B0753

2,3-Butanedione monoxime

≥98% (GC), powder, ATP-sensitive K⁺ and Ca²⁺ channel inhibitor

• Synonym(s): BDM, Biacetyl monoxime, Diacetyl monoxime
• Linear Formula: CH₃C(=NOH)COCH₃
• CAS Number: 57-71-6
• Molecular Weight: 101.10
• Beilstein/REAXYS Number: 605582
• EC Number: 200-348-5
• MDL number: MFCD00002116
• UNSPSC Code: 12352200
• PubChem Substance ID: 57653910
• NACRES: NA.77

Properties

• Product Name: 2,3-Butanedione monoxime, ≥98%
• assay: ≥98%
• form: powder
• bp: 185-186 °C (lit.)
• mp: 75-78 °C (lit.)
• SMILES string: CC(=O)\C(C)=N\O
• InChI: 1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3/b5-3+
• InChI key: FSEUPUDHEBLWJY-HWKANZROSA-N
• Gene Information: human ... KCNB1(3745)

Description

Application

2,3-Butanedione monoxime has been used:

• in single-molecule myosin V motility assays
• as an anesthetic in the approach of imaging transgenic animals
• to reduce rigor tension in muscle fibres
• as a media component for mice cardiomyocytes culture

Biochem/physiol Actions

2,3-Butanedione monoxime is inhibitor of ATP-sensitive K⁺ and Ca²⁺ channels.

DRK1 is a delayed rectifier (Kv2.1) cloned K⁺ channel from rat brain with consensus sites for protein kinase-dependent phosphorylation that might be expected to be functionally regulated by phosphorylation. 2,3-Butanedione monoxime (BDM) chemically removes phosphate groups from many proteins, and its action on DRK1 channels was examined after expression of DRK1 cRNA in Xenopus oocytes. In two-microelectrode voltage-clamp experiments, the application of 2,3-Butanedione monoxime to the bath inhibited DRK1 current (ki = 16.6 mM, H = 0.96) rapidly and reversibly, with a time course similar to the time course of solution change within the bath. DRK1 current was inhibited at all potentials; the time course of current activation, deactivation and inactivation were unaffected by 2,3-Butanedione monoxime. In inside-out patch-clamp experiments, the application of 2,3-Butanedione monoxime to the cytoplasmic surface similarly inhibited channel activity rapidly and reversibly (ki = 10.7 mM, H = 1.01) in the absence of rephosphorylating substrates. These results are inconsistent with a phosphatase effect, because such an effect should be irreversible in cell-free, ATP-free patches. Instead, the results suggest that 2,3-Butanedione monoxime can inhibit DRK1 channels directly from inside or outside of the membrane.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)