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M5250

Sigma-Aldrich

Melatonin

powder, ≥98% (TLC)

Synonyme(s) :

N-Acetyl-5-methoxytryptamine

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About This Item

Formule empirique (notation de Hill):
C13H16N2O2
Numéro CAS:
73-31-4
Poids moléculaire :
232.28
Numéro Beilstein :
205542
Numéro CE :
200-797-7
Numéro MDL:
MFCD00005655
Code UNSPSC :
12352200
ID de substance PubChem :
24278103
Nomenclature NACRES :
NA.32

Source biologique

synthetic (organic)

Niveau de qualité

200

Pureté

≥98% (TLC)

Forme

powder

Couleur

white to off-white

Pf

116.5-118 °C (lit.)

Solubilité

ethanol: 50 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

DRLFMBDRBRZALE-UHFFFAOYSA-N

Informations sur le gène

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

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Catégories apparentées

Description générale

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.

Actions biochimiques/physiologiques

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.

Attention

Solutions are light sensitive and subject to oxidation.

Autres remarques

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

06693

Timestrip Plus™ -20 °C

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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N-Acetyl-5-methoxytryptamine-α,α,β,β-d4 98 atom % D, 98% (CP)

Sigma-Aldrich

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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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