N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-hydroxy-3-iodo-6-methoxybenzamide

• ChemBase ID: 132179
• Molecular Formular: C15H21IN2O3
• Molecular Mass: 404.24331
• Monoisotopic Mass: 404.05969054
• SMILES: CCN1CCC[C@H]1CNC(=O)c1c(ccc(c1O)I)OC
• Canonical SMILES: CCN1CCC[C@H]1CNC(=O)c1c(OC)ccc(c1O)I
• InChI: InChI=1S/C15H21IN2O3/c1-3-18-8-4-5-10(18)9-17-15(20)13-12(21-2)7-6-11(16)14(13)19/h6-7,10,19H,3-5,8-9H2,1-2H3,(H,17,20)/t10-/m0/s1
• InChIKey: CANPFCFJURGKAX-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-hydroxy-3-iodo-6-methoxybenzamide
• IUPAC Traditional name: iodobenzamide
• Synonyms: (S)-(-)-3-Iodo-2-hydroxy-6-methoxy-N[(1-ethyl-2-pyrrolidinyl)methyl]benzamide; Iodobenzamide; (S)-(-)-IBZM; N-[[(2S)-1-Ethyl-2-pyrrolidinyl]methyl]-2-hydroxy-3-iodo-6-methoxybenzamide; (S)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-hydroxy-3-iodo-6-methoxybenzamide; IBZM

Database IDs

• CAS Number: 130383-75-4; 84226-06-2
• MDL Number: MFCD00210201
• PubChem SID: 162226456
• PubChem CID: 107995

CALCULATED PROPERTIES

• Acid pKa: 7.0490904
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.4690014
• LogD (pH = 7.4): 1.8044207
• Log P: 1.849388
• Molar Refractivity: 91.8186 cm^3
• Polarizability: 35.158455 Å^3
• Polar Surface Area: 61.8 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble49.3 mg/mL; ethanol: soluble8 mg/mL; H2O: slightly soluble <0.5 mg/mL
• Apperance: dark yellow
• Optical Rotation: [α]22/D -68.5°, c = 0.63 in methylene chloride(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - I139

Biochem/physiol Actions
D2 dopamine receptor antagonist.
Caution
Hygroscopic, photosensitive

Toronto Research Chemicals - I163500

A halogenated benzamide derivative as potential radioligands for non-invasive quantification of D2-like dopamine receptor. The main purpose of a brain study with IBZM is the differentiation of Parkinson’s disease from other neurodegenerative diseases like

REFERENCES

• Chumpradit, S., et al.: J. Med. Chem., 36, 221 (1993)
• Schmidt, D., et al.: J. Pharm. Sci., 83, 305 (1993)
• Sandell, J., et al.: J. Labelled Compd. Radiopharm., 43, 331 (1993)
• Siessmeier, T., et al.: J. Nucl. Med., 46, 964 (1993)
• Stark, D., et al.: Bioo