B0753
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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All Photos(5)
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
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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)
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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)
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