N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-hydroxy-6-methoxybenzamide

• ChemBase ID: 131139
• Molecular Formular: C15H22N2O3
• Molecular Mass: 278.34678
• Monoisotopic Mass: 278.16304257
• SMILES: CCN1CCC[C@H]1CNC(=O)c1c(cccc1OC)O
• Canonical SMILES: CCN1CCC[C@H]1CNC(=O)c1c(O)cccc1OC
• InChI: InChI=1S/C15H22N2O3/c1-3-17-9-5-6-11(17)10-16-15(19)14-12(18)7-4-8-13(14)20-2/h4,7-8,11,18H,3,5-6,9-10H2,1-2H3,(H,16,19)/t11-/m0/s1
• InChIKey: MVWKVVFFVMXULU-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-hydroxy-6-methoxybenzamide
• IUPAC Traditional name: N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-hydroxy-6-methoxybenzamide
• Synonyms: S(–)-2-Hydroxy-6-methoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide; S(-)-BZM; N-[[(2S)-1-Ethyl-2-pyrrolidinyl]methyl]-2-hydroxy-6-methoxybenzamide; (S)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-hydroxy-6-methoxybenzamide; S(-)-BZM

Database IDs

• CAS Number: 84226-04-0
• MDL Number: MFCD00210185
• PubChem SID: 162225417
• PubChem CID: 10956830

CALCULATED PROPERTIES

• Acid pKa: 7.9664807
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.73168844
• LogD (pH = 7.4): 0.96498984
• Log P: 1.3170981
• Molar Refractivity: 78.4561 cm^3
• Polarizability: 29.981123 Å^3
• Polar Surface Area: 61.8 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble5.6 mg/mL; DMSO: soluble14.6 mg/mL; ethanol: soluble24 mg/mL
• Apperance: pale yellow
• Optical Rotation: [α]22/D -78.5°, c = 0.57 in methylene chloride(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - B146

Application
Precursor to radio-iodinated S(–)-IBZM, a D2 dopamine receptor ligand.

Toronto Research Chemicals - B802800

A precursor to radio-iodinated S(–)-IBZM, a D2 dopamine receptor ligand.

REFERENCES

• Kung, H., et al.: J. Med. Chem., 31, 1039 (1988)
• Zea-Ponce, Y., et al.: Nucl. Med. Biol., 26, 661 (1988)
• Radau, P., et al.: J. Nucl. Med., 41, 220 (1988)