SB 224289
Basic information
- CAS
180083-23-2- Standard SMILES
Cc1nc(-c2ccc(-c3ccc(C(=O)N4CCc5cc6c(cc54)C4(CCN(C)CC4)CO6)cc3)c(C)c2)no1- InChIKey
ATQMRMGXINTJHV-UHFFFAOYSA-N- Molecular formula
- C32H32N4O3
- Average molar mass
- 520.6 g/mol
- Monoisotopic mass
- 520.2474409
Overview
SB 224289 is a member of the class of benzamides obtained by formal condensation of the carboxy group of 2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid with the secondary amino group of 1'-methyl-6,7-dihydro-5H-spiro[furo[2,3-f]indole-3,4'-piperidine]. Selective 5-HT1B receptor antagonist (pKi = 8.2). Displays >60-fold selectivity over 5-HT1D, 5-HT1A, 5-HT1E, 5-HT1F, 5-HT2A and 5-HT2C receptors in radioligand binding and functional assays. Centrally active following oral administration in vivo. It has a role as a serotonergic antagonist. It is a member of benzamides, an azaspiro compound, an organic heterotetracyclic compound and a 1,2,4-oxadiazole. It is a conjugate base of a SB 224289(1+).
Names & identifiers
- Preferred name
- SB 224289
- IUPAC
- [4-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]phenyl]-(1'-methylspiro[6,7-dihydro-2H-furo[2,3-f]indole-3,4'-piperidine]-5-yl)methanone
- English name
- 1'-Methyl-5-[[2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole]-3,4'-piperidine hydrochloride
- Molecular formula
- C32H32N4O3
- Molecular weight
- 520.62
Names & synonyms
180083-23-2SB 224289SB-224289(2'-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)(1'-methyl-6,7-dihydrospiro[furo[2,3-f]indole-3,4'-piperidin]-5(2H)-yl)methanoneSB224289J854.001BF95C648W4N(1'-Methyl-6,7-dihydro-5H-spiro(furo(2,3-f)indole-3,4'-piperidin)-5-yl)(2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methanoneDTXSID4043987CHEBI:64069(2'-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)-(1,1'-biphenyl)-4-yl)(1'-methyl-6,7-dihydrospiro(furo(2,3-f)indole-3,4'-piperidin)-5(2H)-yl)methanone(4-(2-Methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)phenyl)-(1'-methylspiro(6,7-dihydro-2H-furo(2,3-f)indole-3,4'-piperidine)-5-yl)methanone
Show more names
CS-2436SB224289HClSB 224,289 HYDROCHLORIDE(2'-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)(1'-methyl-6,7-dihydrospiro(2'-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)(1'-methyl-6,7-dihydrospiro[fu
Properties
Computed structural properties
- XLogP
- 5.6
- Topological polar surface area
- 71.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 39
- Formal charge
- 0
- Complexity
- 885
Physicochemical properties
- Melting point
- 280 ℃ · >280℃
- Boiling point
- 724.8 · 724.8±70.0 °C(Predicted)
- Density
- 1.34 · 1.34
- storage temp.
- Store at RT
- solubility
- 4.5 mg/mL · DMSO: 4.5 mg/mL
- form
- solid
- pka
- 9.85 · 9.85±0.20(Predicted)
- color
- off-white
- FDA UNII
- 95 C648W4N · F95C648W4N
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- safety_code
- 22-24/25
Chemistry & industry
Applications
UsesSB 224289A is a 5-HT1B antagonist and a useful compound to examine the role of 5-HT1B receptors in cocaine self-administration and cocaine-seeking behavior (1,2).
Additional notes
DefinitionChEBI: SB 224289 is a member of the class of benzamides obtained by formal condensation of the carboxy group of 2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid with the secondary amino group of 1'-methyl-6,7-dihydro-5H-spiro[furo[2,3-f]indole-3,4'-piperidine]. Selective 5-HT1B receptor antagonist (pKi = 8.2). Displays >60-fold selectivity over 5-HT1D, 5-HT1A, 5-HT1E, 5-HT1F, 5-HT2A and 5-HT2C receptors in radioligand binding and functional assays. Centrally active following oral administration in vivo. It has a role as a serotonergic antagonist. It is an organic heterotetracyclic compound, an azaspiro compound, a 1,2,4-oxadiazole and a member of benzamides. It is a conjugate base of a SB 224289(1+).
Related reactions
1 records
Compound notes
Loading…