4-amino-N-{1-azabicyclo[2.2.2]octan-3-yl}-5-chloro-2-methoxybenzamide hydrate hydrochloride

• ChemBase ID: 155054
• Molecular Formular: C15H23Cl2N3O3
• Molecular Mass: 364.26742
• Monoisotopic Mass: 363.11164697
• SMILES: COc1c(cc(c(c1)N)Cl)C(=O)NC1[C@H]2CCN(C1)CC2.O.Cl
• Canonical SMILES: COc1cc(N)c(cc1C(=O)NC1CN2CC[C@H]1CC2)Cl.O.Cl
• InChI: InChI=1S/C15H20ClN3O2.ClH.H2O/c1-21-14-7-12(17)11(16)6-10(14)15(20)18-13-8-19-4-2-9(13)3-5-19;;/h6-7,9,13H,2-5,8,17H2,1H3,(H,18,20);1H;1H2
• InChIKey: NPXXKMBXEODDAF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-{1-azabicyclo[2.2.2]octan-3-yl}-5-chloro-2-methoxybenzamide hydrate hydrochloride
• IUPAC Traditional name: zacopride hydrate hydrochloride
• Synonyms: 4-Amino-N-1-azabicyclo[2.2.2]oct-3-yl-5-chloro-2-methoxybenzamide hydrochloride hydrate; Zacopride hydrochloride hydrate

Database IDs

• CAS Number: 101303-98-4(anhydrous)
• MDL Number: MFCD20488057
• PubChem SID: 162249192
• PubChem CID: 19849157

CALCULATED PROPERTIES

• Acid pKa: 14.591333
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.2240837
• LogD (pH = 7.4): 0.5038138
• Log P: 1.0406586
• Molar Refractivity: 83.9718 cm^3
• Polarizability: 31.678123 Å^3
• Polar Surface Area: 67.59 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥10 mg/mL
• Apperance: white to tan powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H20ClN3O2 · HCl · xH2O

DETAILS

Sigma Aldrich - SML0081

Biochem/physiol Actions
Zacopride is a sub-nanomolar antagonist of the serotonin 5-HT3 receptor that also displays agonist-like activity against 5-HT4 receptors. It is a potent anxiolytic in animal models, and also has strong antiemetic effects, and also increases aldosterone levels via activation of 5-HT4 receptor in the adrenal glands.