Compound: Melatonin
SMILES: O=C(NCCc1c2c(ccc(c2)OC)[nH]c1)C
InChIKey: DRLFMBDRBRZALE-UHFFFAOYSA-N
Synonyms: Melatonin, 73-31-4, Melatonine, N-Acetyl-5-methoxytryptamine, N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide, Circadin, 5-Methoxy-N-acetyltryptamine, Melatol, N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide, Melovine, Melapure, Acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-, N-[2-(5-methoxyindol-3-yl)ethyl]acetamide, N-acetyl-5-methoxy-tryptamine, N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide, NSC 113928, DTXSID1022421, Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)-, JL5DK93RCL, Acetamide, N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-, NSC-56423, 5-methoxy n-acetyl-tryptamine, NSC-113928, J5.258B, BCI-049, NSC113928, Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]-, DTXCID002421, CHEBI:16796, NSC56423, N-[2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide, somease, Heidadouppi, Melaxen, Travelag, Vytalonin, Icenia, Vespro, General nutrit, Natures bounty, Quality health, Health aid, Amerix Melatonin, Life ext, Nature's blend, Safrel Melatonin, S.gard, Melatonin Phenolic, Melatonin 1527, Therapeutic Melatonin, MELATONIN CORD, RefChem:5990, MAX Sleep Junior Childrens SLEEP AID, 200-797-7, NSC-302012, Regulin, 8041-44-9, MFCD00005655, 3-(n-acetyl-2-aminoethyl)-5-methoxyindole, CHEMBL45, Melatonex, Melatonin (JAN), CAS-73-31-4, NCGC00015680-11, MELATONIN [JAN], S1204, M02088, Posidorm, Primex, WLN: T56 BMJ D2MV1 GO1, [3H]melatonin, Melatonina (TN), [3H]-melatonin, ML1, SMR000326666, CCRIS 3472, N-(2-(5-methoxyindol-3-yl)ethyl)-Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]-Acetamide, SR-01000075559, EINECS 200-797-7, UNII-JL5DK93RCL, BRN 0205542, [3H]MLT, Melatonine?, Guna-dermo, Melatonin CRS, HSDB 7509, Melatobel (TN), TNP00300, Prestwick_312, N-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-acetamide, Spectrum_000185, MELATONIN [DSC], Guna-dermo (Salt/Mix), MELATONIN [MI], MELATONIN [HSDB], Prestwick0_000458, Prestwick1_000458, Prestwick2_000458, Prestwick3_000458, Spectrum2_001344, Spectrum3_001393, Spectrum4_000066, Spectrum5_001745, Lopac-M-5250, MELATONIN [VANDF], M1105, Melatonin [EP monograph], ChemDiv2_003916, MELATONIN [MART.], M 5250, M-1200, Melatonin, >=99.5%, MELATONIN [USP-RS], MELATONIN [WHO-DD], Lopac0_000787, Oprea1_104553, Oprea1_814234, SCHEMBL19018, BSPBio_000536, BSPBio_003006, GTPL224, KBioGR_000591, KBioSS_000665, MELATONIN [EMA EPAR], 5-22-12-00042 (Beilstein Handbook Reference), Acetamide, {N-[2-(5-methoxyindol-3-yl)ethyl]-}, MLS000859594, MLS001055382, MLS001240204, BIDD:ER0618, DivK1c_000353, SPECTRUM1500690, Melatonin - Bio-X trade mark, N -Acetyl-5-methoxytryptamine, SPBio_001527, SPBio_002475, Melatonin (synth.) ultra-pure, MELATONIN [GREEN BOOK], BDBM9019, BPBio1_000590, GTPL1357, orb1307851, orb3025362, Acetamide, {N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-}, SCHEMBL29349848, HMS501B15, KBio1_000353, KBio2_000665, KBio2_003233, KBio2_005801, KBio3_002226, Melatonin 1.0 mg/ml in Methanol, NINDS_000353, GLXC-25215, HMS1380B22, HMS1569K18, HMS1921E04, HMS2089F09, HMS2096K18, HMS2233D23, HMS3262M16, HMS3370J20, HMS3413P14, HMS3654A22, HMS3677P14, HMS3713K18, HMS3884M05, HMS5079K15, HMS6019H04, Melatonin (synth.) standard-grade, HY-B0075, MSK10126, Tox21_110195, Tox21_201527, Tox21_302926, Tox21_500787, CCG-38837, EBC-08635, HSCI1_000400, Melatonin for system suitability CRS, Melatonin, powder, >=98% (TLC), SBB003265, STK386880, AKOS000276269, Tox21_110195_1, CS-1769, DB01065, FA01297, KS-1454, LP00787, SDCCGMLS-0065812.P001, SDCCGMLS-0065812.P002, SDCCGSBI-0050765.P003, IDI1_000353, IDI1_002631, SMP2_000309, N-acetyl-5-methoxy-tryptamine Melatonine, NCGC00015680-01, NCGC00015680-02, NCGC00015680-03, NCGC00015680-04, NCGC00015680-05, NCGC00015680-06, NCGC00015680-07, NCGC00015680-08, NCGC00015680-09, NCGC00015680-10, NCGC00015680-12, NCGC00015680-13, NCGC00015680-14, NCGC00015680-15, NCGC00015680-16, NCGC00015680-18, NCGC00015680-34, NCGC00015680-35, NCGC00090727-01, NCGC00090727-02, NCGC00090727-03, NCGC00090727-04, NCGC00090727-05, NCGC00090727-06, NCGC00090727-07, NCGC00090727-08, NCGC00090727-09, NCGC00256404-01, NCGC00259077-01, NCGC00261472-01, AC-10019, BA164660, NCI60_004378, ST057260, SY051401, AB00053279, EU-0100787, NS00009598, SW196607-4, C01598, D08170, AB00053279-10, AB00053279_12, EN300-6486827, {N-[2-(5-methoxyindol-3-yl)ethyl]-} Acetamide, L001261, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-Acetamide, Q180912, SR-01000075559-1, SR-01000075559-6, SR-01000075559-7, SR-01000075559-8, {N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} Acetamide, BRD-K97530723-001-07-6, BRD-K97530723-001-11-8, BRD-K97530723-001-19-1, BRD-K97530723-001-20-9, N -[2-(5-Methoxy-1 H -indol-3-yl)ethyl]acetamide;, F1929-1777, Melatonin, British Pharmacopoeia (BP) Reference Standard, Z1191880499, 0E2B08C1-B325-45B1-8939-6F9081EFDFA4, Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]- (6CI,8CI), Melatonin Working Standard (Secondary Reference Standard), Acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]- (9CI), Melatonin, United States Pharmacopeia (USP) Reference Standard, Melatonin, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C13H16N2O2
molecular_weight: 232.28 g/mol
exact_mass: 232.121177757 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 4
heavy_atom_count: 17
topological_polar_surface_area: 54.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Pale yellow leaflets from benzene
color: Pale yellow leaflets from benzene
solubility: In water, 2 g/L at 20 °C; 5 g/L at 50 °C
Descriptions:
{"pubchem": "Melatonin is a member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen atom is replaced by a 2-(5-methoxy-1H-indol-3-yl)ethyl group. It is a hormone secreted by the pineal gland in humans. It has a role as a geroprotector, a hormone, a central nervous system depressant, an anticonvulsant, a radical scavenger, an immunological adjuvant, a mouse metabolite and a human metabolite. It is a member of acetamides and a member of tryptamines. It is functionally related to a tryptamine.", "chebi": "A member of the class of  acetamides that is acetamide in which one of the hydrogens attached to the nitrogen atom is replaced by a 2-(5-methoxy-1<em>H</em>-indol-3-yl)ethyl group. It is a hormone secreted by the pineal gland in humans.", "chembl": "MELATONIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Melatonin, an indoleamine, is a natural compound produced by various organisms, including bacteria and eukaryotes. Its discovery in 1958 by Aaron B. Lerner and colleagues stemmed from the isolation of a substance from the pineal gland of cows that could induce skin lightening in common frogs. This compound was later identified as a hormone secreted in the brain during the night, playing a crucial role in regulating the sleep-wake cycle, also known as the circadian rhythm, in vertebrates.\nIn vertebrates, melatonin's functions extend to synchronizing sleep-wake cycles, encompassing sleep-wake timing and blood pressure regulation, as well as controlling seasonal rhythmicity (circannual cycle), which includes reproduction, fattening, molting, and hibernation. Its effects are mediated through the activation of melatonin receptors and its role as an antioxidant. In plants and bacteria, it serves as a defense mechanism against oxidative stress, indicating its evolutionary significance. Mitochondria, key organelles, are the main producers of melatonin, underscoring its \"ancient origins\" and its fundamental role in protecting the earliest cells from reactive oxygen species.\nIn addition to its endogenous functions as a hormone and antioxidant, melatonin is also administered exogenously as a dietary supplement and medication. Melatonin is used medically primarily for sleep-related problems: for example, prolonged-release melatonin (Circadin) is approved in several countries for short-term treatment of insomnia in people aged 55 years of age or older. It is used in the treatment of sleep disorders, including insomnia and various circadian rhythm sleep disorders.\n\n"}