Compound: Rimcazole
SMILES: N1(C[C@@H](N[C@@H](C1)C)C)CCCn2c3c(cccc3)c4c2cccc4
InChIKey: GUDVQJXODNJRIJ-CALCHBBNSA-N
Synonyms: Rimcazole, 75859-04-0, Rimcazol, BW-234U, Rimcazolum, BW 234U, C3N1PS8CX1, cis-9-(3-(3,5-dimethyl-1-piperazinyl)propyl)carbazole, DTXSID7048162, cis-9-[3-(3,5-dimethyl-1-piperazinyl)propyl]carbazole, RefChem:179466, DTXCID8028137, Rimcazole [INN], 9-[3-[(3S,5R)-3,5-dimethylpiperazin-1-yl]propyl]carbazole, CHEMBL275707, 9-[3-[(3R,5S)-3,5-dimethylpiperazin-1-yl]propyl]carbazole, 9-{3-[(3R,5S)-3,5-dimethylpiperazin-1-yl]propyl}-9H-carbazole, Rimcazol [INN-Spanish], Rimcazolum [INN-Latin], 207233-98-5, NCGC00025187-01, UNII-C3N1PS8CX1, Tocris-1497, 9-(3-(3,5-dimethylpiperazin-1-yl)propyl)-9H-carbazole, 9-[3-(3,5-Dimethyl-piperazin-1-yl)-propyl]-9H-carbazole, SCHEMBL99084, 9-[3-(3,5-dimethylpiperazin-1-yl)propyl]carbazole,hydrochloride, orb1702878, 9-[3-(3,5-Dimethyl-piperazin-1-yl)-propyl]-9H-carbazole(rimcazole), 9-[3-[cis-3,5-dimethylpiperazin-1-yl]propyl]carbazole, SCHEMBL29710924, CHEBI:94713, GUDVQJXODNJRIJ-CALCHBBNSA-N, GLXC-06496, 9H-Carbazole, 9-(3-(3,5-dimethyl-1-piperazinyl)propyl)-, cis-, EX-A5687, BDBM50019742, AKOS040746287, BR177827, DA-67207, HY-121813, CS-0083477, NS00121747, 9-[3-(3,5-cis-dimethylpiperazino)propyl]-carbazole, 9-[3-(3,5-cis-dimethylpiperazino)propyl]carbazole, Q7334422, 9-[3-(3,5-cis-dimethylpiperazino)-propyl]-carbazole, BRD-K70490179-300-01-2, 9-(3-(CIS-3,5-DIMETHYL-1-PIPERAZINYL)PROPYL)CARBAZOLE, 9-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propyl)-9H-carbazole, 9-[3-((3R,5R)-3,5-Dimethyl-piperazin-1-yl)-propyl]-9H-carbazole, 9-[3-((3R,5S)-3,5-Dimethyl-piperazin-1-yl)-propyl]-9H-carbazole, 9-[3-((3S,5R)-3,5-Dimethyl-piperazin-1-yl)-propyl]-9H-carbazole, 9-[3-(3,5-Dimethyl-piperazin-1-yl)-propyl]-9H-carbazole (Rimcazole) (BW234U), 9H-CARBAZOLE, 9-(3-((3R,5S)-3,5-DIMETHYL-1-PIPERAZINYL)PROPYL)-, REL-
Theoretical properties:
molecular_formula: C21H27N3
molecular_weight: 321.5 g/mol
exact_mass: 321.220497874 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 4
heavy_atom_count: 24
topological_polar_surface_area: 20.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 9-[3-[(3S,5R)-3,5-dimethyl-1-piperazinyl]propyl]carbazole is a member of carbazoles.
chembl: RIMCAZOLE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Rimcazole is an antagonist of the sigma receptor as well as a dopamine reuptake inhibitor. Sigma receptors are thought to be involved in the drug psychosis that can be induced by some drugs such as phencyclidine and cocaine, and rimcazole was originally researched as a potential antipsychotic with a different mechanism of action to traditional antipsychotic drugs, although common with butyrophenone antipsychotics such as haloperidol. Trials proved inconclusive and rimcazole was not pursued for this application, but other sigma antagonists continue to be researched for a variety of potential applications. Rimcazole has been shown to reduce the effects of cocaine, and analogues of rimcazole have been shown to be highly effective at blocking the convulsions caused by cocaine overdose in animal models. Isothiocyanate derivatives of rimcazole acting as irreversible dopamine transporter (DAT) blockers have been developed.