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SML2262

Ramelteon

Name: Ramelteon
Brand: SIGMA

Synonym(s):

Ramelteon solution, (S)-N-[2-(1,6,7,8-Tetrahydro-2H-indeno-[5,4-b]furan-8-yl)ethyl]propionamide, N-[2-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propanamide, TAK 375, TAK-375

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₂₁NO₂

CAS Number:

196597-26-9

Molecular Weight:

259.34

MDL number:

MFCD08067736

UNSPSC Code:

12352200

NACRES:

NA.77

form

powder

optical activity

[α]/D -50 to -60°, c = 1.0 in chloroform-d

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CCC(NCC[C@H]1C(C(CCO2)=C2C=C3)=C3CC1)=O

InChI

1S/C16H21NO2/c1-2-15(18)17-9-7-12-4-3-11-5-6-14-13(16(11)12)8-10-19-14/h5-6,12H,2-4,7-10H2,1H3,(H,17,18)/t12-/m0/s1

InChI key

YLXDSYKOBKBWJQ-LBPRGKRZSA-N

Gene Information

human ... MTNR1A(4543) , MTNR1B(4544)

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Biochem/physiol Actions

Ramelteon is a cell penetrant, potent and selective agonist at MT1/MT2 melatonin receptor that exhibits sleep-promoting properties. It is not binding to GABA receptor complex. Ramelteon is an analog of melatonin recently approved to treat insomnia.

Pictograms

GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Ramelteon (TAK-375), a selective MT1/MT2-receptor agonist, reduces latency to persistent sleep in a model of transient insomnia related to a novel sleep environment.

Thomas Roth et al.

Sleep, 28(3), 303-307 (2005-09-22)

Evaluate the efficacy of ramelteon, an MT/1MT2-receptor agonist, for the treatment of transient insomnia in healthy adults. Randomized, double-blind, placebo-controlled design using a model of transient insomnia related to sleeping in a novel environment. Fourteen sleep research centers. Healthy adults

Melatonin Receptor Agonists as the "Perioceutics" Agents for Periodontal Disease through Modulation of Porphyromonas gingivalis Virulence and Inflammatory Response.

Wei Zhou et al.

PloS one, 11(11), e0166442-e0166442 (2016-11-11)

"Perioceutics" including antimicrobial therapy and host modulatory therapy has emerged as a vital adjunctive treatment of periodontal disease. Melatonin level was significantly reduced in patients with periodontal diseases suggesting melatonin could be applied as a potential "perioceutics" treatment of periodontal

Ramelteon Improves Post-traumatic Stress Disorder-Like Behaviors Exhibited by Fatty Acid-Binding Protein 3 Null Mice.

Yasushi Yabuki et al.

Molecular neurobiology, 55(4), 3577-3591 (2017-05-19)

We previously reported that fatty acid-binding protein 3 (FABP3) knockout (Fabp3

Ramelteon ameliorated 1-methyl-4-phenylpyridinium (MPP+)-induced neurotoxicity in neuronal cells in a mitochondrial-dependent pathway.

Chuo Li et al.

Bioengineered, 12(1), 4868-4877 (2021-08-05)

Parkinson's disease (PD) is a common neurodegenerative disease with global health and economic impact. 1-methyl-4-phenylpyridinium (MPP+)-induced mitochondrial dysfunction and oxidative stress are reported to participate in the pathological mechanism of PD. Ramelteon is a novel oral hypnotic agent that has

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