N-[(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-3-(propan-2-yl)-2,3-dihydro-1H-1,3-benzodiazole-1-carboxamide hydrate hydrochloride

• ChemBase ID: 154634
• Molecular Formular: C19H29ClN4O3
• Molecular Mass: 396.91156
• Monoisotopic Mass: 396.19281849
• SMILES: CC(C)n1c2ccccc2n(c1=O)C(=O)N[C@H]1C[C@H]2CC[C@@H](C1)N2C.O.Cl
• Canonical SMILES: CN1[C@@H]2CC[C@H]1C[C@H](C2)NC(=O)n1c(=O)n(c2c1cccc2)C(C)C.O.Cl
• InChI: InChI=1S/C19H26N4O2.ClH.H2O/c1-12(2)22-16-6-4-5-7-17(16)23(19(22)25)18(24)20-13-10-14-8-9-15(11-13)21(14)3;;/h4-7,12-15H,8-11H2,1-3H3,(H,20,24);1H;1H2/t13-,14+,15-
• InChIKey: HZJJVFOOACXPTH-XZAJHMFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-3-(propan-2-yl)-2,3-dihydro-1H-1,3-benzodiazole-1-carboxamide hydrate hydrochloride
• IUPAC Traditional name: 3-isopropyl-N-[(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-1,3-benzodiazole-1-carboxamide hydrate hydrochloride
• Synonyms: 2,3-Dihydro-N-[(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]-3-(1-methylethyl)-2-oxo-1H-benzimidazole-1-carboxamide Hydrochloride (1:1) hydrate; BIMU8 hydrate

Database IDs

• CAS Number: 134296-40-5(anhydrous)
• PubChem SID: 162248772
• PubChem CID: 71311918

CALCULATED PROPERTIES

• Acid pKa: 15.286645
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.435694
• LogD (pH = 7.4): 0.05255055
• Log P: 1.854125
• Molar Refractivity: 95.9691 cm^3
• Polarizability: 37.13273 Å^3
• Polar Surface Area: 55.89 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥5 mg/mL
• Apperance: off-white to light tan

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H26N4O2·HCl · xH2O

DETAILS

Sigma Aldrich - B4063

Biochem/physiol Actions
BIMU8 hydrate is a potent 5-HT4 serotonin receptor agonist. Serotonin (5-HT) is a major neurotransmitter that acts through a family of GPCRs and one ion channel. 5-HT4 receptor is GPCR expressed in many tissues, including brain, and modulates dopamine secretion, learning, and memory. BIMU8 is a full agonist at 5-HT4, but it binds differently than the endogenous ligand, 5-HT, shown through site-directed mutagenesis studies. It depolarizes neurons and was used to localize 5-HT4 to somatic but not dendritic regions of CA1 pyramidal neurons.