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B0753

Sigma-Aldrich

2,3-Butanedione monoxime

≥98%

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Synonym(s):
BDM, Biacetyl monoxime, Diacetyl monoxime
Linear Formula:
CH3C(=NOH)COCH3
CAS Number:
Molecular Weight:
101.10
Beilstein/REAXYS Number:
605582
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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)

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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.

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)


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