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254940

Sigma-Aldrich

Methyl acetimidate hydrochloride

technical grade

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About This Item

Linear Formula:
CH3C(=NH)OCH3 · HCl
CAS Number:
14777-27-6
Molecular Weight:
109.55
Beilstein/REAXYS Number:
3671581
EC Number:
238-843-3
MDL number:
MFCD00012571
UNSPSC Code:
12352100
PubChem Substance ID:
24855275
NACRES:
NA.22

grade

technical grade

mp

105 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

Cl.COC(C)=N

InChI

1S/C3H7NO.ClH/c1-3(4)5-2;/h4H,1-2H3;1H

InChI key

WHYJXXISOUGFLJ-UHFFFAOYSA-N

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General description

Methyl acetimidate hydrochloride is an inhibitor of N-methylation of phosphatidylethanolamine. It also prevents the stimulation of purified cardiac sarcolemmal vesicles Ca2+-pump activities.

Application

Methyl acetimidate hydrochloride has been used in pre-crystallization chemical modification of lysine residues.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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T L Chao et al.
The Journal of biological chemistry, 256(11), 5324-5326 (1981-06-10)
The appearance of an immune response in some sickle cell anemia patients to reinfused autologous erythrocytes which had been treated with methyl acetimidate (Gabuzda, T. G., Chao, T. L., Berenfeld, M. R., and Gelbart, T. (1980) Blood 56, 1041--1047) was
T L Chao et al.
Hemoglobin, 5(1), 47-72 (1981-01-01)
The contribution of the high molecular weight hemoglobin (HMW Hb) to the antisickling effect produced by treatment of sickle cell erythrocytes with methyl acetimidate (MAI) was investigated. Erythrocytes obtained from sickle cell anemia and normal individuals were incubated with varying
P K Ganguly et al.
Biochemical and biophysical research communications, 130(1), 472-478 (1985-07-16)
Incubation of cardiac sarcoplasmic reticulum (SR) in the presence of S-adenosyl-L-methionine, a methyl donor for the enzymatic N-methylation of phosphatidylethanolamine, increased Ca2+-stimulated ATPase activity. The increase in Ca2+-ATPase activity was not due to changes in the affinity for Ca2+ and
V B Richardson et al.
Mutation research, 180(1), 121-129 (1987-09-01)
The cytogenetic effects of methyl acetimidate (MAI), a lysine-specific protein crosslinking reagent, were investigated using human peripheral lymphocytes in culture. Lymphocytes were treated with the chemical either prior to PHA exposure or 2-3 days following mitogenic stimulation and assessed for
G J van Scharrenburg et al.
Biochemistry, 23(25), 6285-6294 (1984-12-04)
To study the structural importance of the NH2-terminal Ala1 residue of pancreatic phospholipase A2, several mutants were prepared by a stepwise semisynthetic approach. 13C NMR spectroscopy of 90%-enriched [[3-13C]Ala1] phospholipases A2 shows the pK values of the alpha-NH3+ groups of
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