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Merck
CN

M1777

N-Methyl-1-deoxynojirimycin

≥98%

Synonym(s):

1,5-Dideoxy-1,5-imino-1-methyl-D-sorbitol

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About This Item

Empirical Formula (Hill Notation):
C7H15NO4
CAS Number:
69567-10-8
Molecular Weight:
177.20
UNSPSC Code:
51102829
NACRES:
NA.32
PubChem Substance ID:
24896690
MDL number:
MFCD00133609
Beilstein/REAXYS Number:
1524564

Key Documents

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InChI

1S/C7H15NO4/c1-8-2-5(10)7(12)6(11)4(8)3-9/h4-7,9-12H,2-3H2,1H3/t4-,5+,6-,7-/m1/s1

SMILES string

CN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO

InChI key

AAKDPDFZMNYDLR-XZBKPIIZSA-N

biological source

synthetic (organic)

assay

≥98%

form

powder

solubility

methanol: 10 mg/mL, clear, colorless

antibiotic activity spectrum

viruses

mode of action

enzyme | inhibits

storage temp.

−20°C

Quality Level

200

Gene Information

mouse ... Gaa(14387), Glb1(12091), Treh(58866)
rat ... Man2a1(25478), Si(497756)

Related Categories

General description

Chemical structure: glucosamine

Biochem/physiol Actions

Interferes with metabolism of N-linked glycoproteins by inhibition of glucosidase.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLCJ3887
SLCH8326
SLBX5322
SLBK5342V
SLBG5787V

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Diego A Caraballo et al.
G3 (Bethesda, Md.), 10(2), 755-768 (2019-12-05)
UDP- glucose: glycoprotein glucosyltransferase (UGGT) is a protein that operates as the gatekeeper for the endoplasmic reticulum (ER) quality control mechanism of glycoprotein folding. It is known that vertebrates and Caenorhabditis genomes harbor two uggt gene copies that exhibit differences
G C Trudel et al.
Biochemistry and cell biology = Biochimie et biologie cellulaire, 66(10), 1119-1125 (1988-10-01)
It has recently been reported that the glucosidase I inhibitor, N-methyl-1-deoxynojirimycin (MDJN), inhibits myoblast fusion whereas the mannosidase inhibitor, 1-deoxymannojirimycin (ManDJN), has no effect on fusion. We now report that bromoconduritol, which is an active-site-directed covalent inhibitor of glucosidase II
D J Wu et al.
Japanese circulation journal, 65(7), 673-677 (2001-07-12)
N-methyl-1-deoxynojirimycin (NMDN), an a-glucosidase inhibitor, reduces myocardial infarct size by reducing the glycogenolytic rate through inhibition of the alpha-1,6-glucosidase of glycogen-debranching enzyme in the heart, in addition to possessing an antihyperglycemic action by blocking alpha-1,4-glucosidase in the intestine. Ischemic preconditioning
K Matter et al.
The Journal of biological chemistry, 264(22), 13131-13139 (1989-08-05)
Intestinal brush border enzyme glycoproteins are transported to the microvillar membrane at different rates in the differentiated intestinal cell line Caco-2. This asynchronism is due to at least two rate-limiting events, a pre- and an intra-Golgi step (Stieger B., Matter
J C Ridruejo et al.
Biochimica et biophysica acta, 993(2-3), 179-185 (1989-12-08)
Castanospermine, 1-deoxynojirimycin, and N-methyl-1-deoxynojirimycin, three well-characterized inhibitors of the glucosidases involved in the processing of N-linked oligosaccharides, did not affect the biosynthesis or the secretion of exoglucanases (EC 3.2.1.58) from Saccharomyces cerevisiae and Candida albicans but inhibited the activity itself.
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