propanamide, N-[2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]-
ramelteon
CAS: 196597-26-9
Molecular Formula: C16H21NO2
propanamide, N-[2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]- - Names and Identifiers
| Name | ramelteon |
| Synonyms | TAK-375 TAK375 CS-1962 ROZEREM TAK 375 ramelteon rac Rozerem rac Ramelteon UNII-901AS54I69 N-{2-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]fur-8-yl]ethyl}propanamid N-{2-[(8S)-1,6,7,8-tétrahydro-2H-indéno[5,4-b]fur-8-yl]éthyl}propanamide N-[2-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propanamide N-{2-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl}propanamide propanamide, N-[2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]- rac N-[-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propanamide N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl]propanamide |
| CAS | 196597-26-9 |
| EINECS | 200-835-2 |
| InChI | InChI=1/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 |
| InChIKey | YLXDSYKOBKBWJQ-LBPRGKRZSA-N |
propanamide, N-[2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]- - Physico-chemical Properties
| Molecular Formula | C16H21NO2 |
| Molar Mass | 259.34 |
| Density | 1.119±0.06 g/cm3(Predicted) |
| Melting Point | 113-1150C |
| Boling Point | 455.3±24.0 °C(Predicted) |
| Specific Rotation(α) | D20 -57.8° (c = 1.004 in chloroform) |
| Flash Point | 2℃ |
| Solubility | DMSO : 25 mg/mL mother liquor preservation: sub-package and freeze storage to avoid repeated freezing and thawing;-20 ℃,1 month;-80 ℃,6 months (after dilution, the solution temperature is low and storage may precipitate, try to use the current mixture) Cell experiment: dissolve with DMSO first, then dilute with culture medium |
| Vapor Presure | 1.77E-08mmHg at 25°C |
| Appearance | Crystalline solid |
| Color | Crystalline |
| pKa | 16.37±0.46(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.555 |
| Use | a melatonin MT1/MT2 receptor agonist. |
| In vitro study | Ramelteon acts on CHO cells to inhibit forskolin-stimulated cAMP production in a concentration-dependent manner with an IC50 of 21.2 pM. Ramelteon acts on recombinant MT1 and MT2 receptors with high affinity, and pK I is 10.05 and 9.70, respectively. Ramelteon inhibits melanocyte cytochrome granule aggregation in Xenopus laevis with a pEC50 of 11.48. Ramelteon (1 nM) not only increased ERK1/2 phosphate phosphorylation in MT1/MT2 cerebellar granule cells, but also increased ERK1/2 phosphate phosphorylation in cerebellar granule cells containing only one melatonin receptor. 4P-PDOT acts on MT1 KO cerebellar granule cells and prevents the stimulatory effect of Ramelteon (1 nM), while Luzindole acts on MT2 KO cerebellar granule cells and reduces the effect of Ramelteon (1 nM). |
| In vivo study | Ramelteon, administered intraperitoneally to rats at a dose of 10 mg/kg, significantly reduced non-rapid eye movement (NREM) sleep latency (time from injection to appearance of NREM sleep). Ramelteon (10 mg/kg, I. P.) also transiently increased NREM sleep time, but the NREM power spectrum was unchanged. Ramelteon, administered orally to rats at doses of 0.1 mg/kg and 1 mg/kg, accelerated the rhythm of the day-night cycle, but did not affect learning or memory. Oral administration of Ramelteon at doses of 0.03 mg/kg and 0.3 mg/kg to freely moving monkeys significantly shortened delayed sleep and increased total sleep time, but did not affect the daily behavior of monkeys. |
propanamide, N-[2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]- - Risk and Safety
| Risk Codes | R11 - Highly Flammable R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36 - Irritating to the eyes |
| Safety Description | S16 - Keep away from sources of ignition. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN 1648 3 / PGII |
| WGK Germany | 2 |
propanamide, N-[2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]- - Reference
| Reference Show more | 1. Wang Ling, Wang Yujiang, Zhou Qing, Sun Shipeng, Sun Aili, Xu Shuiying, Zhao Yujing, Li Xin, Sun Chengwen. Determination and clinical application of lemeteinamide in human plasma by gas-mass spectrometry [J]. Chinese Journal of Hospital Pharmacy, 2020,40(22):2322-2326. |
propanamide, N-[2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]- - Introduction
Ramelteon is the first in a new class of sleep agents that selectively binds to the MT1 and MT2 receptors in the suprachiasmatic nucleus (SCN), instead of binding to GABAA receptors, such as with drugs like zolpidem. Ramelteon is approved by the U.S. Food and Drug Administration (FDA) for long-term use. Ramelteon does not show any appreciable binding to GABAA receptors, which are associated with anxiolytic, myorelaxant, and amnesic effects. Ramelteon is a melatonin receptor agonist with both high affinity for melatonin MT1 and MT2 receptors and selectivity over the MT3 receptor.
Last Update：2022-10-16 17:14:45
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