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HomeProduct name listN-Ethylmaleimide

N-Ethylmaleimide

Synonym(s):NEM;N-Ethylmaleimide - CAS 128-53-0 - Calbiochem

  • CAS NO.:128-53-0
  • Empirical Formula: C6H7NO2
  • Molecular Weight: 125.13
  • MDL number: MFCD00005509
  • EINECS: 204-892-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-09 19:38:33
N-Ethylmaleimide Structural

What is N-Ethylmaleimide?

Chemical properties

White solid

The Uses of N-Ethylmaleimide

N-Ethylmaleimide is a protein thiol modifier which inhibits apoptotic DNA fragmentation. It is a sulfhydryl reagent and finds application in experimental biochemical studies as well as in enzymology. It is involved in the modification of cysteine residues in proteins and peptides. It acts as a Michael acceptor and reacts with nucelophiles like thiols. It is employed in the inhibition of Mg2+ dependent internucleosomal DNA fragmentation.

The Uses of N-Ethylmaleimide

Reagent for the covalent modification of cysteine residues in proteins. NEM gives a clear solution in ethanol at 50 mg/ml. NEM dissolves in water (>50 mg in 4 ml); however, aqueous solutions are unstable. The rate of hydrolysis is pseudo-first order and significantly dependent on pH.

The Uses of N-Ethylmaleimide

In cancer research (possible antimitotic activity.)

What are the applications of Application

N-Ethylmaleimide is a protein thiol modifier which inhibits apoptotic DNA fragmentation

Definition

ChEBI: N-ethylmaleimide is a member of the class of maleimides that is the N-ethyl derivative of maleimide. It has a role as an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor, an EC 2.7.1.1 (hexokinase) inhibitor, an EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor and an anticoronaviral agent. It is functionally related to a maleimide.

Hazard

Lachrymator when liquid, a strong irritant.

Biochem/physiol Actions

Augments currents from native M-channels in sympathetic neurons and acts as an opener for KCNQ2, KCNQ4 and KCNQ5 channels.

Safety Profile

Poison by intraperitoneal route. Human mutation data reported. Vapors are hlghly irritating. When heated to decomposition it emits toxic fumes of NOx.

Properties of N-Ethylmaleimide

Melting point: 43-46 °C(lit.)
Boiling point: 210 °C(lit.)
Density  1.2500 (rough estimate)
refractive index  1.4430 (estimate)
Flash point: 73 °C
storage temp.  2-8°C
solubility  methanol: 1 M at 20 °C, clear, colorless
form  Crystalline Powder
pka -2.18±0.20(Predicted)
color  White to off-white
Water Solubility  1 g/L (20 ºC)
Sensitive  Light Sensitive
Merck  14,3822
BRN  112448
Stability: Stable. Combustible. Incompatible with strong oxidizing agents. Refrigerate.
CAS DataBase Reference 128-53-0(CAS DataBase Reference)
NIST Chemistry Reference 1H-pyrrole-2,5-dione, 1-ethyl-(128-53-0)
EPA Substance Registry System N-Ethylmaleimide (128-53-0)

Safety information for N-Ethylmaleimide

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H300:Acute toxicity,oral
H311:Acute toxicity,dermal
H314:Skin corrosion/irritation
H317:Sensitisation, Skin
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

Computed Descriptors for N-Ethylmaleimide

InChIKey HDFGOPSGAURCEO-UHFFFAOYSA-N

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