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Basic information

  • Name:
  • Melatonine

  • CAS No.:
  • 73-31-4

  • Formula:
  • C13H16N2O2
  • Synonyms:
  • N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide;N-Acetyl-5-methoxytryptamine;5-Methoxy-N-acetyltryptamine;Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)-;acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-;N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide;Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]- (6CI,8CI);Melovine;Acetamide, N-[2- (5-methoxy-1H-indol-3-yl)ethyl]-;Melatonin;Acetamide, {N-[2-(5-methoxyindol-3-yl)ethyl]-};Circadin;Acetamide,N-[2-(5-methoxy-1H-indol-3-yl)- ethyl]-;Prestwick_312;Acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]- (9CI);Melatonin (MLT);
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Chemistry

IUPAC name: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide
Following is the Structure of Melatonin (CAS NO.73-31-4):
              
Molecular formula: C13H16N2O2
Melatonin's Molar mass: 232.278 g/mol 
EINECS: 200-797-7
Melting point: 116.5-118 °C(lit.)
Density: 1.175 g/cm3
Flash Point: 264 °C  
storage temp.: -15 °C 
Index of Refraction: 1.6
Surface Tension: 46.6 dyne/cm
Enthalpy of Vaporization: 78.41 kJ/mol
Boiling Point: 512.8 °C at 760 mmHg
Vapour Pressure: 1.25E-10 mmHg at 25 °C
Appearance of Melatonin (CAS NO.73-31-4): Off-White Powder
Product Categories: Heterocyclic Series; Heterocycles series; Indoles; Tryptamines; Nutritional Supplements; Intermediates & Fine Chemicals; Pharmaceuticals; Melatonin receptor
Canonical SMILES: CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC
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

History

  Melatonin (CAS NO.73-31-4) is related to the mechanism by which some amphibians and reptiles change the color of their skin and, indeed, it was in this connection the substance first was discovered. McCord and Allen discovered (J Exptl Zool, 1917) that extract of the pineal glands of cows lightened frog skin, while Aaron B. Lerner is credited for naming the hormone and for defining its chemical structure in 1958. In the mid-70s Lynch et al. demonstrated that also in humans the production of melatonin exhibits a circadian rhythm.

Uses

 Melatonin (CAS NO.73-31-4) is important in the regulation of the circadian rhythms of several biological functions.The primary motivation for the use of melatonin as a supplement may be as a natural aid to better sleep.
Many biological effects of melatonin are produced through activation of melatonin receptors, while others are due to its role as a pervasive and powerful antioxidant with a particular role in the protection of nuclear and mitochondrial DNA. Melatonin have been available as a dietary supplement.
Several clinical studies indicate that supplementation with melatonin is an effective preventive treatment for migraines and cluster headaches. It has been shown to be effective in treating one form of depression, seasonal affective disorder, and is being considered for bipolar and other disorders where circadian disturbances are involved. Melatonin is involved in the regulation of body weight, and may be helpful in treating obesity.
Histologically, it is believed that melatonin has some effects for sexual development in higher organisms.

Toxicity Data With Reference

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.

 Melatonin (CAS NO.73-31-4) has a very low toxicity in rats. Rat maternal toxicity: the no observable adverse effect level (NOAEL) and lowest observed adverse effect level (LOAEL) were 100 and 200 mg/kg/day, respectively, and the developmental toxicity NOAEL was >= 200 mg/kg/day.

Safety Profile

Hazard Codes: Toxic
Risk Statements: 60 
R60: May impair fertility.
Safety Statements: 24/25
S24/25: Avoid contact with skin and eyes. 
WGK Germany: 2 
RTECS: AC5955000
F: 8-10-23

Specification

 Melatonin , with a CAS number of 73-31-4, also known as N-(2-(5-methoxyindol-3-yl)ethyl)acetamide ; N-Acetyl-5-methoxytryptamine ; and 3-(N-Acetyl-2-aminoethyl)-5-methoxyindole. It is a naturally occurring hormone found in animals and in some other living organisms, including algae. Antioxidants; Central Nervous System Agents; Central Nervous System; Depressants; Drug / Therapeutic Agent; Hormone; Mutation data; Protective Agents; Reproductive Effect and Tumor data.

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