N,N-Dihexyl-D-erythro-sphingosine

N,N-Dihexyl-D-erythro-sphingsosine is an unnatural analog of the vital sphingolipid ceramide. Ceramide functions as a precursor in the synthesis of sphingomyelin, complex glycosphingolipids, and free sphingosine and it exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.1 Instead of the normal fatty acid acylated to sphingosine N,N-Dihexyl-D-erythro-sphingsosine contains two hexyl groups making it a tertiary amine rather than secondary. Ceramide analogs, such as N,N-Dihexyl-D-erythro-sphingsosine, are able to induce an a increase in ceramide levels in cells, leading to apoptosis, and may be useful in treating certain diseases.2 N-Hexyl-glucosylceramide is a potent inhibitor of glucosylceramidase, the enzyme responsible for cleaving glucose from glucosylceramide.3