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Substance Name: Melatonin
RN: 73-31-4
UNII: JL5DK93RCL
InChIKey: DRLFMBDRBRZALE-UHFFFAOYSA-N

Note

  • A biogenic amine that is found in animals and plants. In mammals, melatonin is produced by the PINEAL GLAND. Its secretion increases in darkness and decreases during exposure to light. Melatonin is implicated in the regulation of SLEEP, mood, and REPRODUCTION. Melatonin is also an effective antioxidant.

Molecular Formula

  • C13-H16-N2-O2

Molecular Weight

  • 232.2814
 

Classification Codes

  • Antioxidants
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Hormone
  • Mutation Data
  • Protective Agents
  • Reproductive Effect
  • Tumor Data

Names and Synonyms

Name of Substance

  • Melatonin

MeSH Heading

  • Melatonin

Synonyms

  • 5-22-12-00042 (Beilstein Handbook Reference)
  • 5-Methoxy-N-acetyltryptamine
  • BRN 0205542
  • CCRIS 3472
  • Circadin
  • EINECS 200-797-7
  • HSDB 7509
  • Melatonin
  • Melatonine
  • N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide
  • N-Acetyl-5-methoxytryptamine
  • NSC 113928
  • UNII-JL5DK93RCL

Systematic Names

  • Acetamide, N-(2-(5-methoxy-1H-indol-3-yl)ethyl)- (9CI)
  • Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)-
  • Melatonin
  • N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide

Mixture Name

  • Guna-dermo

Registry Numbers

CAS Registry Number

  • 73-31-4

FDA UNII

  • JL5DK93RCL

System Generated Number

  • 0000073314

Structure Descriptors

InChI

InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)

InChIKey

DRLFMBDRBRZALE-UHFFFAOYSA-N

Smiles

COc1ccc2[nH]cc(CCNC(=O)C)c2c1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1375mg/kg (1375mg/kg)   Pharmaceutical Chemistry Journal Vol. 17, Pg. 559, 1983.
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02739,
mouse LD50 oral 1250mg/kg (1250mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.
mouse LD50 subcutaneous > 1600mg/kg (1600mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.
rat LD50 intraperitoneal 1131mg/kg (1131mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.
rat LD50 intravenous 356mg/kg (356mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.
rat LD50 oral > 3200mg/kg (3200mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.
rat LD50 subcutaneous > 1600mg/kg (1600mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 117 deg C   EXP
log P (octanol-water) 1.650 (none)   EST
Atmospheric OH Rate Constant 2.12E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.