Borova, Viola L.

Pistos, Constantinos

Thomaidis, Nikolaos S.

Digital Repository of Hellenic Managing Authority of the Operational Programme &quot;Education and Lifelong Learning&quot; (EDULLL)

9/11/20141Optimization, validation, and application of LC-(QqQ)MS/MS for the determination and occurrence of new drugs of abuse in wastewater samples Viola L. Borova Constantinos Pistos and Nikolaos S. ThomaidisNational and KapodistrianUNIVERSITY OF ATHENSFaculty of ChemistryWhat are “New Designer Drugs”Designer Drugs:§ Synthetically changed natural substances§ Completely designed molecular structures§ Psychotropic effectsNew Designer Psychotropic Drugs:§ Drug alternatives§ Optimized effects of already existing drugsØ Higher binding affinity with CB1, greater potency and adverseeffects and longer duration of action§ Not covered in most countries by controlled substancestatutesØ avoid detection and legal consequences§ “Spice” drugs (smoking mixtures, herbal mixtures), bathsalts on the recreational drug use marketINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSI I9/11/20142Classes of New Designer DrugsPhenylalkylamines• Beta-keto (mephedrone, butylone (bk-MBDB), methylone (bk-MDMA)Piperazines• Phenylpiperazine (DCPP, mCPP, MeOPP, pCPP, TFMPP)• Benzylpiprazine (BZP, MBZP, DBZP, MDBZP)Synthetic Cannabinoids• JWH cannabinoids (John W. Huffman), • (JWH 018, JWH 073 aminoalkylindoles series and more than 400 cannabinoids)• CP47, 497 (From Pfizer, cyclohexylphenolseries) (analog CP47,497 and homologue C6,C7,C8,C9) Pyrrolidinophenones• Derivatives (PPP, MPPP, MPHP, MOPPP, MDPPP)INTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSI ImephedroneBZPJWH 018, JWH 073 CP47,497MPPP9/11/20143New Designer Drugs… a new class of emerging organic contaminants§Not currently covered by existing water quality regulations§Not investigated or little §Newly identified or previously unrecognized§Lack of environmental data§Lack of analytical methods in wastewater§Large volume of consumption and production§Potential threats to ecosystems and human (limited information)  Drug consumptionDrug and metabolites excretionWastewater treatment Plant (WWTP)Released into the aquatic environmentUncompleteRemovalEstimate Consumption in communitiesINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSI IANALYTICAL METHODOLOGYThermo Scientific Quantum AccessLC- (QqQ) MS/MS -ESIINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSI9/11/20144TARGET COMPOUNDSCompounds M. Formula MW LogP pKaJWH-018naphthalen-1-yl-(1-pentyl-1H-indol-3-yl) methanone/ JWH-018 D9C24H23NO 341.5 6.51 -JWH-073(1-Butyl-1H-indol-3-yl)(1-naphthyl)methanonC23H21NO 327.4 6.07 -CP47,4972- [(1R,3S)-3-hydroxycyclohexyl]-5-(2-methyloctan-2-yl)phenolC21H34O2 318.5 6.17 -Mephedrone / Mephedrone D3C11H15NO 177.2 2.12 8.69Benzylpiperazine/BZP D7C11H16N2 176.2 1.38 9.59MPPP4'-Methyl-α-pyrrolidinopropiophenoneC14H19NO 217.3 2.91 -ONC H 3ONC H 3OHCH3CH3CH 3OHCH 3ONCH3CH3ONHCH3 CH3NNHINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSIMethod Development and Optimization of MS/MSCompounds [Μ+H]+ Product Ions (collision energy)TubeLens (V)ESIJWH-018 342.1 155.0 (25V)127.0 (44V) 81.8 +JWH-018D9 351.1155.0 (26V)127.0 (45V) 80.1 +JWH-073 328.1 154.9 (25V)127.0 (43V) 76.3 +CP47,497 317.2 298.9 (24V)244.7 (34V) 99.1 -Mephedrone 178.1 160.0 (12V)145.0 (19V) 48.1 +MephedroneD3 181.1163.0 (12V)148.0 (21V) 49.0 +BZP 177.1 91.2 (28V)65.3 (40V) 62.5 +BZP D7 184.1 98.2 (27V)70.3 (40V) 66.3 +MPPP 218.1 119.1 (24V)146.9 (18V) 61.1 +Positive IonizationProbe: C (0.5/1.5)Spray Voltage: 3500 VSheath gas: 30 a.u. Aux gas: 10 a.u.Temp:270°CNegativeIonizationProbe: C (0.5/1.5)Spray Voltage: 2500 VSheath gas: 20 a.u. Aux gas: 10 a.u.Temp:300°CINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONS§ PTI IZATI  F S/ S9/11/20145Comparison of stationary phases  Stationary phases: Atlantis T3 (C18) (Waters), XSelect (C18) (Waters) & PFP (Phenomenex)RT: 0.00 - 30.000 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30Time (min)05101520253035404550556065707580859095100Relative Abundance2.963.3120.1619.162.1918.7820.6013.51 27.973.97 17.7314.084.67 24.6823.6412.775.98 9.190.60NL:1.26E7TIC  MS std_100ppb_test2_atlantisT3TIC Atlantis T3RT: 0.00 - 30.000 2 4 6 8 10 12 14 16 18 20 22 24 26 28Time (min)05101520253035404550556065707580859095100Relative Abundance15.6016.245.652.9710.0113.5117.656.419.55 11.12 17.92 23.2422.05 26.8924.24 27.771.00NL:1.04E7TIC  MS std_100ppb_test1_PFPTIC PFP R T: 0 .0 0 - 30 .0 00 2 4 6 8 10 12 14 16 18 20 2 2 24 2 6 2 8 30Ti me  (m i n)0510152025303540455055606570758085909510 0Relative Abundance4.411 9.3 32 0.3 61 8.8 35.532.6013 .6 11 3.3 81 2.086.6 3 1 7.1210 .8 4 2 5.542 0.7 5 26 .182 5.220.7 4N L:9 .31 E6T IC   M S  s td _1 00 ppb_ tes t1_ XSE LE C T_T3TIC XSelect T3vCompounds with –NH2 or –NH-presented higher asymmetry(fronting) on C18 columnvXselect and Atlantis T3 sufferfrom peak shape issues and do notprovide good separation of thecompoundsvPFP: excellent peak shape, goodresolution and separation in shorttime with excellent MS sensitivityINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONS§ I I I   Mobile Phase   Positive H2O (0.2% formic acid)MeOH μL/min0.00 60 40 1003.00 60 40 15015.00 0.0 100 10025.00 0.0 100 10025.50 60 40 10030.00 60 40 100Negative MeOH ACN μL/min0.00 90 10 1003.00 90 10 10015.00 90 10 100JWH 018, JWH 073, Mephedrone, Benzylpiperazine, MPPPCP47, 497INTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONS§ I I I   9/11/20146Effect of the organic modifier   RT:0.00 - 30.000 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30Time (min)05101520253035404550556065707580859095100Relative AbundanceRT: 16.64AA: 195005RT: 16.72AA: 101987RT: 16.58AA: 84573RT: 10.62AA: 102635RT: 10.71AA: 87754RT: 10.52AA: 86732RT: 15.94AA: 36636RT: 10.81AA: 66363RT: 10.84AA: 61290RT: 10.46AA: 60925RT: 15.93AA: 27648RT: 16.55AA: 42775RT: 16.80AA: 37556RT: 10.42AA: 47555RT: 10.98AA: 41233RT: 10.39AA: 39313RT: 11.05AA: 32790RT: 9.57AA: 15404RT: 11.19AA: 21596RT: 16.86AA: 13736RT: 9.35AA: 9603 RT: 19.50AA: 7214RT: 14.33AA: 6833 RT: 20.42AA: 3647RT: 9.18AA: 3242 RT: 22.48AA: 1565RT: 1.86AA: 2035RT: 28.32AA: 1274RT: 3.01AA: 686RT: 5.49AA: 551RT: 24.61AA: 1182RT: 15.86AA: 4024NL:2.77E6TIC  MS  ICIS STD_NEW_DRUGS_50ppb_2_001FART:0.0  - 30.000 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30Time (min)05101520253035404550556065707580859095100Relative AbundanceRT: 16.85AA: 233538RT: 7.22AA: 162110RT: 16.93AA: 96849RT: 7.37AA: 114213RT: 16.76AA: 94783RT: 16.93AA: 79612RT: 7.10AA: 93175RT: 7.47AA: 77415RT: 4.59AA: 47422RT: 7.51AA: 64821RT: 7.08AA: 69092RT: 12.42AA: 31385RT: 12.32AA: 31252RT: 16.97AA: 48918RT: 4.68AA: 51714RT: 7.57AA: 52269RT: 4.72AA: 47845RT: 12.60AA: 22886 RT: 17.00AA: 26965RT: 12.18AA: 19329RT: 7.68AA: 34849RT: 4.47AA: 18764RT: 12.81AA: 13598RT: 7.81AA: 22105RT: 4.44AA: 11203RT: 16.00AA: 9232RT: 4.97AA: 8884 RT: 17.07AA: 11789RT: 4.40AA: 6902RT: 8.16AA: 9967RT: 12.01AA: 4277RT: 4.33AA: 2499RT: 17.41AA: 2286RT: 2.47AA: 855RT: 29.99AA: 401RT: 19.72AA: 638RT: 21.88AA: 260RT: 24.19AA: 216RT: 26.67AA: 200NL:3.27E6TIC  MS  ICIS STD_NEW_DRUGS_50ppb_2_005FART:0.00 - 30.000 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30Time (min)05101520253035404550556065707580859095100Relative AbundanceRT: 16.87AA: 313861RT: 6.28AA: 191716RT: 16.97AA: 123287RT: 6.38AA: 146182RT: 3.50AA: 70901 RT: 6.47AA: 99666RT: 16.77AA: 80731RT: 6.16AA: 96122RT: 17.00AA: 69178RT: 6.15AA: 89894RT: 11.06AA: 42396RT: 6.54AA: 74049RT: 3.58AA: 74410RT: 11.25AA: 33969RT: 3.68AA: 47948RT: 6.64AA: 51772RT: 17.03AA: 39728RT: 6.68AA: 42010RT: 11.47AA: 19721RT: 17.07AA: 23125RT: 6.85AA: 24843RT: 3.79AA: 26250RT: 11.66AA: 12410 RT: 14.41AA: 9804RT: 10.82AA: 9271RT: 3.36AA: 6683RT: 7.16AA: 10951RT: 17.17AA: 8552RT: 4.05AA: 9094RT: 3.33AA: 3605RT: 1.34AA: 672RT: 19.29AA: 966RT: 16.04AA: 437RT: 29.64AA: 481RT: 21.66AA: 297RT: 24.20AA: 185RT: 25.64AA: 147NL:4.04E6TIC  MS  ICIS STD_NEW_DRUGS_50ppb_2_01FAR T: 0 .0 0 - 30 .000 2 4 6 8 10 12 14 16 18 20 22 24 26 28Tim e (m i n)051 01 52 02 53 03 54 04 55 05 56 06 57 07 58 08 59 09 51 00Relative AbundanceR T: 16.87AA: 38 66 38R T : 5 .55AA: 18 775 4R T : 1 6.9 9AA: 13 583 5R T : 2.8 6AA: 89 19 0R T: 5.70AA: 1 18 135R T : 16.77AA: 92 48 8R T: 16 .76AA: 7 82 48R T: 5.4 3AA: 9 169 1R T: 2.9 3AA: 9 270 3 R T : 1 0.22AA: 43 90 0R T : 5 .8 1AA: 75 356R T: 10 .43AA: 3 099 7R T: 17 .0 6AA: 4 75 05R T: 5.9 3AA: 4 802 1R T: 2.7 7AA: 20 42 2R T: 17 .10AA: 2 709 3R T: 10.61AA: 18 60 2R T : 6 .1 5AA: 22 569 R T: 14 .46AA: 9 17 5R T: 17 .2 2AA: 1 10 11R T: 10 .99AA: 7 43 4R T : 2 .7 3AA: 60 38R T : 5.2 8AA: 92 33R T: 6.98AA: 3 91 9R T: 2.7 0AA: 1 888 R T : 29.88AA: 56 6R T: 16 .0 5AA: 1 44 34R T: 16 .0 6AA: 4 94R T: 19 .71AA: 5 35R T: 23 .1 1AA: 3 55R T : 2 4.7 3AA: 24 1N L:5.5 4E6TIC   MS  IC IS STD _ N EW_D R U GS_50 ppb _2 _02FART: 0.00 - 30.000102030405060708090100Relative AbundanceRT: 19.50MA: 7903192SN: 12420.0119.2920.1819.0920.3720.5220.8621.0521.3822.6728.3223.2824.2526.37 28.5318.381.86 10.489.043.04 5.39 8.316.84 11.260.66 14.00 16.87RT: 19.50NL: 7.68E4Base Peak m/z= 118.6 0-119.60 F: + c ESI SRM ms2 218.100 [118.900- 119.300, 146.8 00-147.200]  MS STD_ NEW_DRUGS_50ppb_2_001FANL: 6.91E4TIC 0.01 FA% MPPPt=19.5minArea=8*106TIC 0.05 FA%TIC 0.1 FA%TIC 0.2 FA%RT: 0.00 - 30.000102030405060708090100Relative AbundanceRT: 12.36MA: 15250118SN: 56812.2712.6013.2713.4913.8615.10 16.453.30 18.57 28.4611.418.246.555.71 9.09 23.05 25.341.22 20.68 26.17RT: 12.36NL: 3.37E5Base Peak m/z= 118.60-119.60 F: + c ESI SRM ms2 218.100 [118.900-119.300, 146.800-147.200] MS STD_NEW_DRUGS_50ppb_2_005FANL: 3.36E5MPPPt=12.3minArea=15*106RT: 0.00 - 30.000102030405060708090100Relative AbundanceRT: 11.06MA: 17468088SN: 124611.5411.8512.1412.69 13.74 15.768.48 17.94 19.77 24.395.48 6.19 21.139.16 28.334.400.51 2.91 26.06RT: 11.13NL: 4.58E5Base Peak m/z= 118.60-119.60 F: + c ESI SRM ms2 218.100 [118.900-119.300, 146.800-147.200] MS STD_NEW_DRUGS_50ppb_2_01FANL: 4.41E5MPPPt=11.1minArea=17*106RT: 0.00 - 30.000102030405060708090100Relative AbundanceRT: 10.26MA: 18572640SN: 162311.3712.04 13.23 15.01 16.37 29.006.38 7.694.27 20.073.50 21.490.33 23.57 26.8224.39RT: 10.22NL: 4.73E5Bas e Peak m/z= 118.60-119.60 F: + c ESI SRM ms2 218.100 [118.900-119.300, 146.800-147.200]  MS STD_NEW_DRUGS_50ppb_2_02FANL: 4.34E5MPPPt=10.2minArea=18*106MephedroneMephedroneMephedroneMephedroneRT: 9.75MA: 8850663SN: 3419.65 9.9310.4310.7211.48 12.67 14.046.60 8.64RT: 9.790 .00  - 30.00RT: 2.95MA: 11608026SN: 17654.07 5 .40 7 .191 .95BZPBZPBZPBZPJWH 018JWH 018JWH 018JWH 018JWH 073JWH 073JWH 073JWH 073INTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONS§ I I I   Sample preparation- Comparison SPE  020406080100120BZP Mephedrone JWH 018 JWH 073 MPPP CP47Absolute Recovery %Recoveries with different sorbents (n=5)STRATA XSTRATA XCISOLUTE C18EVOLUTE ABNISOLUTE C18and STRATA XCINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONS9/11/20147Sample preparation  1. Wastewater samples were filtered on Glass fiber filters 2. 50 mL of filtrated sample were adjusted at a value of pH 2.5 with HCl (1 M)3. Internal deuterated standards of the compounds were added to all samples4. SPE (STRATA-X/ISOLUTE C18, STATA-XC)Reconstitution :500 μL of 40% MeOH and 60% ultra purified water with 0.05% v/v formic acidLC-MS/MSINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSValidation for wastewater samples  Linear rangeμg/LCorr. CoefficientR2methodLOD  [ng/L]AbsoluteRecovery % (n=5)RSD%(n=5)BZP 1 – 100 0.9993 4.8 29.0 14.8Mephedrone 1 – 100 0.9994 0.3 100 3.7MPPP 1 – 100 0.9994 0.6 99.0 4.2CP47,497 1 – 100 0.9991 37 97.0 15.2JWH 018 1 – 100 0.9991 1.4 40.0 8.3JWH 073 1 – 100 0.9992 0.8 42.0 15.3INTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONS9/11/20148Wastewater Samples from WWTP SantoriniSampling23/07/2013- 29/07/2013INTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSAPPLICATION IN REAL INFLUENTWASTEWATERSAMPLESüMediterranean climateüHigh anthropogenic impactüPopulation: 10500 inhabitantsüFlow rate: 1500 m3/dayWastewater Samples from WWTP Santorini0102030405060708090100%Frequency of detection INTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSAPPLICATION IN REAL INFLUENTWASTEWATERSAMPLES•RANGES:•BZP → <LOD – 17.8 ng/L•Mephedrone → 1.5 – 4.0 ng/L•MPPP → <LOD ng/L•CP47→ 179 – 1469 ng/L•JWH 018→ <LOD – 2.2 ng/L•JWH 073→ <LOD – 1.0 ng/L9/11/20149Wastewater Samples from WWTP SantoriniINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSAPPLICATION IN REAL INFLUENTWASTEWATERSAMPLES0.0200.0400.0600.0800.01000.01200.01400.01600.023/7/13 24/7/13 25/7/13 26/7/13 27/7/13 28/7/13 29/7/13Conc. (ng/L)CP 47MPPPMEPHEDRONEJWH 073JWH 018BZPLevels in influent wastewater of FiraWastewater Samples from WWTP SantoriniINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSAPPLICATION IN REAL INFLUENTWASTEWATERSAMPLES0.05.010.015.020.025.030.023/7/13 24/7/13 25/7/13 26/7/13 27/7/13 28/7/13 29/7/13Conc. (ng/L)CP 47MPPPMEPHEDRONEJWH 073JWH 018BZPLevels in influent wastewater of Fira9/11/201410CONCLUSIONSü Development and validation of a novel method for new designer drugs in wastewater by LC-MS/MS üInvestigation of their occurrence in a WWTP in Santorini Islandü5 out of the 6 compounds were detected at least in one day üCP47 was detected for the first time in influent wastewaterüNot any special trend among the days was observed for mephedrone and CP47INTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSC CL SI SFuture PerspectivesüIntegration into one multi-analyte method which provides the elution of all the compounds with one cartridge üIdentification of their transformation productsüApplication of the method in the WWTP of AthensINTRODUCTIONANALYTICAL METHODOLOGY§OPTIMIZATION OF MS/MS§OPTIMIZATION OF HPLC§OPTIMIZATION OF SPEMETHOD VALIDATIONAPPLICATION IN REAL INFLUENT WASTEWATER SAMPLESCONCLUSIONSCONCLUSIONS9/11/201411Questions?http://trams.chem.uoa.gr/Contact information: vborova@chem.uoa.grntho@chem.uoa.grThis research has been co-financed by the European Union and Greek national funds through the Operational Program "Education and Lifelong Learning" of the National Strategic Reference Framework (NSRF)

Optimization, validation, and application of LC-(QqQ)MS/MS for the determination and occurrence of new drugs of abuse in wastewater samples

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Optimization, validation, and application of LC-(QqQ)MS/MS for the determination and occurrence of new drugs of abuse in wastewater samples

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Digital Repository of Hellenic Managing Authority of the Operational Programme "Education and Lifelong Learning" (EDULLL)

Optimization, validation, and application of LC-(QqQ)MS/MS for the determination and occurrence of new drugs of abuse in wastewater samples

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Digital Repository of Hellenic Managing Authority of the Operational Programme &quot;Education and Lifelong Learning&quot; (EDULLL)

Digital Repository of Hellenic Managing Authority of the Operational Programme "Education and Lifelong Learning" (EDULLL)