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Detection of D,L-Amphetamine, D,L-Methamphetamine, and Illicit

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Detection of D,L-Amphetamine, D,L-Methamphetamine, and Illicit Journal of Analytical Toxicology, Vol. 14, September/October 1990 Technical Note I Detection of D,L-Amphetamine, D,L-Methamphetamine, and Illicit Amphetamine Analogs Using Diagnostic Products Corporation's Amphetamine and Methamphetamine Radioimmunoassay* John T. Cody Air Force Drug Testing Laboratory, Brooks AFB, Texas 78235-5000 samples for drugs of abuse mayor may not detect an analog. I Abstract I Because of the ease of synthesis, numerous illicit analogs of am- phetamine have appeared. The structure of amphetamine can be Cross-reactivity with Diagnostic Products Corporation (DPC) altered by substitution of the ethyl amine or on the benzene ring. amphetamine and methamphetamine radioimmunoassay (RIA) These modifications may retain the stimulant properties of am- reagents was determined for amphetamine, methamphetamine, phetamine or extend them. Recentlyseveral amphetamine analogs and a number of amphetamine analogs. Concentrations from have been seen on the illicit market with increasing frequency. 100 to 100,000 ng/mL were assayed. 3,4-Methylenedioxyam- One of the most common is "esctasy" (MDMA), which remains phetamine (MDA) and 3,4-methylenedioxymethamphetmaine popular even after its placement on the schedule of controlled (MDMA) showed significant cross-reactivity for the amphetamine substances in 1988. Other amphetamine analogs that have not and methamphetamine reagents respectively. 4-Hydroxymeth- amphetamine, 3,4-methylenedioxyethylamphetamlne (MDEA), been popular for some time have reappeared in clandestine and N,N-dimethyl-MDA also showed significant cross-reactivity laboratories. An example of this is the seizure of 4-bromo- with the methamphetamine reagents, but less than MDMA. None 2,5-dimethoxyamphetamine (DaB) by the DEA in 1989. Lawen- of the other analogs showed a positive result with the forcement efforts that address the starting materials for one il- amphetamine or methamphetamine reagents at even the highest licit drug often prompt the synthesis from another starting concentration, although several did show measurable cross- material or the synthesis of another drug. To evaluate the ability reactivity. The L isomers of amphetamine and methamphet- of commercial screening methods to identify these compounds, amine showed substantially less cross-reactivity than the 0 a number of amphetamine analogs were tested with the double forms to which the respective antibody systems are targeted. antibody for amphetamine assay and the Coat-a-Count metham- phetamine assay from Diagnostic Products Corporation (DPC). Introduction Abuse of amphetamine, methamphetamine, and amphetamine Materials and Methods analogs is neither a new nor unique phenomenon but is currently a significant problem. Although amphetamine abuse is not Materials. 2-Methoxyamphetamine, 4-hydroxymethamphet- widespread in the U,S., methamphetamine abuse is and there amine, 2,5-dimethoxyamphetamine (DMA), DaB, 4-bromo- is growing interest and concern over "ice", the solid form of 2,5-dimethoxy-B-phenethylamine (BDMPEA), 3,4,5-trimethoxy- methamphetamine. The use of amphetamine analogs poses not amphetamine (TMA), 3,4-methylenedioxyamphetamine (MDA), only societal concerns but also analytical challenges. Many am- N,N-dimethyl-3,4-methylened.ioxyamphetarnine, and N-hydroxy- phetamine analogs from the illicit market of the 1960s have been 3,4-methylenedioxyamphetamine (N-OB MDA) were obtained reintroduced and new analogs have recently surfaced. New from the National Institute on Drug Abuse (NIDA). 3,4-Methyl- analogs have been synthesized and marketed for increased enedioxymethamphetamine (MDMA), 3,4-methylenedioxyethyl- potency, altered pharmacological effects, and difficulty of detec- amphetamine (MDEA), 2,5-dimethoxy-4-ethylamphetamine tion and prosecution. In some cases, synthesis of an analog (DOE), 2,5-dimethoxy-4-methylamphetamine (DOM), 3,4,5-tri- yielded a compound not under the schedule of illegal drugs and methoxyphenethylamine (mescaline) and L-methamphetamine which therefore could be prepared, marketed, and used without were obtained from Alltech. D- and L-amphetamine and n-meth- interference from law enforcement agencies. To address this amphetamine were obtained from Sigma. Amphetamine and problem, the Controlled Substance Analogue Act was enacted methamphetamine RIA reagents were obtained from DPC. to prevent synthesis of new unscheduled drugs of abuse. Sample preparation. Solutions of test compounds were pre- Standard methods commonly used for screening biological pared in ethanol and stored at 4°C. These drug solutions were mixed with negative control resulting in final concentrations ranging from 100 to 100,000 ng/mL. • Presented at the annual meeting of the International Association of Forensic Toxicologists, Glasgow, Scotland, August 14-19, 1989. Amphetamine test. Radiommunoassay analysis was per- 321 Journal of Analytical Toxicology, Vol. 14, September/October 1990 formed with the double antibody for amphetamine from DPC tested in this study were consistent with this statement, 4-meth- essentially as described by the manufacturer (1,2). For the am- oxyamphetamine was not tested and may be predicted to have phetamine test, 25 JLLof sample were placed into a 12- x 75-mm higher cross-reactivity than methoxyamphetamines tested in this tube, to which was added 200 JLLof IlSI amphetamine and study. Structures of compounds that showed substantial cross- 100 JLLof amphetamine antiserum. The racks were shaken to reactivity are shown in Figure 1. Results from compounds that thoroughly mix the components. After incubation at room did not demonstrate significant measurable cross-reactivity to temperature for an hour, 1.0 mL of the cold precipitating solu- the amphetamine reagents are found in Table III. tion was added to each tube and the racks were again shaken. MDMA demonstrated significant cross-reactivity to the The racks were then centrifuged for 15min at 3,000 g, the super- methamphetamine reagents. The methylenedioxy group substan- natant was decanted, and the precipitate counted on a Micro- tially enhanced the binding of the MDMA, giving a result . medic 10/600 gamma counter. equivalent to 1,000 ng/mL of D-methamphetamine at a con- Methamphetamine test. The methamphetamine procedure centration between 200 and 300 ng/mL. This high degree of with the Coat-a-Count methamphetamine reagents was similar cross-reactivity becomes even more significant when one con- to that of the amphetamine assay except it involved antibody- siders that the MDMA in this study was the racemic mixture coated tubes rather than a double antibody system, thus and racemic methamphetamine is only 67% cross-reactive when eliminating addition of antibody solutions and centrifugation. compared to D-methamphetamine at 1,000 ng/mL. MDEA and 25 JLLof sample was placed into a 12- x 75-mm metham- 4-hydroxymethamphetamine both gave positive results at con- phetamine antibody-coated polypropylene tube, to which was centrations of 2,000-3,000 ng/mL. The degree of cross-reactivity added 1.0 mL of 12SImethamphetamine solution. The racks were demonstrated with N,N-dimethyl-MDA would require approx- shaken and then incubated at room temperature for one hour. imately 25 JLg/mL to produce a positive result (assuming a The tubes were then thoroughly decanted to remove all liquid. 1,000-ng/mL cutoff). Results of the MDMA, MDEA, 4-hy- The tubes were counted on a Micromedic 10/600 gamma counter. droxymethamphetamine, and N,N-dimethyl-MDA testing are Positive and negative control solutions (provided by the shown in Table IV. For the methamphetamine reagents, an ethyl manufacturer) were used to compare the cross-reactivity of the group on the amine nitrogen impeded but did not eliminate compounds tested to amphetamine or methamphetamine. Stan- binding and the hydroxy group at the 4 position also did not dard curves at 0, 500, 1,000, and 1,500 ng/mL analyte were eliminate binding. Addition of a second methyl group to the analyzed with each batch of analogs tested. Each rack of 20 tubes amine nitrogen substantially decreased binding as demonstrated also contained duplicate standards at the 0- and l,OOO-ng/mL by the N,N-dimethyl-MDA data. Methoxy groups at various levels for evaluation of assay drift or decanting irregularities. positions on the ring also significantly decreased binding. Results Concentrations of the various amphetamine analogs were an- of the other compounds tested with the methamphetamine alyzed in quadruplicate. Average CPM determinations of repli- reagents are shown in Table V. cates were used to determine percent cross-reactivity. The data show the L-isomers of amphetamine and metham- Data analysis. Quantitations were based on comparison of phetamine to be significantly less reactive than the D-isomers. the mean CPM of four replicates for each compound at each These results have important implications in the interpretation concentration against a log-logit curve derived from five of data. In some countries, including the U.S., Vicks Inhalers replicates of standards at 0,500, 1,000, and 1,500 ng/mL of contain 50 mg of L-methamphetamine (t-desoxyephedrine). n-arnphetamine for the amphetamine assay and D-metham- With the advent of RIA reagents that are targeted specifically phetamine for the methamphetamine assay. Any assay rack that to n-methamphetamine, the potential for a positive result from showed values for the 0- or l,OOO-ng/mL standards that were not within acceptable limits was repeated. Table I. Typical Precision Data for OPC Amphetamine and Methamphetamine
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