680590-49-2

Basic information

• Product Name: EMPA
• Synonyms: N-Ethyl-2-[(6-methoxy-3-pyridinyl)[(2-methylphenyl)sulfonyl]amino]-N-(3-pyridinylmethyl)-acetamide;EMPA, CID 9981404
• CAS NO: 680590-49-2
• Molecular Formula: C₂₃H₂₆N₄O₄S
• Molecular Weight: 454.54194
• Product Categories: Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 680590-49-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 660.7±65.0 °C(Predicted)
• Appearance: white to light brown/
• Density: 1.280±0.06 g/cm3(Predicted)
• Storage Temp.: ?20°C
• PKA: 4.77±0.10(Predicted)
• CAS DataBase Reference: EMPA(CAS DataBase Reference)
• NIST Chemistry Reference: EMPA(680590-49-2)
• EPA Substance Registry System: EMPA(680590-49-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 680590-49-2(Hazardous Substances Data)

Usage

Description

EMPA is an orexin 2 receptor (OX2R) antagonist (Ki = 1.1 nM). It is selective for OX2R over OX1R (Ki = 900 nM). EMPA inhibits orexin-A- and orexin-B-induced calcium mobilization (IC50s = 8.8 and 7.9 nM, respectively) and increases orexin-A- and orexin-B-induced inositol phosphate accumulation (EC50s = 1.1 and 2.4 nM, respectively) in CHO(dHFr-) cells expressing recombinant human OX2R. It reduces spontaneous locomotor activity and orexin-B-induced hyperlocomotion in mice when administered at doses ranging between 10 and 300 mg/kg.

Upstream product

• 680591-13-3 N-(6-methoxypyridin-3-yl)-2-methylbenzenesulfonamide 
• 133-59-5 Toluene-2-sulfonyl chloride 
• 6628-77-9 6-methoxy-pyridin-3-ylamine 
• 1435913-07-7 C₂₂H₂₄N₄O₄S 
• 74-88-4 methyl iodide 
• 3000-75-7 N-ethyl-N-(3-pyridylmethyl)amine 
• 680591-44-0 [(6-methoxy-pyridin-3-yl)-(toluene-2-sulfonyl)-amino]-acetic acid 

Downstream Products

• 1435913-07-7 C₂₂H₂₄N₄O₄S 

Relevant articles and documents

Radiosynthesis and evaluation of [11C]EMPA as a potential PET tracer for orexin 2 receptors

EMPA is a selective antagonist of orexin 2 (OX2) receptors. Previous literature with [3H]-EMPA suggest that it may be used as an imaging agent for OX2 receptors; however, brain penetration is known to be modest. To evaluate the potential of EMPA as a PET radiotracer in non-human primate (as a step to imaging in man), we radiolabeled EMPA with carbon-11. Radiosynthesis of [11C]N-ethyl-2-(N-(6-methoxypyridin-3- yl)-2-methylphenylsulfonamido)-N-(pyridin-3-ylmethyl)acetamide ([ 11C]EMPA), and evaluation as a potential PET tracer for OX 2 receptors is described. Synthesis of an appropriate non-radioactive O-desmethyl precursor was achieved from EMPA with sodium iodide and chlorotrimethylsilane. Selective O-methylation using [11C]CH 3I in the presence of cesium carbonate in DMSO at room temp afforded [11C]EMPA in 1.5-2.5% yield (non-decay corrected relative to trapped [11C]CH3I at EOS) with ≥95% chemical and radiochemical purities. The total synthesis time was 34-36 min from EOB. Studies in rodent suggested that uptake in tissue was dominated by nonspecific binding. However, [11C]EMPA also showed poor uptake in both rats and baboon as measured with PET imaging.