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461326

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:
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 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

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
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
P Boyce et al.
Acta psychiatrica Scandinavica. Supplementum, (444)(444), 16-23 (2013-08-09)
Disturbances in circadian rhythms have been associated with major depression and may be an underlying mechanism for the disorder. Resynchronisation of circadian rhythms may provide a new approach to treatment, especially by manipulating melatonin secretion. Melatonin is secreted at night
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
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