... 

To a solution of 0.2 g 5-methoxytryptamine in 4 mL of glacial HOAc there was added 2.0 mL acetic anhydride and heated at steam-bath temperature for 1 min. The volatiles were removed under vacuum and the residue was ground up under a mixture of and petroleum ether to yield 0.2 g (82%) of a white solid. This, after recrystallization from an ethanol / petroleum ether mixture, provided N-acetyl-5-methoxytryptamine (melatonin) as white crystalline solid with a mp 116-118 °C. MS (in m/z) 173 (100%) indolemethylene+ 160 (97%) parent ion 232 (28%). IR (in cm-1) 713, 794, 825, 925, 1042, 1101, 1177. 

Melatonin N-acetyl-5- methoxytryptamine Manufactured synthetically to mimic the endogenous hormone Sedative-hypnotic regulate sleep-wake cycles used in various other conditions because of antioxidant and immunomodulating effects... 

Melatonin (N-acetyl-5-methoxytryptamine) is a neuro-hormone secreted by the pineal gland from the amino acid precursor L-tryptophan. Its endogenous secretion is photosensitive and has a circadian rhythm—plasma melatonin concentrations are highest at night in both diurnal and nocturnal animals, and fall with age (1). The nocturnal melatonin peak coincides with a drop in body temperature and increased sleepiness in healthy humans. Oral melatonin has a short half-life (30-50 minutes) and extensive first-pass metabolism. Its clearance is reduced in severe liver disease (2). 

Szmuszkovicz, J. Anthony, W.C. Hetzelman, R.V. Synthesis of N-Acetyl-5-methoxytryptamine ... 

Melatonin (N-acetyl-5-methoxytryptamine) synthetic analogs as nitric oxide synthase inhibitors 12MRM600. 

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