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Sigma-Aldrich

Melatonin

≥99.5%

Synonym(s):

N-Acetyl-5-methoxytryptamine

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About This Item

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:
329757080

assay

≥99.5%

form

powder

mp

116.5-118 °C (lit.)

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

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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)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Mariano Bizzarri et al.
Expert opinion on therapeutic targets, 17(12), 1483-1496 (2013-09-17)
Compelling evidence has highlighted the complex pleiotropic functions elicited by the melatonin in cancer cells. Melatonin behaves as a 'smart killer', i.e., modulating anti-apoptotic processes in normal cells, and triggering pro-apoptotic signals in cancer cells. Melatonin induces programmed cell death
Jack Falcón et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(1), 314-319 (2013-12-20)
Melatonin (N-acetyl-5-methoxytrypamine) is the vertebrate hormone of the night: circulating levels at night are markedly higher than day levels. This increase is driven by precisely regulated increases in acetylation of serotonin in the pineal gland by arylalkylamine N-acetyltransferase (AANAT), the
Juan R Calvo et al.
Journal of pineal research, 55(2), 103-120 (2013-07-31)
Melatonin is the major secretory product synthesized and secreted by the pineal gland and shows both a wide distribution within phylogenetically distant organisms from bacteria to humans and a great functional versatility. In recent years, a considerable amount of experimental
Paul P Drury et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 34(1), 126-135 (2013-10-10)
Melatonin is a naturally occurring indolamine with mild antioxidant properties that is neuroprotective in perinatal animals. There is limited information on its effects on preterm brain injury. In this study, 23 chronically instrumented fetal sheep received 25 minutes of complete umbilical
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