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SML0209

Sigma-Aldrich

ANA-12

≥98% (HPLC)

Synonym(s):

N-[2-[[(Hexahydro-2-oxo-1H-azepin-3-yl)amino]carbonyl]phenyl]-benzo[b]thiophene-2-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C22H21N3O3S
CAS Number:
219766-25-3
Molecular Weight:
407.49
MDL number:
MFCD00117444
UNSPSC Code:
51111800
PubChem Substance ID:
329825231
NACRES:
NA.77

Quality Level

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

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
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Montalbano et al.
Hippocampus, 23(10), 879-889 (2013-05-16)
Long-term potentiation (LTP) is accompanied by increased spine density and dimensions triggered by signaling cascades involving activation of the neurotrophin brain-derived neurotrophic factor (BDNF) and cytoskeleton remodeling. Chemically-induced long-term potentiation (c-LTP) is a widely used cellular model of plasticity, whose
Agnieszka Pałucha-Poniewiera et al.
Behavioural pharmacology, 30(6), 471-477 (2019-02-07)
Ketamine has been shown to induce a rapid antidepressant effect on patients with depression. In many animal models, both rapid and sustained antidepressant activities were also found in response to an antagonist of group II metabotropic glutamate receptors, LY341495, and
Maxime Cazorla et al.
The Journal of clinical investigation, 121(5), 1846-1857 (2011-04-21)
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. However, therapeutic compounds that interact with TrkB receptors have been difficult
Valerie Jeanneret et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 38(11), 1896-1910 (2018-03-17)
Cerebral ischemia causes the presynaptic release of tissue-type plasminogen activator (tPA). The postsynaptic density (PSD) is a postsynaptic structure that provides a matrix where signaling transduction of excitatory synapses takes place. The postsynaptic density protein-95 (PSD-95) is the most abundant
Elizabeth T Barfield et al.
Frontiers in behavioral neuroscience, 11, 237-237 (2017-12-23)
Early-life trauma can increase the risk for, and severity of, several psychiatric illnesses. These include drug use disorders, and some correlations appear to be stronger in women. Understanding the long-term consequences of developmental stressor or stress hormone exposure and possible
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