Ramelteon

Ramelteon is a highly potent and selective melatonin receptor agonist with Ki values of 14 and 112 pM for human melatonin1 and melatonin2.

Product information

CAS Number: 196597-26-9

Molecular Weight: 259.34

Formula: C16H21NO2

Synonym:

TAK-375

TAK 375

TAK375

Rozerem

Chemical Name: N-{2-[(8S)-1H,2H,6H,7H,8H-indeno[5,4-b]furan-8-yl]ethyl}propanamide

Smiles: CCC(=O)NCC[C@@H]1CCC2=CC=C3OCCC3=C21

InChiKey: YLXDSYKOBKBWJQ-LBPRGKRZSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : ≥ 50 mg/mL (192.80 mM)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Ramelteon shows very high affinity for human melatonin1 and melatonin2 receptors (expressed in CHO cells), and chick forebrain melatonin receptors (consisting of melatonin1 and melatonin2 receptors) with Ki values of 14.0, 112, and 23.1 pM, respectively. The affinity of ramelteon for hamster brain melatonin3 binding sites is extremely weak (Ki: 2.65 μM) compared to melatonin's affinity for the melatonin3 binding site Ki: 24.1 nM). In addition, ramelteon shows no measurable affinity for a large number of ligand binding sites (including benzodiazepine receptors, dopamine receptors, opiate receptors, ion channels, and transporters) and no effect on the activity of various enzymes. Ramelteon inhibits forskolin-stimulated cAMP production in the CHO cells that express the human melatonin1 and melatonin2 receptors.

In Vivo:

Ramelteon significantly decreases wakefulness at doses of 0.001, 0.01, and 0.1 mg/kg, increases slow-wave sleep at doses of 0.001, 0.01, and 0.1 mg/kg, and increases rapid eye movement sleep at a dose of 0.1 mg/kg in freely moving cats. Ramelteon is associated with reduced subjective sleep latency and improved sleep quality. Ramelteon is associated with improvement in latency to persistent sleep, sleep efficiency , and total sleep time. Ramelteon (10 mg/kg, i/p), administered close to the mid-point of the dark phase of the L:D cycle, significantly reduces NREM sleep latency (time from injection to the appearance of NREM sleep). Ramelteon also produces a short-lasting increase in NREM sleep duration, but the NREM power spectrum is unaltered.

References:

1. Kato K, et al. Neurochemical properties of ramelteon (TAK-375), a selective MT1/MT2 receptor agonist. Neuropharmacology. 2005 Feb;48(2):301-10.
2. Miyamoto M, et al. The sleep-promoting action of ramelteon (TAK-375) in freely moving cats. Sleep. 2004 Nov 1;27(7):1319-25.
3. Kuriyama A, et al. Ramelteon for the treatment of insomnia in adults: a systematic review and meta-analysis. Sleep Med. 2014 Apr;15(4):385-92.
4. Fisher SP, et al. Acute sleep-promoting action of the melatonin agonist, ramelteon, in the rat. J Pineal Res. 2008 Sep;45(2):125-32.

Products are for research use only. Not for human use.