Electron ionization mass fragmentometric detection of urinary ecgonidine, a hydrolytic product of methylecgonidine, as an indicator of smoking cocaine

A study on the stability of anhydroecgonine methyl ester (crack biomarker), benzoylecgonine, and cocaine in human urine

“…AME is the principal thermal breakdown product of COC, it is not formed metabolically and therefore recognized as a specific marker for smoked cocaine (Paul et al, 1999;Shimomura et al, 2001). The distinction between the inhalation of cocaine and nasal insufflation or injection has forensic and medical implications.…”

“…The extent of artifact production depends on the injection port type, so other analysts might experience a lower or higher degree (Toennes et al, 1999) and the use of a clean insert liner to minimize artifact production (Toennes et al, 2003). Because BE is excreted over a longer period of time, its detection in biological specimens is utilized in most clinical and forensic investigations to infer cocaine use (Paul et al, 1999). In other hand, the stability study of analytes in urine provides additional information for adequate interpretation of results.…”

“…Smoking also causes an intense craving for additional drug. During the smoking of crack, AME is formed as a result of the elimination of benzoic acid from COC under the high temperature conditions of pyrolysis and this analyte has been identified in the urine of crack smokers (Zhang and Foltz, 1990;Paul et al, 1999;Kintz et al, 1995;Shimomura et al, 2001), with most subjects excreting substantial amounts of AME averaging approximately half the molar amounts of COC excreted during a 48 hr collections period (Jacob et al, 1990). In general, AME concentrations are much higher in urine than in other biological specimens (Shimomura et al, 2001).…”

Pharmacokinetics and Pharmacodynamics of Methylecgonidine, a Crack Cocaine Pyrolyzate

“…Because methylecgonidine is produced via thermal conversion from cocaine, it can be used as a marker to differentiate between smoking and cocaine use via other routes of administration. In forensic cases, methylecgonidine has been detected in urine (Jacob et al, 1990;Cone et al, 1994;Paul et al, 1999;Riley et al, 2001;Shimomura et al, 2001), blood/ plasma (Jenkins and Goldberger, 1997;Toennes et al, 1999;Shimomura et al, 2001;Fandino et al, 2002;Toennes et al, 2003), saliva (Kintz et al, 1997), perspiration (Kintz et al, 1997), hair (Kintz et al, 1995(Kintz et al, , 1997, and brain and liver (Shimomura et al, 2001) of crack smokers. Although methylecgonidine has been identified in numerous matrices, the number of blood or plasma samples in which it has been detected numbers less than 50 in the literature.…”

“…Methylecgonidine is metabolized to ecgonidine (anhydroecgonine) by butyrylcholine esterase activity, accounting for the presence of ecgonidine in urine and postmortem brain and liver (Paul et al, 1999;Shimomura et al, 2001;Fandino et al, 2002) (Fig. 1A).…”