GC-MS detection and tentative characterization of two noscapine metabolites in human urine and their potential as markers for opium and illicit heroin use

El‐Haj, Babiker M.; Al-Amri, Abdelkader M.; Ali, Heyam Saad

doi:10.1007/s11419-007-0023-9

Cited by 4 publications

(4 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…From all urine samples with morphine present as the major opiate, meconine was detected in 94.7% of the substance misuse samples and in 78% of the post‐mortem samples, suggesting meconine as a useful adjunct in detecting illicit opiate use. Two further metabolites that were suggested as potential markers of opium and illicit heroin use were detected in 2007 by El‐Hej et al, and were assigned as 6,7‐dihydroxynoscapine and its desmethyl product at either position 6′ or 7′, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…Besides noscapine, meconine is also sometimes present as a minor impurity in illicit heroin samples. [177][178][179] In a previous study by McLachlan-Troup et al, 180 1122 urine samples from clients of an urban substance misuse service were investigated for the potential to distinguish between the use of street Two further metabolites that were suggested as potential markers of opium and illicit heroin use were detected in 2007 by El-Hej et al, 183 and were assigned as 6,7-dihydroxynoscapine and its desmethyl product at either position 6′ or 7′, respectively.…”

Section: Othersmentioning

confidence: 99%

See 1 more Smart Citation

Confirmation of recent heroin abuse: Accepting the challenge

Maas

Madea

Heß

2017

Drug Testing and Analysis

View full text Add to dashboard Cite

Confirmation or exclusion of recent heroin consumption is still one of the major challenges for forensic and clinical toxicologists. A great variety of biomarkers is available for heroin abuse confirmation, including various opium alkaloids (eg, morphine, codeine), street heroin impurities (eg, 6-acetylcodeine [6-AC], noscapine, papaverine) as well as associated metabolites (eg, 6-monoacetylmorphine [6-MAM], morphine glucuronides). However, the presence of most of these biomarkers cannot solely be attributed to a previous heroin administration but can, among other things, also be due to consumption of poppy seed products ('poppy seed defense'), opium preparations or specific medications, respectively. A reliable allocation is of great importance in different contexts, for instance in the case of DUID (driving under the influence of drugs) investigations, in driving licence re-granting processes, in workplace drug testing (WDT), as well as in post-mortem identification of illicit opiate use. Additionally, differentiation between illicit street heroin abuse and pharmaceutical heroin administration is also important, especially within the frame of heroin-assisted treatments. Therefore, analysis of multiple biomarkers is recommended when illicit opiate consumption is assumed to obtain the most reliable results possible. Beyond that, interpretation of positive opiate test results requires a profound insight into the great variety of biomarkers available and their validity regarding the alleged consumption. This paper aims to provide an overview of the wide variety of heroin abuse biomarkers described in the literature and to review them regarding their utility and reliability in daily routine analysis.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Othersmentioning

confidence: 99%

Confirmation of recent heroin abuse: Accepting the challenge

Maas

Madea

Heß

2017

Drug Testing and Analysis

View full text Add to dashboard Cite

show abstract

“…After evaporation of the excess derivatizing reagent under nitrogen at 50°C, the residue was [3]), neopine (P; [4]), thebaine (P; [5]) noscapine-Ms (P; [4]), papaverineMs (P; [6])…”

Section: Urine Sample Preparation For Gc-ms Analysismentioning

confidence: 99%

“…Among the different classes of drugs of abuse, search for markers of opiate product use has attracted the most attention [3][4][5][6][7][8][9][10][11][12][13][14][15], because legal questions are often raised about which form of licit or illicit products has been used. The different opiate products, their psychoactive constituents, legal status, and published urinary markers are given in Table 1.…”

Section: Introductionmentioning

confidence: 99%

Oripavine as a new marker of opiate product use

2011

Self Cite

View full text Add to dashboard Cite

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.Keywords Oripavine Á Marker of opiate product use Á Opium Á Poppy seed Á Thebaine metabolism Á GC-MS

show abstract

General unknown screening procedure for the characterization of human drug metabolites in forensic toxicology: Applications and constraints

Sauvage

Picard

Saint-Marcoux

et al. 2009

J of Separation Science

View full text Add to dashboard Cite

LC coupled to single (LC-MS) and tandem (LC-MS/MS) mass spectrometry is recognized as the most powerful analytical tools for metabolic studies in drug discovery. In this article, we describe five cases illustrating the utility of screening xenobiotic metabolites in routine analysis of forensic samples using LC-MS/MS. Analyses were performed using a previously published LC-MS/MS general unknown screening (GUS) procedure developed using a hybrid linear IT-tandem mass spectrometer. In each of the cases presented, the presence of metabolites of xenobiotics was suspected after analyzing urine samples. In two cases, the parent drug was also detected and the metabolites were merely useful to confirm drug intake, but in three other cases, metabolite detection was of actual forensic interest. The presented results indicate that: (i) the GUS procedure developed is useful to detect a large variety of drug metabolites, which would have been hardly detected using targeted methods in the context of clinical or forensic toxicology; (ii) metabolite structure can generally be inferred from their "enhanced" product ion scan spectra; and (iii) structure confirmation can be achieved through in vitro metabolic experiments or through the analysis of urine samples from individuals taking the parent drug.

show abstract

GC-MS detection and tentative characterization of two noscapine metabolites in human urine and their potential as markers for opium and illicit heroin use

Cited by 4 publications

References 16 publications

Confirmation of recent heroin abuse: Accepting the challenge

Confirmation of recent heroin abuse: Accepting the challenge

Oripavine as a new marker of opiate product use

General unknown screening procedure for the characterization of human drug metabolites in forensic toxicology: Applications and constraints

Contact Info

Product

Resources

About