M5250

Sigma-Aldrich

Melatonin

powder, ≥98% (TLC)

Synonym(s):
N-Acetyl-5-methoxytryptamine
Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
Molecular Weight:
232.28
Beilstein/REAXYS Number:
205542
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32
Pricing and availability is not currently available.

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

COc1ccc2nHcc(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.

Packaging

250 mg in glass bottle
1, 5, 10 g in glass bottle

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Caution

Solutions are light sensitive and subject to oxidation.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M5250.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
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)
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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