M5250

Melatonin

powder, ≥98% (TLC)

• Synonym(s): N-Acetyl-5-methoxytryptamine
• Empirical Formula (Hill Notation): C₁₃H₁₆N₂O₂
• CAS Number: 73-31-4
• Molecular Weight: 232.28
• Beilstein/REAXYS Number: 205542
• EC Number: 200-797-7
• MDL number: MFCD00005655
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278103
• NACRES: NA.32

Properties

• biological source: synthetic (organic)
• assay: ≥98% (TLC)
• form: powder
• color: white to off-white
• mp: 116.5-118 °C (lit.)
• solubility: ethanol: 50 mg/mL
• storage temp.: −20°C
• SMILES string: COc1ccc2[nH]cc(CCNC(C)=O)c2c1
• 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)
• InChI key: DRLFMBDRBRZALE-UHFFFAOYSA-N
• Gene Information: human ... MTNR1A(4543) , MTNR1B(4544) , NOS1(4842) , NOS2(4843) , NOS2B(201288) , NOS2C(645740) , NOS3(4846)

Description

General description

Melatonin (N-acetyl-5-methoxytryptamine) is synthesized from an essential amino acid tryptophan. It is a pineal gland neurohormone. Direct, non-receptor-mediated free radical scavenging activity induced by melatonin, makes it unique from other classic hormones. Melatonin is expressed in variety of organisms such as bacteria, algae, fungi, plants, insects, and vertebrates including humans.

Application

Melatonin has been administered to experimental animals for following studies:

• To determine if long-term melatonin administration is able to induce reproductive changes and how melatonin exerts its protective action related to lipid oxidation and antioxidant activities in the rat ovary during ovulation.
• To determine the effect of melatonin on endoplasmic reticulum stress and sirtuin 1 expression in neuronal cells of newborn rats after hypoxia–ischemia.
• To study the effect of melatonin on chronic stress-induced gut dysfunction in stressed mice.

Biochem/physiol Actions

Hormone; mediates photoperiodicity in mammals; inhibits cerebellar nitric oxide synthetase; peroxynitrite scavenger. Melatonin has complex effects on apoptotic pathways, inhibiting apoptosis in immune cells and neurons but enhancing apoptotic cell death of cancer cells. Inhibits proliferation/metastasis of breast cancer cells by inhibiting estrogen receptor action.

Melatonin is characterized with variety of properties such as antioxidant, autocoid, paracoid and hormonal properties, as well as anti- inflammatory and anti-apoptotic properties. Melatonin is implicated in the regulation of seasonal reproduction, energy metabolism and thermoregulation in mammals. Melatonin plays a vital role in the lessening of neonatal hypoxia–ischemia (HI) induced endoplasmic reticulum (ER) stress and conserves sirtuin 1( SIRT-1) expression.

Caution

Solutions are light sensitive and subject to oxidation.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)