Detection of Methadone, Methadone Metabolites, and Other Illicit Drugs of Abuse in Hair of Methadone-Treatment Subjects,*

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1 [ TechncalNote Detecton of Methadone, Methadone Metaboltes, and Other llct Drugs of Abuse n Har of Methadone-Treatment Subjects,* Bruce A. Godberger 1,*, Abeer G. Darraj z,*, Yale H. Caplan 3, and Edward J. Cone 4 Z Department of Pathology, mmunology, and Laboratory Medcne, Unversty of Florda College of Medcne, P.O. Box , Ganes vlle, Florda ; 2Department of Medcal and Research Technology, Unversty of Maryland School of Medcne; 3Natonal Scentfc Servces, 3411 Phlps Dflve, Baltmore, Maryland ; and 4Addcton Research Center, Natonal nsttute on Drug Abuse, P.O. Box 5180, Baltmore, Maryland [Abstract [ The dsposton of methadone, ts metaboltes, and other llct drugs of abuse was nvestgated n head har samples collected from heron users (N = 20) enrolled n an outpatent detoxfcaton study. Har samples were assayed for methadone, methadone prmary metabolte (2-ethyldene-l,5-dmethyl-3,3- dphenylpyrroldne, EDDP), methadone secondary metabolte (2-ethyl-5-methyl-3,3-dphenylpyrrolne, EMDP), cocane, phencycldne, heron, and 6-acetylmorphne. Har samples were cut, washed, and ncubated n methanol. The methanolc har wash and ncubaton fractons were purfed wth sold-phase extracton and assayed by gas chromatography-mass spectrometry. Methadone, methadone metaboltes, cocane, and phencycldne were assayed quanttatvely, and other drugs were measured qualtatvely. The number of postve results and the correspondng concentraton ranges were as follows: methadone, ng/mg (N = 18); EDDP, trace (N = 13); EMDP, trace (N = 1); cocane, 0->40 ng/mg (N = 14); phencycldne, ng/mg (N = 2); heron, postve (N = 3); and 6-acetylmorphne, postve (N = 4). These data suggest that testng har for methadone, methadone metaboltes, and other llct drugs of abuse may be useful to drug-treatment specalsts as a means of verfyng drug-use hstory, montorng complance, and provdng a broad measure of drug exposure. ntroducton Methadone s a synthetc opod agonst wth pharmacologc actvty, duraton of acton, and potency smlar to morphne. Methadone s commonly used for short-term detoxfcaton and mantenance treatment of narcotc addcton (1). Methadone s metabolzed by mono- and d-n-demethylaton, wth spontaneous cyclzaton to 2-ethyldene-l,5- * Presented at the 2nd nternatonal Meetng on Clncal and Forensc Aspects of Har Analyss, Genova, taly, 1994 * Author to whom correspondence should be addressed. * Current address unknown, dmethyl-3,3-dphenylpyrroldne (EDDP) and 2-ethyl-5- methyl-3,3-dphenylpyrrolne (EMDP). Methadone s metabolzed further by hydroxylaton to methadol, followed by N-demethylaton to normethadol. Hydroxylaton, followed by glucuronde conjugaton of methadone, EDDP, and EMDP also occurs (2). Urne s the preferred specmen for substance-abuse testng. However, recent studes have demonstrated that har analyss for the presence of abused drugs provdes valuable nformaton regardng long-term drug use (3). As a part of an ongong program n assay development for llct drugs n har, we developed a method for the detecton and measurement of methadone, methadone metaboltes, and other commonly abused llct drugs. Ths paper descrbes a gas chromatographc-mass spectrometrc (GC-MS) assay for methadone, EDDP, EMDP, cocane, phencycldne, heron, and 6-acetylmorphne n har obtaned from heron users enrolled n a methadone outpatent detoxfcaton study. Materals and Methods Chemcals and materals Methadone, EDDP, EMDP, cocane, and 6-acetylmorphne were obtaned from Radan Corporaton LLC (Austn, TX). Heron and phencycldne were obtaned from USP (Rockvlle, MD). Mepvcane was obtaned from Alltech-Appled Scence (State College, PAL All chemcals were reagent-grade qualty. Sold-phase extracton (SPE) cartrdges (ZSDAU020) and fltraton reservors (RFV02F4P) were purchased from Unted Chemcal Technologes (Horsham, PA). Subjects Har samples were obtaned from 20 subjects who had been enrolled n a 180-day outpatent mantenance and detoxfcaton study at the Addcton Research Center n Baltmore, MD. 526 Reproducton (photocopyng) of edtoral content of ths journal s prohbted wthout publsher's permsson,

2 Durng the study, subjects receved ether 20 mg or 60 mg of methadone. Upon completon, the subjects were asked to provde har trmmngs from the entre scalp area for study of drag-usage patterns. Samples were collected 3-12 months after detoxfcaton. All studes were approved by the nsttutonal Revew Board for Human Subjects Research at the Francs Scott Table. Subject Characterstcs Subject Race Gender Methadone dose (mg/day) 1 Afrcod F* 60 2 Afrcod M 60 3 Caucasod M 60 4 Caucasod F 60 5 Caucasod M 60 6 Afrcod F 20 7 Caucasod F 60 8 Caucasod M 60 9 Caucasod M Caucasod F Caucasod F Caucasod F Caucasod F Caucasod M Caucasod M Afrcod F Afrcod M Afrcod M Caucasod F Caucasod F 20 * Abbrevatons: M, male and F, female. Key Medcal Center, Baltmore, MD. The study was conducted under the gudelnes for the protecton of human subjects, and each volunteer provded nformed consent. Table summarzes subject characterstcs. Control (.e., drug-free) har samples were obtaned from ndvduals who were unlkely to be drug users. Har wash and ncubaton procedures Approxmately 25 mg of har was placed n a fltraton column and cut nto approxmately 1-mm segments wth surgcal scssors. Methanol (1 ml) was added, and the sample was vortex mxed for 30 s. The wash fracton was collected and evaporated at 40~ under a stream of argon gas. After washng, methanol (1 ml) and mepvcane (100 ng) were added. A small strrng bar was placed n the reservor, the top of the reservor was sealed wth paraflm, and the reservor was ncubated for 18 h n a 37~ water bath equpped wth a magnetc strrer. Followng ncubaton, the methanol was removed and evaporated at 40~ under a stream of argon gas. Extracton of har samples Methanolc wash and ncubaton fractons were assayed separately by SPE. Samples were prepared by mxng wth 2 ml deonzed water and 2 ml 0.1M phosphate buffer (ph 6.0). The SPE cartrdges were condtoned wth methanol (2 x 2 ml), deonzed water (2 x 2 ml), and 0.1M phosphate buffer (2 ml, ph 6.0). Samples were added to the SPE cartrdges, followed by deonzed water (2 ml), 0.1M acetc acd (1 ml), and methanol (2 ml). The cartrdges were asprated to dryness for 5 mn and treated wth a soluton of methylene chlorde/2-propanol/ ammonum hydroxde (80:20:2, %v/v/v; 3 x 1 ml). Extracts Table. Results of Har Analyses for Methadone, Methadone Metaboltes, and Other llct Drugs of Abuse* Subject Methadone EDD ~ EMDP Cocane Phencycldne Heron 6-Acetylmorphne 1 0 (0) 0 (0) 0 (0) 39.7 (7.2) 0 (0) postve (0) postve (0) (5.4) trace (0) trace (0) 33.1 (2.4) 0 (0) 0 (0) 0 (0) (9.5) trace (0) 0 (0) 0 (0) 0 (0) 0 (0) 0 (0) 4 trace (0) 0 (0) 0 (0) 3.7 (0) 0 (0) 0 (0) 0 (0) (12.9) trace (0) 0 (0) 0 (0) 0 (0) 0 (0) 0 (0) (5.2) trace (0) 0 (0) >40 (4.7) 0 (0) postve (0) postve (0) (0) trace (0) 0 (0) 0 (0) 0 (0) 0 (0) 0 (0) (0) trace (0) 0 (0) 0 (0) 0 (0) 0 (0) 0 (0) (0) trace (0) 0 (0) 6.0 (0) 0 (0) 0 (0) 0 (0) 10 0 (0) 0 (0) 0 (0) 2.7 (0) 0 (0) 0 (0) 0 (0) (0) trace (0) 0 (0) 0 (0) 1.1 (0) 0 (0) 0 (0) 12 trace (0) 0 (0) 0 (0) 0 (0) 0 (0) 0 (0) 0 (0) (0) trace (0) 0 (0) 1.8 (0) 0 (0) 0 (0) 0 (0) 14 trace (0) 0 (0) 0 (0) 7.0 (0) 0 (0) 0 (0) 0 (0) (4.9) trace (0) 0 (0) 1.8 (0) 0 (0) 0 (0) 0 (0) (0) 0 (0) 0 (0) >40 (4.2) 0 (0) postve (0) postve (0) (12.0) trace (0) 0 (0) 17.6 (0) 0 (0) 0 (0) 0 (0) 18 trace (0) trace (0) 0 (0) 5.7 (0) 0 (0) 0 (0) 0 (0) (13.4) trace (0) 0 (0) 1.7 (0) 1.5 (0.8) 0 (0) 0 (0) (0) 0 (0) 0 (0) 16.7 (0) 0 (0) 0 (0) postve (0) * Results are expressed as concentraton (ng/mg) of drug n extracts. Result of wash fractons are ndcated for each specmen n parenthess. Trace amounts are ndcated where responses were lower than or equal to the lmt of quanttaton, but the sgnal-to-nose rato was 5 or greater. Heron and 6-acetylmorphne were reported as postve when the sgnal-to-nose rato was 5 or greater. Abbrevatons: EDDP, 2..ethyldene-l,S-dmethyl-3,3-dphenylpyrroldne and EMDP, 2-ethyl-5-methyl-3,3-dphenylpyrrolne. 527

3 were collected n concal centrfuge glass tubes and evaporated at 50~ under argon gas. SPE extracts were reconsttuted n methanol (50 pl). The extractons were performed wth vacuum-asssted eluton wth a vacuum flow rate of approxmately 1-2 ml/mn. GC-MS assay GC-MS analyses were performed wth a Hewlett-Packard 5890A seres GC and 7673A automatc lqud sampler nterfaced wth a Hewlett-Packard 5971A mass selectve detector (MSD). A crosslnked 95% dmethyl 5% dphenyl polysloxane capllary column (30 m 25-ram.d., 0.25-pro flm thckness, Restek, Bellefonte, PA) and a 2-mm.d. slanzed fused-slca A Standard PCP, & - xl0 xl "~1.S. ~ B Drug-free control xl.s." x2 xl0.~. Methadone lner wth a slanzed glass wool plug were used. njectons (2 pl) were made n the spltless mode wth a purge tme of 0.50 ran. Ultra-pure grade helum was used as the carrer gas at a flow rate of 1.2 ml/mn. The njecton port and transfer lne temperatures were 250~ and 290~ respectvely. The ntal oven temperature was 150~ held for 1 mn, ncreased to 300~ at 20~ and held for 6 mn. The MSD was operated n the selected on montorng mode. ons were montored at a dwell tme of 20 ms for each compound n the followng eluton order (ons noted n parenthess were used for quanttaton): phencycldne, m/z 91, (200), 242; EMDP, rn/z 179, 193, (208); EDDP, m/z 220, 262, (277); mepvcane, m/z (98); methadone, m/z (72), 91,165; cocane, m/z 82, (182), 303; and 6-acetylmorphne/heron, m/z 215, 268, 327, 369. The mass on defect of all quanttatve ons for standards and nternal standards were determned wth an MS resoluton of 0.1 anu. The GC-MS was tuned wth perfluorotrbutylamne wth ons rn/z 69, 219, and 502, and the electron multpler was operated at 600 ev relatve to the tune value. Mantenance of the GC-MS ncluded clppng of the GC column and replacement of the njector septum, lner, and gold-plated seal. Methadone, EDDP, EMDP, cocane, and phencycldne were assayed n a quanttatve mode wth mepvcane as an nternal standard; the lmt of quanttaton was 0.5 ng/mg. Heron and 6-acetylmorphne were measured qualtatvely (postve result = S/N = 5). Standard curves were constructed wth a mnmum of fve standard concentratons per analyte. Analytes were dentfed based upon comparson of retenton tme and on abundance ratos. Results C Subject L xl xl 11"-- EDDF 9 Methadone o e.o Tme (mn) Fgure 1. Characterstc selected on montorng recordngs of extracts of a har standard fortfed wth 2 ng/mg of methadone, EDDP, EMDP, cocane, and phencycldne (A), drug-free control har (B) and subject 6's har (C). Chromatograms were constructed wth the followng ons: phencycldne, m/z 200; EMDP, m/z 208; EDDP, m/z 277; mepvcane (S), m/z 98; methadone, m/z 72; and cocane, m/z 182. = An assay was developed for the detecton of methadone, EDDP, EMDP, cocane, phencycldne, heron, and 6-acetylmorphne n har. Har samples were cut, washed, and ncubated n methanol. The methanolc wash and ncubaton fractons were extracted usng SPE and assayed by GC-MS operated n the selected on montorng mode. Quanttaton was based upon nternal standardzaton usng mepvcane. Methadone, EDDP, EMDP, cocane, and phencycldne were assayed quanttatvely, and heron and 6-acetylmorphne were measured qualtatvely. Standard curves for methadone, EDDP, EMDP, cocane, and phencycldne were lnear over a range of ng/mg of har. The lmt of senstvty (S/N -- 5)was less than 0.5 ng/mg of har for all analytes. Fgure 1 llustrates characterstc selected on montorng recordngs of extracts of a har standard fortfed wth 2 ng/mg of methadone, EDDP, EMDP, cocane, and phencycldne (Fgure 1A); drug-free control har (Fgure 1B); and subject 6's har (Fgure 1C). Twenty har samples from heron users enrolled n a methadone outpatent detoxfcaton study and 10 samples from drug-free control subjects were assayed by GC-MS for methadone, EDDP, EMDP, cocane, phencycldne, heron, and 6-acetylmorphne. Quanttatve results of har wash and ncubaton fractons are shown n Table. Methadone was 528

4 present n 18 samples n concentratons rangng from 1.0 to 15.0 ng/mg. EDDP was present n trace amounts n 13 samples. Cocane was present n 14 samples n concentratons rangng from 1.7 to 40 ng/mg. Phencycldne was present n two samples n concentratons rangng from 1.1 to 1.5 ng/mg. Heron and 6-acetylmorphne were present n three and four subjects, respectvely. Results of analyses of the control subjects' har samples were negatve for methadone, EDDP, EMDP, cocane, phencycldne, heron, and 6-acetylmorphne. Analyss of the wash fractons from the heron users' har samples revealed postve results for methadone and cocane n 35 and 20% of the analyses, respectvely, n concentratons rangng from 4.9 to 13.4 and 2.4 to 7.2 ng/mg, respectvely. Wash fractons were negatve for EDDP and EMDP, 6-acetylmorphne, and heron. The wash fracton of subject 19 was postve for phencycldne. Dscusson A procedure employng SPE combned wth GC-MS analyss was developed for the assay of methadone, EDDP, EMDP, cocane, phencycldne, heron, and 6-acetylmorphne n har. Quanttaton of methadone and ts metaboltes was performed to determne the pattern of dsposton n har collected from known heron users partcpatng n an outpatent methadone mantenance and detoxfcaton program. Methadone and ts prmary metabolte (EDDP) were detected n 18 (90%) and 13 (65%) of the samples, respectvely. Cocane (N = 14), phencycldne (N = 2), heron (.N = 3), and 6-acetylmorphne (N = 4) were also dentfed. Methadone, cocane, and/or phencycldne were also detected n about one-thrd of the wash fractons. t s unclear to what extent ths wash procedure dfferentates external contamnaton from drug embedded n har; however, t seems lkely that washng preferentally removes external contamnaton. For methadone, external contamnaton could have occurred from exposure to sweat or sebum secretons. Because both cocane and phencycldne are frequently smoked, the sources of these drugs may also nclude envronmental contamnaton. Fnally, although consderable amounts of drug were present n several wash fractons at concentratons exceedng the ncubaton fracton, the loss of drug nto the washes dd not appear to affect our ablty to detect drug n the ncubaton fracton. Methadone has been prevously dentfed n har of methadone users usng mmunoassay and chromatographc procedures. The results of several methadone studes n humans (4-7) are summarzed n Table. The relatonshp of methadone dose, race, and gender versus the concentraton of methadone n har was evaluated and sgnfcant dfferences were not apparent (p < 0.05). Because har trmmngs were assayed, rather than har strands, t s not surprsng that a dose-concentraton relatonshp was not evdent. However, the concentraton of cocane n har of the Afrcod group was greater than the concentraton n the Caucasod group. These fndngs are consstent wth those of a prevous study (8). The lmted number of subjects wth postve cocane test results n ths study precluded the use of statstcal analyses to determne sgnfcance. Heron-dependent subjects are often transferred to methadone for mantenance and detoxfcaton. t s essental to have an accurate measure of current and past drug-use hstory to provde clncally relevant pharmacologc and psychologc therapy. Analyss of har samples for drug content, ncludng commonly abused drugs, provdes a unque means of obtanng an overall assessment of the subject's drug-takng behavor. n concluson, these data suggest that testng har for methadone, methadone metaboltes, and other llct drugs of abuse may be useful to drug-treatment specalsts as a means of verfyng drug-use hstory, montorng complance, and provdng a broad measure of drug exposure. References 1. T. Resne and G. Pasternak. Opod analgescs and antagonsts. n Goodman & Glman's The Pharmacologcal Bass of Therapeutcs, 9th ed. J.G. Hardman, L.E. Lmbrd, RB. Molnoff, R.W. Ruddon, and A.G. Glman, Eds. McGraw-Hll, New York, NY, 1996, pp R.C. Baselt and R.H. Cravey. Dsposton of Toxc Drugs and Chemcals n Man, 4th ed. Chemcal Toxcology nsttute, Foster Cty, CA, 1995, pp Table. Summary of Methadone Har Studes* Study Methodology N Methadone (ng/mg) EDDP t (ng/mg) Balabanova and Wolf (4) Marsh et al. (5) Wlkns et al. (6) Kntz et al. (7) Present study Sem-quanttatve radommunoassay 13 Head: not assayed 10 Axllary: Pubc: Quanttatve radommunoassay not assayed Postve chemcal onzaton on trap MS LC-on spray MS (R*) (R) (Sw (S) GC-MS trace * Unless otherwse noted, all specmens were head har. * EDDP, 2-ethyldene-l,5-dmethyl-3,3-dphenylpyrroldne. (R)-Enantomer of methadone. w (S)-Enantomer of methadone. 529

5 3. Drug Testng n Har, R Kntz, Ed. CRC Press, nc., Boca Raton, FL, S. Balabanova and H.U. Wolf. Methadone concentratons n human har of the head, axllary and pubc har. Z. Rechtsmed. 102" (1989). 5. A. Marsh, M.B. Evans, and J. Strang. Radommunoassay of drugs of abuse n har. Part 2: The determnaton of methadone n the har of known drug users. J. Pharm. Bomed. Anal. 13: (1995). 6. D.G. Wlkns, RR. Nagasawa, S.R Gyg, R.L. Foltz, and D.E. Rollns. Quanttatve analyss of methadone and two major metaboltes n har by postve chemcal onzaton on trap mass spectrometry. J. Anal. Toxcol. 20: (1996). 7. P. Kntz, H.P. Eser, A. Tracqu, M. Moeller, V. Crmele, and P. Mangn. Enantoselectve separaton of methadone and ts man metabolte n human har by lqud chromatography/on spraymass spectrometry. J. Forensc Sc. 42: (1997). 8. E.J. Cone. W.D. Darwn, and W.-L. Wang. The occurrence of cocane, heron and metaboltes n har of drug abusers. Forensc Sc. nt. 63:55-68 (1993). Manuscrpt receved Aprl 6, 1998; revson receved June 3,

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