N-[2-(6-chloro-5-methoxy-1H-indol-3-yl)ethyl]acetamide

• ChemBase ID: 105314
• Molecular Formular: C13H15ClN2O2
• Molecular Mass: 266.7234
• Monoisotopic Mass: 266.08220541
• SMILES: COc1cc2c([nH]cc2CCNC(=O)C)cc1Cl
• Canonical SMILES: COc1cc2c(CCNC(=O)C)c[nH]c2cc1Cl
• InChI: InChI=1S/C13H15ClN2O2/c1-8(17)15-4-3-9-7-16-12-6-11(14)13(18-2)5-10(9)12/h5-7,16H,3-4H2,1-2H3,(H,15,17)
• InChIKey: LUINDDOUWHRIPW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(6-chloro-5-methoxy-1H-indol-3-yl)ethyl]acetamide
• IUPAC Traditional name: N-[2-(6-chloro-5-methoxy-1H-indol-3-yl)ethyl]acetamide
• Synonyms: 6-CHLOROMELATONIN; N-Acetyl-6-chloro-5-methoxytryptamine; 6-Chloromelatonin; N-乙酰基-6-氯-5-甲氧基色胺; 6-氯褪黑激素

Database IDs

• CAS Number: 63762-74-3
• MDL Number: MFCD00209923
• PubChem SID: 162092102
• PubChem CID: 1858

CALCULATED PROPERTIES

• Acid pKa: 14.920186
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.7516572
• LogD (pH = 7.4): 1.7516575
• Log P: 1.7516575
• Molar Refractivity: 71.0847 cm^3
• Polarizability: 28.5054 Å^3
• Polar Surface Area: 54.12 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: alcohol: soluble

Safety Information

• Storage Condition: 2-8°C, Desiccate
• RTECS: AB5750000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-23/24/25-36/37/38
• Safety Statements: 53-26-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335-H360
• GHS Precautionary statements: P201-P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... MTNR1A(4543), MTNR1B(4544)

Product Information

• Empirical Formula (Hill Notation): C13H15ClN2O2

DETAILS

MP Biomedicals - 02159748

Inhibits calcium-dependent dopamine release.

Sigma Aldrich - C0331

Biochem/physiol Actions
Melatonin agonist active at nanomolar concentrations; binds more strongly than melatonin at the receptor. Also has binding sites outside the CNS, i.e., at the adrenal gland. Possesses antiproliferative activity.