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Chlorinated Opium Alkaloid Derivatives Produced by the Use of Aqueous Sodium Hypochlorite During the Clandestine Manufacture of Heroin
Author(s) -
Casale John F.,
Toske Steven G.,
Hays Patrick A.
Publication year - 2009
Publication title -
journal of forensic sciences
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.715
H-Index - 96
eISSN - 1556-4029
pISSN - 0022-1198
DOI - 10.1111/j.1556-4029.2009.00985.x
Subject(s) - chemistry , sodium hypochlorite , opium , sodium hydroxide , alkaloid , chlorine , heroin , organic chemistry , ammonium hydroxide , chromatography , drug , pharmacology , political science , law , medicine
A clandestine chemist was observed producing heroin from crude morphine utilizing a solution of sodium hypochlorite during the process. Numerous chlorinated opium alkaloid derivatives were created when the morphine acetylation reaction was quenched and neutralized with a solution of sodium hypochlorite and ammonium hydroxide. Four of these compounds, 1‐chloroheroin, 1‐chloroacetylcodeine, 1‐chloro‐O 6 ‐monoacetylmorphine, and 2′‐chloropapaverine, were characterized via preparative isolation, gas chromatography/mass spectrometry, nuclear magnetic resonance spectroscopy, and independent synthesis. These chlorinated derivatives were formed via electrophilic aromatic substitution with free chlorine during the illicit process. Although no illicit heroin exhibits containing these compounds have been observed in seizures to date, mass spectral data are provided for several of these compounds for their identification should they be seen within future seizures of illicit heroin.