Compound: Coluracetam
SMILES: O=C1N(CCC1)CC(=O)Nc2c3c(nc4c2c(c(C)o4)C)CCCC3
InChIKey: PSPGQHXMUKWNDI-UHFFFAOYSA-N
Synonyms: Coluracetam, 135463-81-9, N-(2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-yl)-2-(2-oxopyrrolidin-1-yl)acetamide, bci-540, Coluracetam [INN], UNII-V6FL6O5GR7, MKC 231, DTXSID60159386, N-(2,3-Dimethyl-5,6,7,8-tetrahydrofuro(2,3-b)quinolin-4-yl)-2-(2-oxopyrrolidin-1-yl)acetamide, 1-Pyrrolidineacetamide, 2-oxo-N-(5,6,7,8-tetrahydro-2,3-dimethylfuro(2,3-b)quinolin-4-yl)-, coluracetamum, RefChem:127557, DTXCID7081877, MKC-231, MFCD00901416, V6FL6O5GR7, 2-(2-Oxypyrrolidin-1-yl)-N-(2,3-dimethyl-5,6,7,8-tetrahydrofuro(2,3-b)quinolin-4-yl)acetoamide, N-{2,3-DIMETHYL-5H,6H,7H,8H-FURO[2,3-B]QUINOLIN-4-YL}-2-(2-OXOPYRROLIDIN-1-YL)ACETAMIDE, Coluracetam (Standard), CHEMBL37935, SCHEMBL194780, orb1299680, EX-A739, Coluracetam;MKC-231;BCI-540, GLXC-04497, HMS3886I15, HMS5084L15, HY-17553R, s5222, AKOS015842255, CCG-267931, NCGC00378715-01, AC-31948, DS-14004, HY-17553, SY111873, DB-361033, C3689, NS00067957, Q3683872, BRD-K23672206-001-01-4, N-(2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-yl)-2-(2-oxo-1-pyrrolidinyl)acetamide, N-(2,3-Dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-yl)-2-(2-oxopyrroli din-1-yl)acetamide
Theoretical properties:
molecular_formula: C19H23N3O3
molecular_weight: 341.4 g/mol
exact_mass: 341.17394160 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 3
heavy_atom_count: 25
topological_polar_surface_area: 75.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: COLURACETAM is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Coluracetam (INN; development code BCI-540; formerly MKC-231) is a purported nootropic agent of the racetam family.  It contains a chemical group that is a bioisostere of the 9-amino-tetrahydroacridine family. It was initially developed and tested by the Mitsubishi Tanabe Pharma Corporation for Alzheimer's disease. After the drug failed to reach endpoints in its clinical trials it was in-licensed by BrainCells Inc for investigations into major depressive disorder (MDD), which was preceded by being awarded a "Qualifying Therapeutic Discovery Program Grant" by the state of California. Findings from phase IIa clinical trials have suggested that it would be a potential medication for comorbid MDD with generalized anxiety disorder (GAD).  BrainCells Inc is currently out-licensing the drug for this purpose. It may also have potential use in prevention and treatment of ischemic retinopathy and retinal and optic nerve injury.
Coluracetam has been shown to reverse the loss of choline acetyltransferase production in the medial septal nucleus of rats exposed to phencyclidine (PCP), and is considered a potential therapeutic drug for schizophrenia.
The drug has been sold online as a nootropic. It is anecdotally claimed to produce visual effects such as improved color, slight synaesthesia, and an "HD visual effect", analogously to sub-hallucinogenic dose of the serotonergic psychedelic psilocybin. Other purported effects include enhanced mood and reduced anxiety.