3,5-dichloro-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-hydroxy-6-methoxybenzamide hydrochloride

• ChemBase ID: 177238
• Molecular Formular: C15H21Cl3N2O3
• Molecular Mass: 383.69784
• Monoisotopic Mass: 382.06177558
• SMILES: C1C[C@H](N(C1)CC)CNC(=O)c1c(c(cc(c1O)Cl)Cl)OC.Cl
• Canonical SMILES: CCN1CCC[C@H]1CNC(=O)c1c(O)c(Cl)cc(c1OC)Cl.Cl
• InChI: InChI=1S/C15H20Cl2N2O3.ClH/c1-3-19-6-4-5-9(19)8-18-15(21)12-13(20)10(16)7-11(17)14(12)22-2;/h7,9,20H,3-6,8H2,1-2H3,(H,18,21);1H/t9-;/m0./s1
• InChIKey: ITLUETSTZABOFM-FVGYRXGTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-dichloro-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-hydroxy-6-methoxybenzamide hydrochloride
• IUPAC Traditional name: raclopride hydrochloride
• Synonyms: 3,5-Dichloro-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2-hydroxy-6-methoxybenzamide Hydrochloride; (-)-Raclopride Hydrochloride; FLA 870; Raclopride Hydrochloride

Database IDs

• CAS Number: 98527-32-3
• PubChem SID: 164233148
• PubChem CID: 54752790

CALCULATED PROPERTIES

• Acid pKa: 6.259372
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.2700703
• LogD (pH = 7.4): 2.0286963
• Log P: 2.004544
• Molar Refractivity: 88.0657 cm^3
• Polarizability: 33.83828 Å^3
• Polar Surface Area: 61.8 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R070800

A dopamine receptor as potential neuroleptic agent.

REFERENCES

• Gevins, A., et al.: Science, 235, 580 (1987)
• Volkow, N., et al.: J. Nucl. Med., 36, 2162 (1987)
• Bray, C., et al.: J. Investig. Med., 52, 192 (1987)
• Deadwyler, S., et al.: J. Neurosci., 27, 14239 (1987)