title: Chemistry of nitrosoureas. Decomposition of Deuterated 1,3-bis(2-chloroethyl)-1-nitrosourea.
abstract: BCNU-alpha-d4 [1,3-bis(2-chloro-1,1-dideuterioethyl)-1-nitrosourea] and BCNU-beta-d4 [1,3-bis(2-chloro-2,2-dideuterioethyl)-1-nitrosourea] were synthesized and decomposed in buffered (pH 7.4)water. The products were analyzed by GC-MS. The deuterium distribution in the products is inconsistent with vinylcarbonium ion or diazochloroethane intermediacy but is consistent with a 2-chloroethylcarbonium ion intermediate with some rearrangement to the 1-chloroethylcarbonium ion and the cyclic chloronium ion.
mesh_terms: D002330:Carmustine; D055598:Chemical Phenomena; D002621:Chemistry; D003903:Deuterium; D007553:Isotope Labeling; D013058:Mass Spectrometry
chemical_list: D003903:Deuterium; D002330:Carmustine