M2675
Melatonin
97%
Synonym(s):
N-Acetyl-5-methoxytryptamine
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About This Item
Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
Molecular Weight:
232.28
EC Number:
200-797-7
UNSPSC Code:
12352100
MDL number:
Beilstein/REAXYS Number:
205542
assay
97%
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
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Silvia Rivara et al.
Journal of medicinal chemistry, 48(12), 4049-4060 (2005-06-10)
Three-dimensional homology models of human MT(1) and MT(2) melatonin receptors were built with the aim to investigate the structure-activity relationships (SARs) of MT(2) selective antagonists. A common interaction pattern was proposed for a series of structurally different MT(2) selective antagonists
Annalida Bedini et al.
Journal of medicinal chemistry, 54(24), 8362-8372 (2011-11-04)
New derivatives of 4-phenyl-2-propionamidotetralin (4-P-PDOT) were prepared and tested on cloned MT1 and MT2 receptors, with the purpose of merging previously reported pharmacophores for nonselective agonists and for MT2-selective antagonists. A 8-methoxy group increases binding affinity of both (±)-cis- and
Tatsuki Koike et al.
Journal of medicinal chemistry, 54(12), 4207-4218 (2011-05-17)
Novel tricyclic dihydrofuran derivatives were designed, synthesized, and evaluated as melatonin receptor (MT(1)/MT(2)) ligands based on the previously reported 1,6-dihydro-2H-indeno[5,4-b]furan 1a. By screening the central tricyclic cores, we identified 8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine as a potent scaffold with a high ligand-lipophilicity efficiency (LLE)
Tatsuki Koike et al.
Journal of medicinal chemistry, 54(9), 3436-3444 (2011-04-09)
A novel series of 1,6-dihydro-2H-indeno[5,4-b]furan derivatives were designed and synthesized as MT(2)-selective ligands. This scaffold was identified as a potent mimic of the 5-methoxy indole core of melatonin, and introduction of a cyclohexylmethyl group at the 7-position of this scaffold
Zhivko A Velkov et al.
European journal of medicinal chemistry, 44(7), 2834-2839 (2009-01-27)
Experimental and theoretical investigation of the antioxidant activity of melatonin is carried out. The theoretical approach comprises the evaluation of several appropriate descriptors of scavenging activity with the help of quantum-chemistry methods. The values obtained are compared with available data
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