Record Information
Creation date2015-10-09 22:31:40 UTC
Update date2017-01-19 02:36:30 UTC
FoodComEx IDPC000633
FoodDB RecordFDB022505
Chemical Information
DescriptionN-Acetylserotonin is an intermediate in the metabolic pathway of melatonin and indoleamine in the pineal gland of mammalians. Serotonin-N-acetyltransferase (SNAT), which regulates the rate of melatonin biosynthesis in the pineal gland, catalyzes the acetylation of 5HT to N-acetylserotonin (NAS). A methyl group from S-adenosylmethionine is transferred to NAS by hydroxyindole-O-methyltransferase (HIOMT), and finally NAS is converted to 5-methoxy-N-acetyltryptamine, or melatonin. In most mammalian species the content of NAS (and melatonin) in the pineal gland shows clear circadian changes with the highest level occurring during the dark period. This elevation of the contents of NAS (and melatonin) in the dark period is due to the increase of SNAT activity and the elevation of SNAT gene expression. Experimental studies show that N-acetylserotonin possess free radical scavenging activity. Acute administration of irreversible and reversible selective MAO-A inhibitors and high doses (or chronic administration of low doses) of relatively selective MAO-B inhibitors (but not of highly selective MAO-B inhibitors) suppressed MAO-A activity and stimulated N-acetylation of pineal serotonin into N-acetylserotonin, the immediate precursor of melatonin. N-acetylserotonin increase after MAO-A inhibitors might mediate their antidepressive and antihypertensive effects. N-Acetylserotonin is the product of the O-demethylation of melatonin mediated by cytochrome P-450 isoforms: Cytochrome p450, subfamily IIc, polypeptide 19 (CYP2C19, a clinically important enzyme that metabolizes a wide variety of drugs), with a minor contribution from Cytochrome p450, subfamily I, polypeptide (2CYP1A2, involved in O-deethylation of phenacetin). (PMID 15616152, 11103901, 10721079, 10591054) [HMDB]. N-Acetylserotonin is found in many foods, some of which are oregon yampah, barley, ostrich fern, and lovage.
CAS Number1210-83-9
Chemical FormulaC12H14N2O2
IUPAC nameN-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide
InChI IdentifierInChI=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)
Average Molecular Weight218.2518
Monoisotopic Molecular Weight218.105527702
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 400 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
AKSci 7506AH
Cayman Chemical 14535
MetaSci HMDB0001238
Toronto Research Chemicals A179160
Toronto Research Chemicals HMDB0001238