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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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
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
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)
Saïd El Kazzouli et al.
European journal of medicinal chemistry, 46(9), 4252-4257 (2011-07-19)
A novel class of imidazo[1,2-a]pyridines as melatonin receptor ligands is designed and synthesized. The affinities of 3-(6-methoxy-2-phenylimidazo[1,2-a]pyridine-3-yl)-N-methyl-propionamide 8, N-[2-(6-methoxy-2-phenylimidazo[1,2-a]pyridine-3-yl)-ethyl]-acetamide 13 and N-(1-hydroxy-3-(5-methoxy-2-phenyl-1H-indol-3-yl)propan-2-yl)acetamide 18 are evaluated for binding on melatonin receptors. Compound 8 present good selectivity for MT(2) over MT(1) (MT(1)/MT(2)
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
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