Heteroalicyclic analogs of 2- and 3-aminoalkanethiols were synthesized from the alkanols Ia--Va via the corresponding halogenoalkylamine hydrohalides for evaluation as antiradiation drugs. The analogs described have mercapto (or potential mercapto) groups on a side chain two or three carbon atoms removed from the secondary amino groups of pyrrolidine, piperidine, thiomorpholine, and piperazine. The bicyclic dithiocarbamates VIII and IX resulted from the reaction of carbon disulfide with 2-(chloromethyl) pyrrolidine hydrochloride (Ib) and 2-(2- chloroethyl)piperidine hydrochloride (IIIc), respectively. The synthesis of VIII elucidated the structure of the water-insoluble product formed concurrently with 2-pyrrolidinylmethyl dimethyldithiocarbamate hydrochloride (Id) from Ib and sodium dimethyldithiocarbamate.