Compound: NSI-189
SMILES: O=C(N1CCN(Cc2ccccc2)CC1)c3c(nccc3)NCCC(C)C
InChIKey: DYTOQURYRYYNOR-UHFFFAOYSA-N
Synonyms: NSI-189, 1270138-40-3, YVE9U408ZL, Methanone, [2-[(3-methylbutyl)amino]-3-pyridinyl][4-(phenylmethyl)-1-piperazinyl]-, Methanone, (2-((3-methylbutyl)amino)-3-pyridinyl)(4-(phenylmethyl)-1-piperazinyl)-, (2-((3-Methylbutyl)amino)-3-pyridinyl)(4-(phenylmethyl)-1-piperazinyl)methanone, [2-[(3-Methylbutyl)amino]-3-pyridinyl][4-(phenylmethyl)-1-piperazinyl]methanone, RefChem:854938, (4-benzylpiperazin-1-yl)(2-(isopentylamino)pyridin-3-yl)methanone, (4-benzylpiperazin-1-yl)-[2-(3-methylbutylamino)pyridin-3-yl]methanone, MFCD26959792, (4-benzylpiperazin-1-yl)-[2-(isopentylamino)-3-pyridyl]methanone, UNII-YVE9U408ZL, (2-((3-Methylbutyl)amino)-3-pyridinyl)(4-(phenylmethyl)-1-piperazinyl)-methanone, Amdiglurax, [2-[(3-methylbutyl)amino]-3-pyridinyl][4-(phenylmethyl)-1-piperazinyl]-Methanone, amdiglurax [INN], orb1307355, SCHEMBL9999791, CHEMBL4302505, SCHEMBL29766917, EX-A277, CHEBI:228696, BDBM655802, DTXSID901025668, GLXC-90086, HMS3886A14, NSI-189?, s5620, (4-benzylpiperazin-1-yl)(2-(isopentylamino)pyridin-3-yl)methanone (NSI-189), AKOS025395148, CCG-268247, CS-2029, SB17520, US20240067625, Compound 29, NCGC00371142-05, AC-31950, AS-19608, DA-46482, FN138081, HY-13999, SY241812, NS00098469, BRD-K74371986-001-01-7, Q15409359, (4-Benzyl-1-piperazinyl)[2-(isopentylamino)-3-pyridyl]methanone, NSI-189 ((4-benzylpiperazin-1-yl)-[2-(3-methylbutylamino)pyridin-3-yl]methanone)
Theoretical properties:
molecular_formula: C22H30N4O
molecular_weight: 366.5 g/mol
exact_mass: 366.24196159 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 7
heavy_atom_count: 27
topological_polar_surface_area: 48.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: NSI-189 is a pyridinemonocarboxylic acid and an aromatic carboxylic acid.
chembl: NSI-189 is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Amdiglurax (INNTooltip International Nonproprietary Name), also known by its former developmental code names ALTO-100 and NSI-189 (short for "NeuralStem Inc. 189"), is a drug described as a hippocampal neurogenesis stimulant and indirect brain-derived neurotrophic factor (BDNF) modulator which is under development for the treatment of major depressive disorder (MDD), bipolar depression, and post-traumatic stress disorder (PTSD). There has also been interest in amdiglurax for possible treatment of cognitive impairment and neurodegeneration. It is taken by mouth.
Amdiglurax's exact mechanism of action is unknown. However, it is thought to work through indirectly enhancing BDNF signaling and increasing neuroplasticity and neurogenesis in the hippocampus. The drug dose-dependently increases hippocampal volume at sufficiently high doses in rodents. However, it did not significantly affect hippocampal volume in humans in a clinical study. Amdiglurax is a first-in-class drug and a small molecule.
As of July 2024, amdiglurax is in phase 2 clinical trials for MDD, bipolar depression, and PTSD. A phase 3 trial for MDD is being planned. Findings of the effectiveness of amdiglurax in treating MDD in phase 1 and 2 trials have been mixed, although cognitive and memory improvements have been observed. Amdiglurax is under development by Alto Neuroscience and was previously under development by Neuralstem, Inc. It has been sold online as a nootropic and antidepressant.