Oripavine as a new marker of opiate product use

• Published in: Forensic toxicology Vol. 29; no. 2; pp. 152 - 158
• Main Authors: El-Haj, Babiker M., Ali, Heyam S., Hamoudi, Nehad M.
• Format: Journal Article
• Language: English
• Published: Japan Springer Japan 01.07.2011
• Subjects: Forensic Medicine; Forensic Science; Medical Law; Medicinal Chemistry; Medicine; Medicine & Public Health; Original Article; Pharmacology/Toxicology; Marker of opiate product use; GC–MS; Opium; Thebaine metabolism; Oripavine; Poppy seed
• ISSN: 1860-8965; 1860-8973
• DOI: 10.1007/s11419-011-0117-2

During our extensive surveillance of opiates in urine specimens of opium users, we noticed the appearance of an unknown peak (compound X) in total ion chromatograms obtained by gas chromatography-mass spectrometry (GC–MS) after enzymatic hydrolysis and trimethylsilyl (TMS) derivatization. We identified the compound X as oripavine. Oripavine was found to be a new and useful putative marker of opium/poppy seed use in differentiation from heroin, pharmaceutical codeine, and pharmaceutical morphine use. The presence of oripavine in the urine of opium users is probably the result of O -demethylation of the opium alkaloid thebaine. Analytical method optimization for GC–MS detection of oripavine in urine was also undertaken. Underivatized oripavine could not be detected by GC–MS, and trials for derivatization of oripavine with acetic anhydride and propionic anhydride were unsuccessful. Trials were successful with bis(trimethylsilyl)trifluoroacetamide/trimethylchlorosilane. It was also disclosed that almost all amounts of oripavine in human urine existed in the unconjugated form; it was absolutely necessary to hydrolyze the conjugate before TMS derivatization of oripavine for its GC–MS analysis.