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SML2262

Sigma-Aldrich

Ramelteon

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

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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
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
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
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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