N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN Chemical Properties

Boiling point:

569.9±50.0 °C(Predicted)

Density 

1.214±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml

pka

13.72±0.70(Predicted)

form 

powder

color 

white to beige

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

InChIKey

XVYLNHVEAOOEGI-OIPNBASOSA-N

SMILES

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

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN Usage And Synthesis

Chemical Properties

Off White Foam

Uses

A powerful inhibitor of the non-lysomal glucoceramidase at nanomolar concentrations. At these low concentrations, the lysosomal glucocerebrosidase and a-glucosidase, the glucoceramide synthetase, and the N-linked glycantrimming a-glucosidases of the endoplasmic reticulum are not affected.

Biological Activity

AMP-deoxynojirimycin (AMP-DNM) is an orally available iminosugar th at 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).

N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN(216758-20-2)Related Product Information

• 1-Adamantanemethanol
• N-BUTYLDEOXYNOJIRIMYCIN
• 1-Deoxynojirimycin
• N-METHYL-1-DEOXYNOJIRIMYCIN
• N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN