Heroin metabolites

F. Munari and K. Grob, Automated on-line HPLC-HRGC instnimental aspects and application for the determination of heroin metabolites in urine , J. High. Resolut. Chromatogr. Chromatogr. Commun. 11 172-176(1988). 

J. J. Rady, F. Aksu, J. M. Fujimoto, The Heroin Metabolite, 6-Monoacetylmorphine, Activates delta Opiod Receptors to Produce Antinociception in Swiss-Webster Mice ,... 

A morphine level of 2000 ng/ml or more requires a test for 6-monoacetylmorphine (6-MAM, heroin metabolite) with a cutoff at 10 ng/ml. ... 

Moghaddam, A., Borgen, T., Stacy, J., Kausmally.L., Simonsen, B., Marvik, O. J., et al. (2003) Identification of scFv antibody fragments that specifically recognise the heroin metabolite 6-monoacetyl-morphine but not morphine. /. Immunol. Meth. 280, 139-155. 

Initial studies performed during the late 1970s and early 1980s revealed the presence of benzoylecgonine (cocaine metabolite) and morphine (heroin metabolite) in hair. Since then, fiu-ther studies of hair analysis have identified additional cocaine analytes and opioids. The aim of this chapter is to provide a review of the analytical techniques utilized in hair analysis, including preliminary wash/decontamination procedures, methods of analyte isolation and pmification, and analysis of the hair extracts. In addition, this chapter will present research findings. 

Another unique property of hair is the efficient trapping of the short-lived heroin metabolite 6-monoacetylmorphine (6-MAM). " In contrast to hair, this metabolite is rarely found in opiate-positive urines, thereby causing 90% of such urine results to be overturned by medical review officers. The special procedures required for hair analysis to help resolve the opiate-positive problems of urinalysis will be described. 

Other definitive metabolites which are used in our laboratory as indicators of drug use are cocaethylene, norcocaine, A9-carboxy-tetrahydrocaimabinol (carboxy-THC) (a substance which is not found in smoke from a marijuana cigarette), and the heroin metabolites 6-MAM and morphine glucuronide. Drugs and metabolites are measured by ultrasensitive GC/MS/MS or chemical ionization ion-trap GC/MS techniques requiring 5 mg or less of sample. ... 

The determination of the heroin metabolites morphine, morphine-6-glucuronide (M6G), morphine-3-glucuronide (M3G), and 6-monoacetyhnorphine (6-MAM) in body fluids is an important application of LC-MS in the toxicology laboratory. In some cases, codeine and codeine-6-glucuronide are determined as well. Several quantitative methods have been reported. However, only a few deal with forensic toxicology, performing the analysis in urine, serum, vitreous humour [79], and autopsy whole blood [79-80]. 

It has also been demonstrated that, in humans, the time course of heroin in plasma and the appearance and disappearance of heroin metabolites after inhalation and IV administration are similar (Jenkings et al. 1994). The half-lives of heroin after smoking and IV administration were 3.3 and 3.6 minutes, respectively. 

Low, A.S. Taylor, R.B. Analysis of common opiates and heroin metabolites in urine by high-performance liquid chromatography. J.Chromatogr.B, 1995, 663, 225-233... 

Qi, X. H., Mi, J. Q., Zhang, X. X., and Chang, W. B. Design and preparation of novel antibody system and application for the determination of heroin metabolites in urine by capillary electrophoresis, Analytica Chimica Acta, 551, 115, 2005. 

For analysis of heroin metabolites, reversed-phase chromatography coupled with electrochemical detection is frequently used. Other methods used to improve sensitivity include oxidation to fluorescent pseudomorphine-like dimers using potassium hexa-cyanoferrate(III) and derivatization using a fluorescent chromophore such as dansyl chloride. Detection by MS or tandem MS after separation by LC is... 

Heroin is generally present in biological fluids and tissues at very low concentrations, whereas the metabolites 6-acetylmorphine and morphine may be present in much higher concentrations. Consequently, heroin metabolites are frequently measured by GC with flame ionization, nitrogen-phosphorus, electron-capture detection, or MS. Depending upon the chromatographic system, derivatization of 6-acetylmorphine and morphine to perfluorinated or silylated derivatives is performed to improve analyte volatility, aid chromatographic performance, and enhance detector response. 

W. Hanisch and L.V. Meyer, Determination of the heroin metabolite 6-monoacetyl-morphine in urine by high-performance liquid chromatography with electrochemical detection, J. Anal. Toxicol, 1993, 17, 48-50. 

UDP-glucuronosyltransferase-2B7 (UGT2B7). M6G can accumulate to toxic levels in kidney failure. The opioid receptor subtype 3 appears to be activated (agonized) by morphine-6 p-glucuronide but not morphine itself. This finding is also tme of certain heroin metabolites (6-MAM) but not morphine proper. This analgesic activity of M6G (in animals) was first noted by Yoshimura (Fig. 15.5). 

Jong Y-J, Ho Y-H, Ko W-K, Wu S-M (2009) On-line stacking and sweeping capillary electrophoresis for detecting heroin metabolites in human urine. J Chromatogr A 1216(44) 7570-7575... 

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