N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide

• ChemBase ID: 72589
• Molecular Formular: C15H17NO2
• Molecular Mass: 243.30098
• Monoisotopic Mass: 243.12592879
• SMILES: C(=O)(C)NCCc1cccc2ccc(cc12)OC
• Canonical SMILES: COc1ccc2c(c1)c(CCNC(=O)C)ccc2
• InChI: InChI=1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17)
• InChIKey: YJYPHIXNFHFHND-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
• IUPAC Traditional name: agomelatine
• Synonyms: N-[2-(7-Methoxy-1-naphthalenyl)ethyl]-acetamide; S-20098; Agomelatine; N-(2-(7-methoxynaphthalen-1-yl)ethyl)acetamide; N-[2-(7-Methoxy-1-naphthalenyl)ethyl]acetamide; N-[2-(7-Methoxy-1-naphthyl)ethyl]acetamide; S 20098; Valdoxan; Melitor; Thymanax; Agomelatine

Database IDs

• CAS Number: 138112-76-2
• MDL Number: MFCD00916659
• PubChem SID: 162037514
• PubChem CID: 82148

CALCULATED PROPERTIES

• Acid pKa: 15.964533
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.0383275
• LogD (pH = 7.4): 2.0383275
• Log P: 2.0383275
• Molar Refractivity: 71.6436 cm^3
• Polarizability: 28.953741 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: >50 mg/mL; Methanol
• Apperance: White Solid; white to off-white powder
• Melting Point: 107-109°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• European Hazard Symbols: Nature polluting (N)
• German water hazard class: 3
• Risk Statements: 50
• Safety Statements: 61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: 5-HT receptor

Product Information

• Purity: ≥98% (HPLC); 95+%; 97%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H17NO2

DETAILS

Selleck Chemicals - S1243

Research Area: Depressive disorders
Biological Activity:
Agomelatine is an antidepressant drug. It is classified as a norepinephrine-dopamine disinhibitor (NDDI) due to its antagonism of the 5-HT2C receptor. Activation of 5-HT2C receptors by serotonin inhibits dopamine and norepinephrine release. Antagonism of 5-HT2C results in an enhancement of DA and NE release and activity of frontocortical dopaminergic and adrenergic pathways. [1]Agomelatine is also a potent agonist at melatonin receptors which makes it the first melatonergic antidepressant. [2]References on Agomelatine[1] http://en.wikipedia.org/wiki/Agomelatine, , [2] Research Journal of Pharmaceutical, Biological and Chemical Sciences, ,

Sigma Aldrich - A1362

Biochem/physiol Actions
Agomelatine is an extremely potent agonist at both melatonin receptors (MT1 and MT2), with additional antagonism at 5HT2C. It is a novel antidepressant with many desired in vivo properties, including neuroprotection and neurogenesis in depression-sensitive brain areas. Agomelatine′s efficacy appears to be due to both melatonergic and serotonergic properties. In neurogenesis assays, both in vitro and in vivo, the compound effects were differentially affected by antagonists for MT1/MT2 and 5HT2C, demonstrating actions through all three receptors.

Toronto Research Chemicals - A430000

Agomelatine is a melatoninergic agonist and selective antagonist of 5-HT2C receptors, and has been shown to be active in several animal models of depression. Agomelatine (S20098) displayed pKi values of 6.4 and 6.2 at native (porcine) and cloned, human

REFERENCES

• http://en.wikipedia.org/wiki/Agomelatine
• Yous, S., et al.: J. Med. Chem., 35, 1484 (1992)
• Zhdanova, I., et al.: J. Clin. Endocrinol. Metab., 86, 4727 (1992)
• Cajochen, C., et al.: J. Pineal Res., 35, 149 (1992)