2-[2-(hydroxymethyl)-5-nitro-1H-imidazol-1-yl]ethan-1-ol

• ChemBase ID: 127759
• Molecular Formular: C6H9N3O4
• Molecular Mass: 187.15336
• Monoisotopic Mass: 187.05930578
• SMILES: c1c(n(c(n1)CO)CCO)[N+](=O)[O-]
• Canonical SMILES: OCCn1c(CO)ncc1[N+](=O)[O-]
• InChI: InChI=1S/C6H9N3O4/c10-2-1-8-5(4-11)7-3-6(8)9(12)13/h3,10-11H,1-2,4H2
• InChIKey: AEHPOYAOLCAMIU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(hydroxymethyl)-5-nitro-1H-imidazol-1-yl]ethan-1-ol
• IUPAC Traditional name: hydroxymetronidazole
• Synonyms: Metronidazole-OH; 1-(2-Hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole; Hydroxymetronidazole; MNZOH; Hydroxymetronidazole; Metronidazole-OH; 2-(Hydroxymethyl)-5-nitro-1H-imidazole-1-ethanol; 1-(2-Hydroxyethyl)-2-(hydroxymethyl)-5-nitroimidazole; Hydroxy Metronidazole; 1-(2-羟乙基)-2-羟甲基-5-硝基咪唑; 羟基甲硝唑; 羟基甲硝唑

Database IDs

• CAS Number: 4812-40-2
• MDL Number: MFCD01721480
• PubChem SID: 24860767; 162222077
• PubChem CID: 121858
• Chemspider ID: 108713
• Wikipedia Title: Hydroxymetronidazole

CALCULATED PROPERTIES

• Acid pKa: 13.817862
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.276603
• LogD (pH = 7.4): -1.276559
• Log P: -1.2765583
• Molar Refractivity: 42.9227 cm^3
• Polarizability: 15.946683 Å^3
• Polar Surface Area: 104.1 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 118-121°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: NI5568000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C6H9N3O4

DETAILS

Sigma Aldrich - 34007

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - H948395

A metabolite of Metronidazole (M338880).

REFERENCES

• Haller, I., et al.: Antimicrob. Agents Chemother., 22, 165 (1982)
• Gibson, R., et al.: Clin. Chem., 30, 784 (1982)
• Kuti, J., et al.: Pharmacotherapy, 25, 935 (1982)