M5250

Melatonin

Name: Melatonin
Brand: SIGMA

powder, ≥98% (TLC)

Synonym(s):

N-Acetyl-5-methoxytryptamine

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All Photos(4)

About This Item

Empirical Formula (Hill Notation):

C₁₃H₁₆N₂O₂

CAS Number:

73-31-4

Molecular Weight:

232.28

UNSPSC Code:

12352200

NACRES:

NA.32

PubChem Substance ID:

24278103

EC Number:

200-797-7

Beilstein/REAXYS Number:

205542

MDL number:

MFCD00005655

biological source:

synthetic (organic)

form:

powder

assay:

≥98% (TLC)

Product Name

Melatonin, powder, ≥98% (TLC)

InChI key

DRLFMBDRBRZALE-UHFFFAOYSA-N

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)

SMILES string

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

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

Quality Level

200

Gene Information

human ... MTNR1A(4543), MTNR1B(4544), NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)

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Related Categories

Cell Culture & Analysis

Cell Culture Supplements & Reagents

Hormones

Molecular Biology & Functional Genomics

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.

Disclaimer

Solutions are light sensitive and subject to oxidation.

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.

Other Notes

This product is not tested for cell culture. End users must qualify this product for their respective applications.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000517620

0000510878

0000503308

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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)

Melatonin stabilizes rupture-prone vulnerable plaques via regulating macrophage polarization in a nuclear circadian receptor RORα-dependent manner.

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

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 reduces cardiac morbidity and markers of myocardial ischemia after elective abdominal aortic aneurism repair: a randomized, placebo-controlled, clinical trial.

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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