Uncertainty Evaluation of the Analysis of 11-Nor-9-carboxy- 9 -tetrahydrocannabinol in Human Urine by GC/MS
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1 k v r 52 r 6 480~487 (2008) Yakhak Hoeji Vol. 52, No. 6 GC/MS w d y sƒ ½ # Á Á Á Á *Á½ *Á, *w x t (Received October 6, 2008; Revised December 2, 2008) Uncertainty Evaluation of the Analysis of 11-Nor-9-carboxy- 9 -tetrahydrocannabinol in Human Urine by GC/MS Jin Young Kim #, Jae Chul Jeong, SungIll Suh, Yong Jun Suh, Jeong Jik Lee*, Jong Sang Kim* and Moon Kyo In Drug Analysis Laboratory, Supreme Prosecutors' Office, 706, Banporo, Seocho-gu, Seoul , Korea *Department of Quality Management, Korea Institute of Construction Materials, Seoul , Korea Abstract We described an estimation of measurement uncertainty in quantitative analysis of 11-nor-9-carboxy- 9 -tetrahydrocannabinol (THCCOOH), the major metabolite of 9 -tetrahydrocannabinol, in urine sample by solid-phase extraction (SPE) and GC/MS detection. The analytical results were compared and the different contributions to the uncertainty were evaluated. Inter-day and inter-person validation were performed using statistical analysis of several indicative factors. Measurement uncertainty associated with target analyte in real forensic samples was estimated using quality control (QC) data. Traceability of measurement was established through traceable standards, calibrated volumetric glassware and volume measuring device. The major factors of contribution to combined standard uncertainty, were calibration linearity, inter-day repeatability and inter-person reproducibility, while those associated with preparation of analytical standards and sampling volume were not so important considering the degree of contribution. Relative combined standard uncertainties associated with the described method was 12.05% for THCCOOH. Keywords uncertainty of measurement, urinanalysis, GC/MS, 11-nor-9-carboxy-delta 9-tetrahydrocannabinol (Cannabis sativa L.) dk ˆ (methamphetamine) pp l q p n k p. 1) p l p(high), d (happy smoke), rpp pl, p. ml (hemp)pv k n (marijuana). l m v p ee (hashishi)p. n l 1960 t t p k r 1970 rp l 1975 p m l s p ' k l ' s p m } o l. l 420s p p p sq, p l 60l sp p (cannabinoid) p. # l p rql (r ) (Žd) ( ) paxus@spo.go.kr p t 9 -tetrahydrocannabinol(thc)p qn p p tn p, ~ rp ~ 11-nor-9- carboxy- 9 -tetrahydrocannabinol(thccooh) (Fig. 1). 2-4) q THCCOOH l l l Ž r t v n p. 5) p rp t THCCOOH l 4~8e 4t r v pp p k r p. 6,7) l ~ p l lp ll Žr rp l e n tn. v v rp e l l p r rp v. p ee l r(method validation) r er e m v (QC) e p r (precision)m r (accuracy) p e ˆ l. p p p n p e r, e q, nkrs e l p m, q l m pq p m 480
2 t ~ p r 481 Fig. 1 Chemical structures of delta-9-tetrahydrocannabinol and its metabolite(11-nor-9-carboxy-tetrahydrocannabinol). e p p on v m. l r (uncertainty of measurement) 8) p r p n kl p l p e r rp q rp p. l l ll pp o rl r m. n t ~ rl l m p t p np p }k l, e(measurand)p r, np r p t (standard uncertainty), t (combined standard uncertainty) q (expanded uncertainty) m. p l r e k 95%p e l r p sq o m. 9) np l r e m npp m p eˆ n m. x t v THCCOOHp 1ml n p o (vial)l 0.1 mg/ml, t v THCCOOH-d 3 p 1ml n p o l 10 µg/ml rs r p Cerilliant l p m. rl n n ekp p J. T. Baker l p m. o ~ ekp N,O-bis(trimethylsilyl)trifluoroacetamide/1% trimethylchlorosilane(bstfa/1% TMCS) Alltech p m. ~ l n v Oasis MCX(60 mg, 3 ml) Waters l p m. tnkp p t vp methanoll l rp 10, 1, 0.1 µg/ml e sr mp, n r v -20 o Cl m.»» tnkp sr o p Brand p n d (10 ml)m p Eppendorf p (1000 µl)p n mp, e l n e p kp r o p Eppendorf p (1000 µl)p n m. r} rp q q p ƒ p Rapid Trace SPE workstationp n l ~ (solid-phase extraction, SPE)p m. l n q Agilent Technologies 6890 Gas Chromatograph(GC)l 5973 Mass Selective Detector l GC/MS n m. p DB-5MS(25m 0.25mm I.D., 0.25 µm film thickness, J&W Scientific, USA) n m. m }p 200 o Cl 1 oveˆ, 30 o C/minp 290 o C v m m, l d 35 o C/min p 300 o C v m de 2 ove. tp m op m 250 o Cm 280 o C r m. n ~ p o p 0.7 ml/minp r m, tp p e(splitless mode)p purge-on timep 0.75 p r m. e Agilent Technologies 7683 q tp q (autosampler) n l q l tp m o 7o v k 2 o k q ~p r p l npqp p l n e n m. k p n v kp p p } l s e n m. l n s e n p n r v -20 o Cl m. e p ' t e '(SPO-DRUG-QA-04, 2006) l r l ee m. 5) e 3mlp 1mlj 3 l e ( mm) l p, 1 µg/ml p t v 45 µl ~ m. 10 M KOH nk 200 µl pn l ml 30, k p ~ l ph 4 sr m. ~ n v o ˆm 1mlm v 1ml 2ml/minp tl. vl e 2ml/minp t, v 2mlm 4ml tl } m. e p vp r vl n p ethyl acetate 3 ml 2ml/minp tl p THCCOOH p m. n kp pr k (30 kpa) m (45 o C) v l v eˆ, q l o ~ ek BSTFA/1% TMCS 50 µl l 70 o Cl 15 o ~ pp e. e mp p t 1µl GC/MSl tp l m (Fig. 2). r o tl sq l o Vol. 52, No. 6, 2008
3 482 vmërq~ë dpë ntëprvë s Ëp t ~p 5 ng/ml, e m p p }, r kp l r Š m. p (inter-day) r p e q 4p l r mp, e q (inter-person) r p e q l r m. y d Fig. 2 Preparation procedures of urine sample for the analysis of THCCOOH. r mp, 3 v p THCCOOH tnk(10, 1, 0.1 µg/ml)p s e l ~ l (calibration curve)p q m. l l THCCOOHp r o 2.0~40 ng/ml r l tnkp ~ l 4 p p r(calibration point)l e rs m. l l THCCOOH-d 3 p ˆml l 1µg/ml rs tnk 45 µl l p p e m p p } l m. s r} e t 1µl GC/MSl tp l mp, p q m. t (QC) s e 3mll THCCOOH tnkp ~ l l THCCOOHp rp e p (urine sampling), rr p r} GC/MS q pn rp. l THCCOOHp rl n e rl, rl n tnkp, p pn l p r p, rp r p ˆ l p e ql p rp 5 v n p. l THCCOOH p npp ep p p r m. C i =x i Ëf vol' Ëf std Ëf cal' Ëf variation Ëf person (1) C i : l r THCCOOHp xi : y i -b/m, q l r f vol' : } p p f std : tnkp p f cal' : p v l p p Fig. 3 Uncertainty factors associated with measurement results. J. Pharm. Soc. Korea
4 t ~ p r 483 f variation : QC e p r p f person : e q r p THCCOOHp e (1)l np p Fig. 3l e l e mp, p n p. f vol' p t THCCOOHp kp e l n p. f cal' p pn l r p rl n p, f std tnkp m l n p. f variation p er lqp p p np( vp m, rp )l p n p, f person e q l r np( redš, q )l p n p. f variation f person v (QC) e l r m l ˆ l. 10,11) l s p e l oo t vp ~ t p n p f r t r} l p mr, n p v, e e k e qp sq e p r p r m. 12) š GUM(Guide to the Expression of Uncertainty in Measurement)p r 8) np (p p e )p r, p np Ž k, p p n t, er e l r p p n l m ˆ 4 p. v r l npp n t, t l t. t l e tl pq(coverage factor, k) l q, ˆ. 13) v d y sƒ p r l e r rl (pipette)p (u pipet' ) npp l p. q~p r r q n m. r r 95%p e l (k=2) mlmp, p t (u pipet' ) mlpl. r 1ml l p t (u r pipet' ) 0.003pl. 1ml p n l e 3mlp r 1mlj 3 r p t m. 1mlj 3 rl p t (u r vol' ) e(2)l rn, mlpp k p l. u r vol' = u r pipet' = n 3 (n : 1, 2,..., i) e r rp o qo (ν eff ) np t p qo e(3)p Welch-Satterthwaite equationl rn l p ( )m. ν eff = u 4 c u i ---- ν i (ν eff : the effective degrees of freedom, u c : the combined standard uncertainty, u i : the individual standard uncertainties, ν i : the degrees of freedom) t y sƒ tnkp nl tnk(stock standard solution, S)p rs l n. tnk sr rp tnkp, n n d (volumetric flask) p npp. tnkp 10 1 tnk(1st working standard solution, W1)p rs rp p o l r tnkp t m. n t vp pv p l t (u purity(s) ) t (u r purity(s) ) l Table Il r m. t vp l rn t v kp l B p pn l m, t t l m. tnk l n n d l p n n d q~p, m l p. d q~p r r 95%p e l (k=2) ml t (u cert' ) ml pp k pl. m l p t Ž} Table I Uncertainty of purity of THCCOOH Analyte Concentration range (mg/ml) Standard uncertainty (u purity(s) ) (2) (3) Relative standard uncertainty (u r purity(s) ) THCCOOH ± Vol. 52, No. 6, 2008
5 484 vmërq~ë dpë ntëprvë s Ëp Table II Relative standard uncertainties of diluted standard solutions (working solutions) and standard preparation Analyte Conc' (mg/ml) u r purity(s) u r flask u r pipet' u r std(w1) u r std(w2) u r std(w3) u r std THCCOOH ml/ o Cp e e m s p 20±5 o Cp t (u temp' ) mlpp k pl. rž l n d pn rl p t (u flask ) mlpl, o qo (ν eff ) l. t (u r flask ) e(4)l rn l p p m. tnk sr rp t e(9)p rn l plp p p Table IIl ˆ l. u r flask = u vol' V 1 (4) (u flask = ( u cert' ) 2 +u ( temp' ) 2, V 1 =10 ml) 1 tnk(w1)p sr rl l m p pq t vp m n d l p v pq e(5)l rn l t (u r std(w1) ) m, p Table IIl r m. u r std W1 ( ) = ( u r purity( S) ) 2 +u ( r flask ) 2 2 tnk(w2)p 1 tnkp e 10 l r s. W2 rse m 1 tnkp, l n n d pq, qll p pq v e(6)l rn l 2 tnkp t (u r std(w2) ) m. p p e(7)l rn l 3 tnk (W3)l t l Table IIl m. (5) u r std( W2 ( ) 2 +u ( r flask ) 2 +u ( r std( W1) ) 2 ) = u r pipet' (6) u r std( W3 ( ) 2 +u ( r flask ) 2 +u ( r std( W2) ) 2 ) = u r pipet' tnk l n l p n r r 95%p e l (k=2) mlp t (u pipet' ) ml p k p. t (u r pipet' ) e(8)l rn l pp k pl, o qo (ν eff ) m. (7) u r pipet' = u pipet' V 2 (8) (V 2 =1 ml) tnk rsm ržp l Fig. 4 Representative SIM (selected ion monitoring) chromatogram obtained from spiked urine sample containing 15 ng/ml of THCCOOH. J. Pharm. Soc. Korea
6 t ~ p r 485 u r std = ( u r std( W1) ) 2 +u ( r std( W2) ) 2 +u ( r std( W3) ) 2 QC w y sƒ redšp, vp m (matrix effect), rp q p l pl Š lk p rl t l p QC e n l QC e p r (precision) redšp r pql (u precision ) r p. 14) e l 5.0 ng/ml p QC e ˆ l m. p e q p (inter-day) r rp o 4p l r mp p e q pl rp rp p lv redš q p n QC e l r m m. Fig. 4 ~ t vp QC e p Š p. po 15) r ep e(10) p, inter-day inter-person l t e(11)m p r lv. e(11) THCCOOHl p Table III Standard uncertainty of inter-day repeatability No. THCCOOH (5.0 ng/ml) 1st day 2nd day 3rd day 4th day Mean Variance Standard uncertainty (u variation ) Relative standard uncertainty (u r variation ) Table IV Standard uncertainty of inter-person reproducibility No. THCCOOH (5.0 ng/ml) 1st person 2nd person 3rd person Mean Variance Standard uncertainty (u person ) Relative standard uncertainty (u r person ) (9) QC e p r p e q r pl t m plp, p QC e p r p e q r pl t (u r variation, u r person ) pl (Table III, IV). y=µ+a i +ε ij (10) (µ: expected value of random variable x, A i : error between the groups, ε ij : measurement error) u precision =s A = M between-m within (11) n 0 (M between : sum of squares between groups, M within : sum of squares within groups, n 0 : number of measurements) w y sƒ p v p r p tn npp. p rp r r(1 e)l p p r p ee l r (R 2 ) p f p. p p o r ep p p ˆ p. y i =(mëx i )+b (12) (y i : ratio of the analyte area to internal standard area, x i : analyte concentration, m: slope, b: intercept of the calibration curve) p 4 (2, 10, 20, 40 ng/ml)p tnkp 2 l q m (Table V). p p q rp rr s p l r p m. THCCOOHp p r , n , y-r 0.009p p ˆ l. er nqp e THCCOOH p l rn l 2 l lp ng/mlpl. r p q l p pp el p p. 16) u cal' = s y ---- m p n x-x --+ ( )2 S xx (13) (x i =(y i -b/m), p: number of measurements to determine x i, n: number of measurements for the calibration, d i =y i -(mëx i )-b, d = d i /n, s y =( ( d i -d) 2 )/(n-2), x = x i /n, S xx = ( x i -x )2 ) Table Vp p e(13)l rn l llv l t (u r cal' ) plp Table VIl ˆ l. Vol. 52, No. 6, 2008
7 486 vmërq~ë dpë ntëprvë s Ëp Table V Calculations for least-squares analysis 2 No. x i y i x i Ëy i x i d i d i 2 d i - d (d i - d ) 2 s xx Sum ( )2 x i = y i-b , d i =mx i -b, d i = d i , S xx = x i -x m n Table VI Detailed estimation of uncertainty contributions in the results of THCCOOH analysis in human urine samples Uncertainty factors Relative standard uncertainty THCCOOH Effective degrees of freedom, ν eff Coverage factor, k Degree of contribution (%) Sample volume (u r vol' ) Standard solution (u r std ) Run control (precision, u r variation ) Inter-person (precision, u r person ) Calibration curve (u r cal' ) Relative combined standard uncertainty (u r (C)) Relative expanded uncertainty (U r (E)) Uncertainty was quantified for a single measurement of drug user urine sample. Coverage factor, k, was obtained from the Student's t-distribution corresponding to the calculated effective degrees of freedom of relative combined standard uncertainty using a confidence level of 95.45%. y y q o l p np l t Table VIl r m. pqp p qo o qo, k 95% e tl p pq k r mp, p t llv t (u r (C)) 0.058pl. p p pn l ll v q (U r (E)) pp ep pn l m. U r (E)=kËu r (C) (14) e(14)p q (U r (E)) 0.12p lp, p Table VIl m. l THCCOOHp r p 95% e l l (11.53±1.39) ng/ml(k=2.1, e t k 95%)pl. Table VIl GC/MS pn t ~ p r srp s Ër m. e s l e p k np p l p. l l t THCCOOH r l l npp p l r p sq o e p f p vp r rp ˆ q m. r v l ˆ p l m. nk r p p n p p e r, p l n p r, p t rp k p. ržp l t t, pq(k) l s q m. er lqp l THCCOOHp r p 11.53pl, q 0.12m. r p k 95%p e l pq k=2.1p l (11.53±1.39) ng/ml(k=2.1, e t k 95%)plp, THCCOOHp l 12.05%m. l l Š npp 5 v e p, tnkp rs, p rp, e q rp q GC/MS p v pl. r rp l 5 v np t e q rp q, p J. Pharm. Soc. Korea
8 t ~ p r 487 rp, p v l p n q m p nppp k pl. ~w, e q r l p e q,, qv p pl p p p. e q r v o, e v v p e q tl pp p Ž. w, p rp l p e q r l p m t p pp p t p rp r p p k l rn k r pp p. pp p v l p vp p p vp m l p p Ž, vp (separation resolution) ˆ (selectivity)p eˆp f pr r p Ž. p e l r e l me m np p m p e ˆ n mrp. l p pn l l l p l r p }p rn l Œkl pp THCCOOH p r p sq o rp r m rl p p. l r o (MEST)m q (KOSEF)p rl l (M N )l p p vo ld. š x 1) ~ : 2007 k t. ~ kësv t, p. 16 (2008). 2) Wall, M. E., Brine, D. R., Brine, G. A., Pitt, C. G., Freudenthal, R. I. and Christensen, H. D. : Isolation, structure, and biological activity of several metabolites of delta-9-tetrahydrocannabinol. J. Am. Chem. Soc. 92(11), 3466 (1970). 3) Agurell, S., Nilsson, I. M. and Widman, M. : In Marihuana Chemistry, Biochemistry and Cellular Effects, Nahas, G. (ed.). Springer-Verlag: New York, p. 141 (1976). 4) U.S. Department of Heath and Human Servies : NIDA Research Monograph 42, National Institute on Drug Abuse, Rockville, MD, USA, p. 43 (1982). 5) rq~, vm, p, ros : ~ GC/MS pn t ~(THCCOOH). v 19(5), 441 (2006). 6) Mason, A. P. and McBay A. J. : Cannabis: pharmacology and interpretation of effects. J. Forensic Sci. 30(3), 615 (1985). 7) Vandevenne, M., Vandenbussche, H. and Verstraete, A. : Detection time of drugs of abuse in urine. Acta Clin. Belg. 55(6), 323 (2000). 8) Guide to the expression of uncertainty in measurement (GUM). ISO/IEC Guide 98 (1995). 9) EURACHEM/CITAC : Quantifying Uncertainty in Analytical Measurement 2nd ed., EURACHEM/CITAC Guide CG 4 (2000). 10) nv : r p (II) - r (GUM)l. v 13(3), 49A (2000). 11) Sin, Della W. M., Wong, Y. C., Mak, C. Y., Sze, S. T. and Yao, W. Y. : Determination of five phenolic antioxidants in edible oils: Method validation and estimation of measurement uncertainty. J. Food Compos. Anal. 19, 784 (2006). 12) r,, nv, qo : k e t pmep l. v 16(6), 475 (2003). 13) s, s : r p rp o ržl l. ƒ r 8(4), 167 (2002). 14) White, G. H. and Farrance, I. : Uncertainty of measurement in quantitative medical testing: A laboratory implementation guide. Clin. Biochem. Rev. 25(iv), 207 (2004). 15) rm, sv, e, rpv : SPSS 14.0 q, s l, t p. 219 (2008). 16) Harris, D. C. : Quantitative Chemical Analysis 3rd ed., W. H. Freeman and Company, New York, p. 63 (1991). Vol. 52, No. 6, 2008
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