Technical Abstract: The linkage of swainsonine to a large carrier molecule (protein) for the purpose of the induction of immunological activity has proven difficult because of the lack of chemical handles on such a small molecule. Swainsonine has been linked via the hydroxyls but no swainsonine specific antibodies were produced. It was assumed that linkage through one of the hydroxyl groups most likely destroys the three dimensional structure that characterizes the swainsonine-specific epitope. We sought an alternate approach by searching for a possible link through the nitrogen. Several N-alkyl derivatives of swainsonine were produced through the reaction of swainsonine acetonide with di-bromo and di-iodo alkyl compounds. In acetonitrile and at high molar excess, 1,4-diiodobutane as found to react to produce N-(1-iodobutane)swainsonine acetonide. This derivative proved to be stable and the acetonide group removed upon the addition of hydroiodoic acid. The N-iodobutaneswainsonine derivative could be further reacted with sulfhydryl (SH) groups as demonstrated with the amino acid cysteine. This derivative was found to react poorly with amine (NH) and hydroxyl (OH) functional group amino acids. Alternatively, swainsonine acetonide was reacted with 1,4-dibromobutene and the acetonide removed upon reaction with hydrobromic acid. The N-bromobuteneswainonine derivative was found to be highly reactive towards OH, SH and NH groups, but these reactions were also highly reversible.