Skip to Content
Merck
CN

SML3666

AMP-Deoxynojirimycin

≥97% (HPLC)

Synonym(s):

AMP-dNJ, AMP-dNM, (2R,3R,4R,5S)-2-(Hydroxymethyl)-1-[5-(tricyclo[3.3.1.13,7]dec-1-ylmethoxy)pentyl]-3,4,5-piperidinetriol, AMP-DNJ, AMP-DNM, Adamantane-pentyl-DNM, Adamantane-pentyl-dNM, MZ-21, N-(5′-Adamantane-1′-yl-methoxy)pentyl-1-deoxynojirimycin; (2R,3R,4R,5S)-1-[5-(1-Adamantylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol, N-(5-Adamantane-1-yl-methoxy)pentyl-1-deoxynojirimycin; N-(5-Adamantane-1-yl-methoxy)pentyl)-DNM

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C22H39NO5
CAS Number:
216758-20-2
Molecular Weight:
397.55
UNSPSC Code:
51111800
NACRES:
NA.21

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

InChI

1S/C22H39NO5/c24-13-18-20(26)21(27)19(25)12-23(18)4-2-1-3-5-28-14-22-9-15-6-16(10-22)8-17(7-15)11-22/h15-21,24-27H,1-14H2/t15-,16+,17-,18-,19+,20-,21-,22?/m1/s1

InChI key

XVYLNHVEAOOEGI-OIPNBASOSA-N

SMILES string

O[C@@H]1[C@H](N(C[C@@H]([C@H]1O)O)CCCCCOCC2(C3)C[C@@H](C4)C[C@H]3C[C@@H]4C2)CO

assay

≥97% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Quality Level

100

Related Categories

Biochem/physiol Actions

AMP-deoxynojirimycin (AMP-DNM) is an orally available iminosugar that acts as a reversible, potent and selective inhibitor against the non-lysosomal glucosylceramidase GBA2 (IC50 = 1.7 nM) over the glucosylceramide synthase (GCS, UGCG), ER alpha-glucosidases, the lysosomal glucocerebrosidase GBA (IC50 = 0.16 μM) and alpha-glucosidase GAA (IC50 = 0.87 μM). AMP-DNM selectively inhibits cellular GBA2 in cultures (GBA2/GBA IC50 = 0.3 nM/100 nM; human melanoma cells) and exhibits in vivo therapeutic efficacy in murine models of obesity (100 mg/kg/day p.o.) and colitis (10-50 mg/kg/day via i.p. or 1.25-6.25g/kg chow).
Orally available, potent, selective non-lysosomal glucosylceramidase GBA2 inhibitor with therapeutic efficacy in murine models of obesity and colitis in vivo.

Disclaimer

Hygroscopic

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

新产品
This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000272691
0000272693
0000256060
0000256060
0000272693

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Generation of specific deoxynojirimycin-type inhibitors of the non-lysosomal glucosylceramidase
The Journal of biological chemistry, 273(41), 26522-26527 (1998)
Treatment of genetically obese mice with the iminosugar N-(5-adamantane-1-yl-methoxy-pentyl)-deoxynojirimycin reduces body weight by decreasing food intake and increasing fat oxidation
Metabolism, Clinical and Experimental, 61(1), 99-107 (2012)
Cytosolic glucosylceramide regulates endolysosomal function in Niemann-Pick type C disease
Neurobiology of Disease, 127, 242-252 (2019)
Species-specific differences in nonlysosomal glucosylceramidase GBA2 function underlie locomotor dysfunction arising from loss-of-function mutations
The Journal of Biological Chemistry, 294(11), 3853-3871 (2019)
Reduction of glycosphingolipid biosynthesis stimulates biliary lipid secretion in mice
Hepatology, 49(2), 637-645 (2009)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service