7-(acetyloxy)-1-methylquinolin-1-ium iodide

• ChemBase ID: 156701
• Molecular Formular: C12H12INO2
• Molecular Mass: 329.13365
• Monoisotopic Mass: 328.99127663
• SMILES: CC(=O)Oc1ccc2ccc[n+](c2c1)C.[I-]
• Canonical SMILES: CC(=O)Oc1ccc2c(c1)[n+](C)ccc2.[I-]
• InChI: InChI=1S/C12H12NO2.HI/c1-9(14)15-11-6-5-10-4-3-7-13(2)12(10)8-11;/h3-8H,1-2H3;1H/q+1;/p-1
• InChIKey: IFUAVRXVEJBLFI-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-(acetyloxy)-1-methylquinolin-1-ium iodide
• IUPAC Traditional name: 7-(acetyloxy)-1-methylquinolin-1-ium iodide
• Synonyms: AMQI; 7-Acetoxy-1-methylquinolinium iodide

Database IDs

• CAS Number: 7270-83-9
• MDL Number: MFCD00037374
• Beilstein Number: 4773437
• PubChem SID: 24845095; 162250838
• PubChem CID: 9883921

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -2.561656
• LogD (pH = 7.4): -2.561656
• Log P: -2.561656
• Molar Refractivity: 57.5166 cm^3
• Polarizability: 23.391178 Å^3
• Polar Surface Area: 30.18 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; H2O: soluble
• Melting Point: 222 °C(lit.)
• Fluorescence: λex 403 nm; λem 502 nm in 0.1 M Tris pH 8.0 (after cleavage by acetylcholin esterase)

Safety Information

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

Product Information

• Purity: ≥98.0% (HPCE)
• Grade: for fluorescence
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C12H12INO2

DETAILS

Sigma Aldrich - 00871

Other Notes
Fluorogenic substrate for cholinesterase3,4
Application
AMQI is a fluorescent substrate for acetylcholinesterase with λ excitation and λemission of 320 nm and 410 nm, respectively. Acetylcholinesterase hydrolyzes the fluorogenic substrate to form 7-hydroxy-1-methyl quinoliniom iodide with λ excitation and λ emission of 406 nm and 505 nm, respectively. It has been utilized in fluorometric assays to determine the bioactivity of this enzyme 1,2.