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
• Empirical Formula (Hill Notation): C₂₂H₃₉NO₅
• CAS Number: 216758-20-2
• Molecular Weight: 397.55
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• assay: ≥97% (HPLC)
• form: powder
• storage condition: desiccated
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: -10 to -25°C
• 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

Description

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).

Caution

Hygroscopic

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable