SML0209

ANA-12

≥98% (HPLC), TrkB antagonist, powder

• Synonym(s): N-[2-[[(Hexahydro-2-oxo-1H-azepin-3-yl)amino]carbonyl]phenyl]-benzo[b]thiophene-2-carboxamide
• Empirical Formula (Hill Notation): C₂₂H₂₁N₃O₃S
• CAS Number: 219766-25-3
• Molecular Weight: 407.49
• UNSPSC Code: 51111800
• PubChem Substance ID: 329825231
• NACRES: NA.77
• MDL number: MFCD00117444
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Product Name: ANA-12, ≥98% (HPLC)
• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: ≥5 mg/mL at 60 °C
• storage temp.: 2-8°C
• SMILES string: O=C1NCCCCC1NC(=O)c2ccccc2NC(=O)c3cc4ccccc4s3
• InChI: 1S/C22H21N3O3S/c26-20(25-17-10-5-6-12-23-21(17)27)15-8-2-3-9-16(15)24-22(28)19-13-14-7-1-4-11-18(14)29-19/h1-4,7-9,11,13,17H,5-6,10,12H2,(H,23,27)(H,24,28)(H,25,26)
• InChI key: TUSCYCAIGRVBMD-UHFFFAOYSA-N

Description

Application

ANA-12 was used to inhibit TrkB in primary mouse cortical neurons[1] and primary rat hippocampal cultures.[2]

Biochem/physiol Actions

The neurotrophin brain-derived neurotrophic factor (BDNF) and its receptor tropomyosin-related kinase B (TrkB) have emerged as key mediators in the pathophysiology of several mood disorders, including anxiety and depression. ANA-12 is a TrkB ligand that prevents activation of the receptor by BDNF with a high potency. It binds selectively to TrkB and inhibits processes downstream of TrkB without altering TrkA and TrkC functions. In adult mice model ANA-12 decreases TrkB activity in the brain without affecting neuronal survival. Mice dosed with ANA-12 show reduced anxiety- and depression related behaviors on a variety of tests predictive of anxiolytic and antidepressant properties in humans. ANA-12 may be a valuable tool for studying BDNF/TrkB signaling and may constitute a lead compound for developing the next generation of therapeutic agents for the treatment of mood disorders. There is also N-T19, which is less potent.

TrkB antagonist that possesses potent anxiolytic-like and antidepressant-like activities in mice

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable