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B0753

Sigma-Aldrich

2,3-Butanedione monoxime

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

Synonym(s):

BDM, Biacetyl monoxime, Diacetyl monoxime

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About This Item

Linear Formula:
CH3C(=NOH)COCH3
CAS Number:
Molecular Weight:
101.10
Beilstein:
605582
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

2,3-Butanedione monoxime, ≥98%

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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