N-Acetylserotonin

N-Acetylserotonin
Names
Preferred IUPAC name
N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]acetamide
Other names
N-Acetyl-5-hydroxytryptamine
N-Acetyl-5-HT
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.013.560 Edit this at Wikidata
MeSH N-Acetylserotonin N-Acetylserotonin
UNII
  • InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15) checkY
    Key: MVAWJSIDNICKHF-UHFFFAOYSA-N checkY
  • InChI=1/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)
    Key: MVAWJSIDNICKHF-UHFFFAOYAX
  • CC(=O)NCCC1=CNC2=C1C=C(C=C2)O
Properties
C12H14N2O2
Molar mass 218.256 g·mol−1
Density 1.268 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Acetylserotonin (NAS), also known as normelatonin, is a naturally occurring chemical intermediate in the endogenous production of melatonin from serotonin.[1][2] It also has biological activity in its own right, including acting as a melatonin receptor agonist, an agonist of the TrkB, and having antioxidant effects.

  1. ^ AXELROD J, WEISSBACH H (April 1960). "Enzymatic O-methylation of N-acetylserotonin to melatonin". Science. 131 (3409): 1312. Bibcode:1960Sci...131.1312A. doi:10.1126/science.131.3409.1312. PMID 13795316. S2CID 22341451.
  2. ^ WEISSBACH H, REDFIELD BG, AXELROD J (September 1960). "Biosynthesis of melatonin: enzymic conversion of serotonin to N-acetylserotonin". Biochimica et Biophysica Acta. 43: 352–3. doi:10.1016/0006-3002(60)90453-4. PMID 13784117.