[CAS NO. 196597-26-9] Ramelteon

Name: Ramelteon
Brand: Arctom Scientific
SKU: SLK-S1259

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PRODUCTS SPECIFICATIONS [196597-26-9]

Distributor

Catalog

SLK-S1259

Brand

Selleck

CAS

196597-26-9

DESCRIPTION [196597-26-9]

Overview

MDL	MFCD08067736
Molecular Weight	259.34
Molecular Formula	C16H21NO2
SMILES	C(CNC(CC)=O)[C@H]1C=2C3=C(C=CC2CC1)OCC3

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Preparing Stock Solutions

Concentration Volume Mass	1 mg	5 mg	10 mg
1 mM	3.8559 mL	19.2797 mL	38.5594 mL
5 mM	0.7712 mL	3.8559 mL	7.7119 mL
10 mM	0.3856 mL	1.9280 mL	3.8559 mL
50 mM	0.0771 mL	0.3856 mL	0.7712 mL

Description

Ramelteon (TAK-375) is a novel agonist for human MT1 and MT2 receptors and chick forebrain melatonin receptors with of 14 pM, 112 pM and 23.1 pM, respectively.

Features

A tricyclic synthetic analog of melatonin.

Targets

MT1 receptor ^[1] (Cell-free assay)	MT receptor (chicken) ^[1] (Cell-free assay)	MT2 receptor ^[1] (Cell-free assay)
14 pM(Ki)	23.1 pM(Ki)	112 pM(Ki)

In vitro

Ramelteon inhibits forskolin-stimulated cAMP production with IC50 of 21.2 pM in CHO cells. Ramelteon has high affinity with recombinant human MT1 and MT2 receptors with pKi of 10.05 and 9.70, respectively. Ramelteon inhibits Xenopus laevis melanophore pigment granule aggregation with pEC50 of 11.48. Ramelteon (1 nM) increases ERK1/2 phosphorylation not only in MT1/MT2 cerebellar granule cells but also in cerebellar granule cells expressing only one of the two melatonin receptors. 4P-PDOT blocks the stimulatory action of Ramelteon (1 nM) in MT1 KO cerebellar granule cells, while luzindole attenuates the action of Ramelteon (1 nM) in MT2 KO cerebellar granule cells. Ramelteon (100 μM) induces any pigment dispersion while melatonin completely disperses aggregated melanophores at 10 μM.

In vivo

Ramelteon (10 mg/kg, i/p) significantly reduces NREM sleep latency in rat and also produces a short-lasting increase in nonrapid eye movement (NREM) sleep duration, but the NREM power spectrum is unaltered. Ramelteon (0.1 mg/kg and 1 mg/kg, p.o.) accelerates reentrainment of running wheel activity rhythm to the new lightdark cycle in rats without affecting learning or memory. Ramelteon (0.03 mg/kg and 0.3 mg/kg, p.o.) significantly shortens latency to sleep onset and significantly increases total duration of sleep in freely moving monkeys without affecting the general behavior of the monkeys.

References

[1] Kato K, et al. Neuropharmacology, 2005, 48(2), 301-310.
[2] Fisher SP, et al. J Pineal Res, 2008, 45(2), 125-132.
[3] Imbesi M, et al. Neuroscience, 2008, 155(4), 1160-1164.
[4] Hirai K, et al. J Biol Rhythms, 2005, 20(1), 27-37.
[5] Yukuhiro N, et al. Brain Res, 2004, 1027(1-2), 59-66.

Synonyms

Propanamide, N-[2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]-

Propanamide, N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]-, (S)-

N-[2-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propanamide

TAK 375

Ramelteon

(S)-N-[2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide

Rozerem

(S)-N-[2-(1,6,7,8-Tetrahydro-2H-indeno-[5,4-b]furan-8-yl)ethyl]propionamide

Rozerm