Compound: Ramelteon
SMILES: O=C(NCC[C@H]1c2c3c(OCC3)ccc2CC1)CC
InChIKey: YLXDSYKOBKBWJQ-LBPRGKRZSA-N
Synonyms: Ramelteon, 196597-26-9, Rozerem, TAK-375, TAK375, (S)-N-(2-(1,6,7,8-tetrahydro-2H-indeno-(5,4)furan-8-yl)ethyl)propionamide, 901AS54I69, DTXSID6045951, N-{2-[(8S)-1H,2H,6H,7H,8H-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)-, ramelteonum, N-(2-((8S)-1H,2H,6H,7H,8H-indeno(5,4-b)furan-8-yl)ethyl)propanamide, N-(2-((8S)-2,6,7,8-tetrahydro-1H-cyclopenta(e)(1)benzoxol-8-yl)ethyl)propanamide, N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzoxol-8-yl]ethyl]propanamide, RefChem:55966, N05CH02, DTXCID301508624, (S)-N-[2-(1,6,7,8-tetrahydro-2H-indeno-[5,4-b]furan-8-yl)ethyl]propionamide, (S)-N-(2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl)propionamide, N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl]propanamide, MFCD08067736, CHEMBL1218, Ramelteon [USAN], 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, N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e]benzofuran-8-yl]ethyl]propanamide, SMR002544684, Rozerem (TN), SR-05000001957, Ramelteon (JAN/USAN/INN), s1259, UNII-901AS54I69, HSDB 7787, (S)-N-(2-[1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl)propionamide, (S)-N-[2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide, Ramelteon [USAN:INN:BAN:JAN], JEV, Ramelteon (Standard), Ramelteon Impurity 72, RAMELTEON [INN], RAMELTEON [JAN], RAMELTEON [HSDB], RAMELTEON [VANDF], Ramelteon (TAK-375), RAMELTEON [MART.], RAMELTEON [WHO-DD], (-)-N-(2-(((8S)-1,6,7,8-Tetrahydro-2H-indeno(5,4-b)furan-8-yl)ethyl)propanamide, SCHEMBL29237, BSPBio_002318, MLS003915619, MLS006010029, TAK-375SL, SPECTRUM1505817, GTPL1356, orb1308555, RAMELTEON [ORANGE BOOK], SCHEMBL29380213, HY-A0014R, CHEBI:109549, YLXDSYKOBKBWJQ-LBPRGKRZSA-N, GLXC-90176, HMS1922H18, HMS2093F12, HMS3884K07, HY-A0014, MSK11174, BDBM50118470, EBC-08367, Ramelteon 1.0 mg/ml in Acetonitrile, AKOS015895741, AC-5275, CCG-213557, CS-0382, DB00980, FR27673, (S)-N-(2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethyl)propionamide, NCGC00095187-08, NCGC00095187-09, NCGC00178707-03, NCGC00178707-05, AS-15740, DA-57347, SBI-0206874.P001, NS00069667, R0216, SW219712-1, D02689, EN300-219936, AB01274760-01, AB01274760_02, AB01274760_03, Q417689, SR-05000001957-1, SR-05000001957-3, BRD-K28761891-001-01-0, BRD-K28761891-001-04-4, BRD-K28761891-001-09-3, BRD-K28761891-001-10-1, Z2037281108, (S)-N-(2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl)propanamide, N-[2-(1,6,7,8-Tetrahydro-2H-3-oxa-as-indacen-8-yl)-ethyl]-propionamide(S)-(-)-22b, (-)-N-(2-(((8S)-1,6,7,8-TETRAHYDRO-2H-INDENO(5,4-.BETA.)FURAN-8-YL)ETHYL)PROPANAMIDE, PROPANAMIDE, N-(2-((8S)-1,6,7,8-TETRAHYDRO-2H-INDENO(5,4-.BETA.)FURAN-8-YL)ETHYL)-
Theoretical properties:
molecular_formula: C16H21NO2
molecular_weight: 259.34 g/mol
exact_mass: 259.157228913 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 4
heavy_atom_count: 19
topological_polar_surface_area: 38.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from ethyl acetate
color: Crystals from ethyl acetate
melting_point: 113-115 °C
solubility: 1.64e-02 g/L
Descriptions:
pubchem: N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e]benzofuran-8-yl]ethyl]propanamide is a member of indanes.
chembl: RAMELTEON is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Ramelteon, sold under the brand name Rozerem among others, is a melatonin agonist medication which is used in the treatment of insomnia. It is indicated specifically for the treatment of insomnia characterized by difficulties with sleep onset. It reduces the time taken to fall asleep, but the degree of clinical benefit is small. The medication is approved for long-term use. Ramelteon is taken by mouth.
Side effects of ramelteon include somnolence, dizziness, fatigue, nausea, exacerbated insomnia, and changes in hormone levels. Ramelteon is an analogue of melatonin and is a selective agonist of the melatonin MT1 and MT2 receptors. The half-life and duration of ramelteon are much longer than those of melatonin. Ramelteon is not a benzodiazepine or Z-drug and does not interact with GABA receptors, instead having a distinct mechanism of action.
Ramelteon was first described in 2002 and was approved for medical use in 2005. Unlike certain other sleep medications, ramelteon is not a controlled substance in nearly every country and has no known potential for misuse.