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SML0209

Sigma-Aldrich

ANA-12

≥98% (HPLC)

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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:
Molecular Weight:
407.49
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
SML0204SML2689SML0916
vibrant-m

SML0209

ANA-12

vibrant-m

SML0204

MS-1020

vibrant-m

SML2689

EN6

vibrant-m

SML0916

CaCCinh-A01

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

powder

form

powder

solubility

DMSO: ≥5 mg/mL at 60 °C

solubility

DMSO: ≥10 mg/mL at 60 °C

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

color

white to beige

color

white to tan

color

white to beige

color

white to beige

Application

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

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.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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