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M5250

Sigma-Aldrich

Melatonin

powder, ≥98% (TLC)

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

biological source

synthetic (organic)

Quality Level

200

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)

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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.

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品

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Melatonin attenuates stress-induced defecation: lesson from a rat model of stress-induced gut dysfunction.
Song GH
Neurogastroenterology and Motility, 17(5), 744-750 (2005)
Long-term melatonin treatment reduces ovarian mass and enhances tissue antioxidant defenses during ovulation in the rat.
Chuffa LG
Brazilian journal of medical and biological research, 44(3), 217-223 (2011)
Melatonin: a hormone, a tissue factor, an autocoid, a paracoid, and an antioxidant vitamin.
Tan DX
Journal of Pineal Research, 34(1), 75-78 (2003)
Song Ding et al.
Journal of pineal research, 67(2), e12581-e12581 (2019-04-23)
Rupture of vulnerable plaques is the main trigger of acute cardio-cerebral vascular events, but mechanisms responsible for transforming a stable atherosclerotic into a vulnerable plaque remain largely unknown. Melatonin, an indoleamine hormone secreted by the pineal gland, plays pleiotropic roles
Ismail Gögenur et al.
Journal of pineal research, 57(1), 10-15 (2014-04-09)
The aim was to examine the effect of perioperative melatonin treatment on clinical cardiac morbidity and markers of myocardial ischemia in patients undergoing elective surgery for abdominal aortic aneurism. Reperfusion injury results in increased cardiac morbidity in patients undergoing surgery
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