Simultaneous determination of amphetamine derivatives and norketamine in hair by GC-MS/MS
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1 Printed in the Republic of Korea "/"-:5*$"- 4$*&/$& 5&$)/0-0(: Vol. 22, No. 3, , 2009 ($.4.4 w rk fk ½ Á yáš Á Á Á Simultaneous determination of amphetamine derivatives and norketamine in hair by GC-MS/MS Jin Young Kim, Soon Ho Shin, Beom Jun Ko, Jae Cheol Chung, Yong Jun Suh and Moon Kyo In Drug Analysis Laboratory, Supreme Prosecutors' Office, 706 Banporo, Seocho-gu, Seoul , Korea (Received April 26, 2009; Accepted May 18, 2009) : GC-MS/MS w rk 4 fk y w» w w. m w,» w, k w š HFBA yw GC-MS/MS w w. w ü w ùkü, w k, y y w. š (r ) ùkü š w ng/mg w z %. ü (intra-day) (inter-day) y % ùkü 10.7% w» (20% w) ü ùkü. y w rk s ng/ mg rk ng/mg. Abstract: A gas chromatography-tandem mass spectrometry (GC-MS/MS) method was developed and validated for simultaneous determination of amphetamine derivatives and norketamine in human hair. Preparation of hair involves external decontamination, mechanical pulverization, incubation and extraction prior to instrumental analysis. The samples were derivatized using heptafluorobutyric anhydride, and analyzed by GC-MS/MS. The linear ranges were ng/mg for the analytes except for 3,4-methylenedioxyamphetamine, with good coefficients of determination (r 2 >0.998). The intra-day and inter-day precisions were within 10.7% and 8.5%, respectively. The intra-day and inter-day accuracies were between -1.6 and 17.0% and -2.6 and 10.5%, respectively. The limits of detections for each analyte were lower than ng/mg, while recoveries were %. When the method was applied to hair samples obtained from suspected drug abusers, the concentrations in hair samples were ng/mg for methamphetamine and ng/mg for amphetamine. Key words : Amphetamine derivatives, norketamine, GC-MS/MS, hair Corresponding author Phone : +82-(0) Fax : +82-(0) paxus@spo.go.kr 210
2 GC-MS/MS w rk fk 211 rk sw ü û ƒ rk (MA, methamphetamine), (MDMA, 3,4-methylenedioxymethamphetamine), (MDA, 3,4-methylenedioxyamphetamine), rl (phentermine). w w ƒ wš wš yƒz ƒ» g w ù n. ü ƒ û MA w j ü rk (AP, amphetamine) x. w MDMA MA l z k MDA. l (MDMA) 2 w MDMA m ƒ š fk (ketamine), MDA, er (caffeine) yw m. p fk mw f 3 k (NKT, norketamine) x š w y w» w. fk MAù 4 MDMA j ù û ƒw w š. ü û ƒ 5,6 š wz û ƒ j x f y š rw w š y. w, x,. x 7 w, x y 1 ü y. l w ¼ w w» y w, w (sectional analysis) mw y w. 8,9 w. (decontamination), (pulverization), (incubation), (extraction)»» (instrumental analysis). ƒ ƒ š n, ƒ w l j» w, (ball) w, ky (bead) w w ù w ƒ w j» w 10 sw» (matrix) w.» ü sw w z w» w š (solid-phase extraction) (liquid-liquid extraction) ù ƒ. w» w. w w z w ü q w. rk 5 M hydrochloric acid (HCl)/methanol (1:20, v/v), 0.25 M methanolic HCl, acetone, methanol » l w e w ƒƒ w x v w. j» z w w ùkú».» j m v- (GC-MS), j m 14,17,18 v» w yw w (LC-MS/MS) š w w w w d 22 š. ü û ƒ w MA, AP, MDMA, MDA, NKT w š rw y w š w» l w z w, ƒ y ww GC- MS/MS w wwš w.» t ü t ƒƒ 1 ml (vial) 1 mg/ml MA, AP, MDMA, MDA, NKT 1mL 100 µg/ml MA-d 11, AP-d 8, MDMA-d 5, x Vol. 22, No. 3, 2009
3 212 ½ Á yáš Á Á Á š» 6 l p (2.8 mm diameter) ¼ 2 ml p w. w Whatman PTFE (polytetrafluoroethylene) vl(13 mm diameter, 0.2 µm pore size) w š, w Caliper Lifescience TurboVap LV» w. Fig. 1. Chemical structures of amphetamine derivatives and norketamine, and internal standards used. MDA-d 5, NKT-d 4 Cerilliant w (Fig. 1). k, m J. T. Baker HPLC w š Milli-Q water purification system m w 3 w. y heptafluorobutyric anhydride (HFBA)» Acros Organics l w. š x 5 t v k g w, w» ¾ -20 C þ o w.» w» v Bertin Technologies Precellys 24» w»» x»» Agilent Technologies 6890 Gas Chromatograph Waters Quattro micro GC tandem mass spectrometer w. DB-5MS (30 m 0.25 mm I.D., 0.25 µm film thickness, J&W Scientific, USA) w, 90 C o 0.5 k z w 25 C/min o 150 C¾ o jš 1.5 k z, 15 C/min å o 210 C¾ g o 1.5 w z 40 C/min o 310 C¾ o jš 1.1 w.» ƒƒ 260 C o 280 C o w.» x 1.1 ml/min, splitless mode purge-on time 0.35 w. Agilent Technologies»(7683B automatic liquid sampler) w 1 µl w.» y (source) 200 o C š y EI (electron impact) MRM (multiple reaction monitoring) w w. MS/MS fragmentation w» š w ù collision cell ü 2.75±1.0 mtorr w. product ion» w collision energy 5-15 ev ¾ y gš precursor ion l p product ion w ƒƒ wù l w l 3 26 ¾» QC k (blank hair) w w. Analytical Science & Technology
4 GC-MS/MS w rk fk mg x ( mm) z, 5 ml 2z, acetone 5 ml 2z kw w. ³ 1 jš v Bertin Technologies»(Precellys 24) w 5000 rpm 90 w. ƒ ¼ p ü t (0.3 µg/mg) 50 µl k 1 ml ƒw z w (50 C) o 1 q w. d PTFE vl(13 mm diameter, 0.2 µm pore size) w z, w (4.5 psi) (40 C)w» w o g. š m 50 µl HFBA 50 µl ƒw 50 C o 30 g. þƒ k z yw» w š g. š ethyl acetate 50 µl 1 µl GC-MS/MS w w. t š t t 1 mg/ml MA, AP, MDMA, MDA, NKT k 100, 10, 1, 0.1 µg/ml w t w. w ey ü t MA-d 11, AP-d 8, MDMA-d 5, MDA-d 5, NKT-d 4 k w 0.3 µg/ml ü t w. š w» w MDA w 0.05, 0.15, 0.2, 0.5, 1, 5, 10, 20 ng/mg wš, ü t 1.5 ng/mg w. MDA 0.05, 0.15, 0.2, 0.5, 1, 5 ng/ mg w. w w z j m l vj y wš, ü t vj w vj ƒ š š w. š y l z w» w j» w v w. j»ƒ t ƒw z. z» z (matrix effect) w w w wì f j» w z» w v w.» ƒ w ƒ š. (ball) (bead) w w ƒ j l j»ƒ ƒ w w z w w». w 24 ƒ ƒ w Precellys 24» w 2.8 mm l p 6 ƒ ¼ 2 ml p rpm Fig. 2. Pictures of the blank hair before and after pulverization. Vol. 22, No. 3, 2009
5 214 ½ Á yáš Á Á Á Fig. 3. Particle size distribution of pulverized hair powder w. j» p ywš w š z y w j» Cilas 1064 Particle Size Analyzer w d w s³ 123 µm. z Fig. 2 ùkü z j» s Fig. 3 t w. s š e w ¼, Ì š w w w w. w w yw z w k w 0.25 M methanolic HCl k wš w. ù sw k yw w j m w. w w š. w e y j q (swelling property) ù š k w. 23 w g z d w vl(syringe filter) w. PTFE m ƒ w j»ƒ 0.2 µm w vl w w» z x w. j m rp mw t ƒ w w rk fk 5 y wš w y w. GC»» w 10 ü š w j m Fig. 4 ùkü. Fig. 1 yw r ü»(-nh) swwš GC ü ù ƒ. w j» w» yw y v w. rk y y(acylation) trifluoroacetic anhydride (TFAA), pentafluoropropionic anhydride (PFPA), heptafluorobutyric anhydride (HFBA) w yw. p AP MA w HFBA 24 TFAA PFPA k z w x y w. 25 y e EI yw MRM w w Analytical Science & Technology
6 GC-MS/MS w rk fk 215 Fig. 4. GC-MS/MS chromatogram for HFB derivatives of 5 analytes and corresponding internal standards, including (A) drug-free hair, (B) drug-fortified hair at the concentration of 0.5 ng/mg for each analyte, and (C) drug user hair samples.. ƒƒ rp (mass spectrum)» (base ion) p precursor ion w, collision energy ƒw product ion l w. AP MA precursor ion + [M-C 7 H 7 ] m/z ƒ š collision cell š» AP m/z , MA m/z 210 w. MDA precursor ion + [M-C 6 H 5 F 7 NO] m/z 135, MDMA precursor ion + [M-C 8 H 7 O 2 ] m/z 254ƒ š MDA product ion m/z 77, MDMA product ion m/z 210 w. NKT precursor ion molecular ion [M] ion + HCl m/z 384 ƒ š product ion m/z 171. ü t MRM transition collision energy Table 1 w. z y š w» w k ƒ ng/mg (MA, AP, MDMA, NKT) ng/mg (MDA) ƒ t ƒw y GC-MS/MS w ü t w š w. rk fk 5 w š r 2 =0.998 ü w ùkü. w (limit of detection, LOD) k (N, noise) ƒw (S, signal) ü sw ùkü. w 6 w 6 k l t r w S/N ƒ 3 w, w 10 w š w ng/mg ùký ¾ ƒ w (Table 2). x z (recovery)» w xw. t ƒw e z ü t ƒw»» ww.» ƒw (amount) t ƒwš ü t ƒw»» w. š» w š w š w w z w.» z (%) e z z e t 100 w. (0.3, 3, 15 ng/mg) d AP, MA, MDMA, NKT (0.3, 3 ng/mg) d MDA z % (Table 3). x y sƒw» w ƒ AP, MA, MDMA, NKT 0.3, 5, 15 ng/mg, MDA 0.3, 3 ng/mg k t ƒw w d w. ü(intra-day, n=3) (inter-day, n=4) (% RSD) 10.7% 8.5% w yw š, ü y (% bias) % % x x. û (0.3 ng/mg) 20% ü y ùkü, (AP, MA, MDMA, NKT: 3, 15 ng/ Vol. 22, No. 3, 2009
7 216 ½ Á yáš Á Á Á Table 1. GC-MS/MS information of 5 analytes and internal standards used as their HFB derivatives No Analyte Molecular weight Retention time (min) MRM transitions precusor ion (m/z) product ion (m/z) CE (ev) 1 AP * AP-d MA MA-d MDA MDA-d MDMA MDMA-d NKT NKT-d * Underlined transitions were used for quantification Table 2. Sensitivity and calibration results Analyte Calibration range (ng/mg) Slope y-intercept Linearity a (r 2 ) LOD b (ng/mg) LOQ c (ng/mg) AP MA MDA MDMA NKT a Linearity is described by the coefficient of determination (r 2 ) for the calibration curve. b Limit of detection (LOD) and c limit of quantification (LOQ) were based on the concentration corresponding to 3 and 10 standard deviations from the mean of six replicates of QC samples. mg, MDA: 3 ng/mg) ü ùkü w z x ww (Table 3). 26 ü w l 26 ¾ (n=15) w MA ng/mg ùkü MA AP ng/mg ùkü. AP MA ùkü ùkü. MA ƒ ng/mg AP ƒ w w ù kü. (parent drug) y q» w ƒ w. w rk fk 5 wš yw w š y w. z w» l w w z wš z w k w ƒ Analytical Science & Technology
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