Inhibitor of glucosylceramide synthase and non-lysosomal glucosylceramidase
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AMP-Deoxynojirimycin

Item No. 10010332

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2R-(hydroxymethyl)-1-[5-(tricyclo[3.3.2.13,7]dec-1-ylmethoxy)pentyl]-3R,4R,5S-piperidinetriol
CAS Number
216758-20-2
Synonyms
  • Adamantane-pentyl-dNM
  • AMP-DNJ
  • AMP-dNM
  • N-(5-adamantane-1-yl-methoxy-pentyl)-Deoxynojirimycin
Molecular Formula
C22H39NO5
Formula Weight
397.6
Purity
≥95%
Formulation
A 5 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
SMILES
OC[C@H]1N(CCCCCOCC23CC4CC(CC(C4)C3)C2)C[C@H](O)[C@@H](O)[C@@H]1O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    5 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    AMP-deoxynojirimycin (AMP-dNM) is a hydrophobic derivative of dNM. It potently inhibits BGD (IC50 = 0.3 nM), less potently antagonizes GCS (IC50 = 25 nM), but only poorly inhibits other GCase isoforms.1,2 AMP-dNM has been shown to strongly suppress inflammation in a murine model of hapten-induced colitis, enhance insulin sensitivity in murine and rat models of insulin resistance, and induce sterol regulatory element-binding protein-regulated gene expression and cholesterol synthesis in HepG2 cells.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Overkleeft, H.S., Renkema, G.H., Neele, J., et al. Generation of specific deoxynojirimycin-type inhibitors of the non-lysosomal glucosylceramidase. The Journal of Biological Chemisty 273(41), 26522-26527 (1998).

    2. Aerts, J.M., Hollak, C., Boot, R., et al. Biochemistry of glycosphingolipid storage disorders: Implications for therapeutic intervention. Philos. Trans. R. Soc. Lond. B Biol. Sci. 358(1433), 905-914 (2003).

    3. Bijl, N., Scheij, S., Houten, S., et al. The glucosylceramide synthase inhibitor N-(5-adamantane-1-yl-methoxy-pentyl)-deoxynojirimycin induces sterol regulatory element-binding protein-regulated gene expression and cholesterol synthesis in HepG2 cells. J. Pharmacol. Exp. Ther. 326(3), 849-855 (2008).

    4. Shen, C., Bullens, D., Kasran, A., et al. Inhibition of glycolipid biosynthesis by N-(5-adamantane-1-yl-methoxy-pentyl)-deoxynojirimycin protects against the inflammatory response in hapten-induced colitis. Int. Immunopharmacol. 4(7), 939-951 (2004).

    5. Aerts, J.M., Ottenhoff, R., Powlson, A.S., et al. Pharmacological inhibition of glucosylceramide synthase enhances insulin sensitivity. Diabetes 56(5), 1341-1349 (2007).

    Product Citations

    Ridley, C.M., Thur, K.E., Shanahan, J., et al. β-Glucosidase 2 (GBA2) activity and imino sugar pharmacology. The Journal of Biological Chemisty 288(36), 26052-26066 (2013).