Illicit Heroin Manufacturing Byproducts: Copillary Gas Chromatographic Determination and Structural Elucidation of Narcotine- and Norlaudanosine-Related Compounds

Article abstract of DOI:10.1021/ac00278a072

Capillary gas chromatographic methodology is described for detection of trace quantities of narcotine- and norlaudanosine-related manufacturing impurities in illicit heroin.N-Acetylnornarcotine (2), N-acetylanhydronornarceine (3a,b), 1-acetoxy-N-acetylanhydro-1,9-dihydronornarceine (4a,b),and (E)-3-<2-(2-(N-methylacetamido)ethyl)-4,5-(methylenedioxy)-6-methoxyphenyl>acrylic acid(5) result from the reaction of narcotine (1) with acetic anhydride.The treatment of norlaudanosine (11a) with acetic anhydride yields N-acetylnorlaudanosine (9).After isolation from thebulk heroin matrix, these impurities, along with morphine, codeine, and thebaine byproducts, are detected by using both fused silica and glass capillary columns in the split mode with flame ionization detection.The syntheses and spectral characterization of these impurities are described.