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Appendix 2 – Analytical methodologies

Overview

Urine samples were analysed using three methodologies.

The first methodology (General Screen) was designed to cover a wide range of analytes () and was used for all analytes other than the synthetic (SCRAs). The analyte coverage included a broad range of commonly prescribed drugs including over the counter , commonly misused drugs and metabolites of many of the compounds too. This approach provided a very powerful drug screening tool to investigate drug use/misuse before and whilst in prison.

The second methodology (SCRA Screen) was specifically designed for SCRAs and targets only those compounds. This was a very sensitive methodology with a method capability of sub 100pg/ml for over 600 SCRAs and their metabolites.

Both methodologies utilised full scan high resolution accurate mass LCMS technologies that allowed a non-targeted approach to data acquisition and the ability to retrospectively review data. The non-targeted approach to data acquisition effectively means that the analyte coverage of the data acquisition was unlimited. The only limiting factors were related to the chemical nature of the analyte being looked for. The analyte must extract in the sample preparation process; it must chromatograph and it must ionise under the conditions used by the mass spectrometer interface. The final limiting factor was presence in the data processing database.

The subsequent study of negative MDT samples across the North West and London and the South East used a GCMS methodology for anabolic steroids in addition to the General and SCRA screens.

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Sample Preparation

General Screen

A 2ml portion of the sample was dispensed from the primary container. A 1ml aliquot of 1M pH 6.3 phosphate buffer containing D3 glucuronide, D6 , D10 and d3 EDDP was added and the mixture hydrolysed overnight at 45 oC using beta glucuronidase derived from Helix pomatia.

The sample was then centrifuged prior to extraction using a solid phase extraction (SPE) methodology on an Agilent Nexus reversed phase polymer sorbent. The resulting elution from the cartridge was taken to dryness in a centrifugal evaporation system, reconstituted in LCMS mobile phase and submitted for analysis by full scan high resolution accurate mass LCMS

SCRA Screen

A 2ml portion of the urine sample was dispensed from the primary container. A 1ml aliquot of 1M pH 4.7 acetate buffer containing D5 hydroxypentyl JWH-018 was added and the mixture hydrolysed overnight at 45 oC using beta glucuronidase derived from Helix pomatia.

The pH of the sample was then adjusted to pH 12 and a liquid/liquid extraction performed for 20 minutes. The sample was then centrifuged and the organic layer removed and taken to dryness in a centrifugal evaporation system, reconstituted in LCMS mobile phase and submitted for analysis by full scan high resolution accurate mass LCMS.

Anabolic Steroid Screen (phase 2 of study)

A 2.5ml portion of the urine sample was dispensed from the primary container. A 0.5ml aliquot of 2.5M pH 6.8 acetate buffer containing d3 morphine glucuronide and various internal markers was added and the mixture hydrolysed overnight at 37 oC using beta glucuronidase derived from E. coli.

The sample was extracted using a double SPE methodology. The first stage was performed on a Phenomenex Strata XC mixed mode cation exchange polymeric sorbent. A first elution contained neutral anabolic steroids and this was further purified using an anion exchange polymeric sorbent. The resulting eluent was taken to dryness in a centrifugal evaporator and reconstituted in a derivatising mixture before transfer to a GCMS vial. The capped vial was heated at 80C for 2 hours to form enol trimethylsilyl derivatives. The sample was then submitted for analysis by GCMS.

A second elution was performed on the mixed mode cation exchange cartridge to remove basic compounds. This was combined with part of the first elution and then taken to drynesss in a centrifugal evaporation system. The sample was then reconstituted in LCMS mobile phase and submitted for analysis by full scan high resolution accurate mass LCMS using the general screen instrument conditions below.

Instrumental analysis

General Screen

Samples were analysed on an Accela UPLC system interfaced to an LTQ Orbitrap Discovery High Resolution Accurate Mass mass spectrometer from Thermo operating in positive ion electrospray mode. Data were acquired in full scan mode operating at a mass resolution of

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30,000 across a mass range of 85-600 amu.. In addition, a second scan event using ‘in source fragmentation’ at a setting of 100V was acquired at a mass resolution of 15,000 across a scan range of 50-500 amu. Acquired data files were processed using Thermo Toxfinder software against a database containing NPS compounds augmented with compounds specifically requested by NOMS. The content of this database is listed in the database section at the end of the methods section.

SCRA Screen

Samples were analysed on an XRS UPLC system interfaced to a Q Exactive Focus High Resolution Accurate Mass mass spectrometer from Thermo operating in heated positive ion electrospray mode. Data were acquired in full scan mode operating at a mass resolution of 70,000 across a mass range of 240-550 amu.. In addition, a second scan event using ‘all ion fragmentation’ was performed with a stepped HCD setting of 37,45 at a mass resolution of 35,000 across a scan range of 95-500 amu.

GCMS Screen for anabolic steroids

Sample were analysed on an Agilent 5973 MSD GCMS instrument operating in windowed selected ion monitoring (SIM) mode. A SIM/SCAN acquisition method was used allowing targeted screening for ‘expected’ compounds and concurrent coverage for unexpected compounds in the same analysis.

Data Processing

General Screen

Acquired data files were processed using Thermo Toxfinder software against a database containing NPS compounds augmented with compounds specifically requested by NOMS. The content of this database is listed in the database section at the end of the methods section.

SCRA Screen

Acquired data files were processed using Thermo Toxfinder software against a database containing SCRA compounds. The content of this database is listed in the database section at the end of the methods section.

Data processing summary

Data processing is based on the ability of the instrumentation to measure masses very accurately. Compounds with the same apparent molecular weight but different empirical formulae will actually have different accurate masses. This gives a much higher degree of selectivity when processing data, as mass windows of +/- 2 mDa (0.002 Da) can be used. The data processing software uses the accurate masses of the database analytes, the chromatographic retention time (Rt) of the database analytes, accurate mass qualifier ions where appropriate/available and a comparison of theoretical (derived from elemental composition) against actual isotope pattern. Where the search criteria are met, an identification is made. Manual data review is then performed to verify the findings.

Where the identity of a finding was in doubt, further analysis by MS/MS techniques was performed to either confirm or rule out a finding.

GCMS Anabolic Steroid Screen

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The screening methodology for anabolic steroids by GCMS is a targeted test. Data processing is through the generation of hardcopy reports with extracted ion chromatograms for each anabolic steroid and associated metabolites. Data are reviewed manually by experienced/ trained laboratory personnel.

Method capability

General Screen – capability determined for major findings.

As the analysis was qualitative and not quantitative, cut off levels were not used in the testing/reporting. The variations in sensitivity between analytes were due primarily to differences in extraction recovery, mass spectrometer ionisation efficiency and the analytical signal to noise for each analyte. Some compounds, had less interference from background material than others, hence better signal to noise, leading to better method capabilities.

A comparison is given below between MDT screening cut-offs and LGC screening capabilities for the major findings in the urine analysis element of the study.

Analyte LGC Screen Capability MDT screening cut-offs VDT (ng/ml) (ng/ml) 6-MAM 1 2 1 n/a 5 1000 1 5 250 50 2 n/a 2 n/a 2 n/a 10 n/a (BZE) 10 300 5 300 10 200 10 300 5 n/a Gabapentin 100 n/a >1000 n/a 2 n/a MDMA 5 1000 1 300 5 n/a Morphine 5 300 1 n/a 5 n/a 5 n/a 25 n/a 100 n/a

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Analyte LGC Screen Capability MDT screening cut-offs VDT (ng/ml) (ng/ml) 5 n/a 10 n/a 5 n/a Stanozolol-3'OH 2 n/a 5 n/a 2 n/a Trenbolone 5 n/a 1 n/a 10 n/a

Initially the level of detection for cannabis was set much higher than for MDT, at 250 ng/ml. This was later adjusted to 25 ng/ml to provide a close comparison with MDT.

The screening levels reported in the above table are based on a post study determination of the method capability. The drugs representing the top 35 findings were spiked into blank urine samples and analysed using the methodology employed for the study. The instrument response was recorded for each drug and this value was used to calculate the drug concentration that would give a predefined instrument response. For most drugs, the instrument cut off that was used was 500000. The exception to this was cannabis (as carboxy THC) which initially had a cut-off of 100000 (equivalent to a drug concentration of 250ng/ml) and then latterly 10,000 (25ng/ml) due to very good signal to noise for that compound and a requirement to match the MDT sensitivity.

The screening levels by LCMS reflect the capability of the method rather than any predetermined cut off levels related to drug levels following therapeutic use.

SCRA Screen

The capability of the screen for synthetic was in the region of 50-100pg/ml. This method capability was much lower than that for the general screen primarily due to the instrumentation being used. A greater sensitivity is required for the detection of SCRAs due to the low levels seen in urine (and blood) samples.

Impact of enhanced sensitivity on interpretation of data

The ability to detect lower levels of drug gives a longer detection window following the administration of a drug. In controlled situations it would be possible to say from the level of drug and/or metabolite detected how long prior to sampling that the drug was taken. The speed with which a drug is eliminated from the body is termed the half life. Crudely speaking this is the time taken, normally measured in blood, for the concentration of a drug to reduce by one half. Using this information it is possible to determine from it’s concentration in a sample taken at particular time, when a particular drug was taken. This is wholly dependent however on knowing the dose of the drug and it’s half life. Using this data it is possible to determine a waiting time (the elapsed time after which it can be certain the drug would not be detected unless used subsequently). The waiting time is determined by the sensitivity of detection. The greater the sensitivity of detection the longer the waiting time.

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There is an extensive library of metabolic data for prescribed drugs and traditional drugs of abuse. Comparatively little data are available for SCRAs/NPS due to the ethical difficulties in conducting necessary clinical trials and the very wide and changing range of substances potentially available. Although some data may be available from cases of overdose, there are very few data on which to determine waiting times for these classes of drugs.

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Further Reading

The use of high resolution accurate mass spectrometry for rapid throughput, multi-drug screening. Hudson, Simon; Maynard, Steve; Timbers, Sarah. Proceedings of the 18th International Conference of Racing Analysts and Veterinarians, Jan 2010. p. 135-143

First European case of convulsions related to analytically confirmed use of the synthetic AM-2201. McQuade, David; Hudson, Simon; Dargan, Paul I.; Wood, David M. European Journal of Clinical vol. 69 issue 3 March 2013. p. 373 – 376

Delayed -like activity following analytically confirmed use of previously unreported synthetic cannabinoid analogues. L Schep, R Slaughter, S Hudson, R Place, M Watts Human & experimental toxicology. 09/2014

The Emergence and Analysis of S.Hudson and J. Ramsey. Drug Testing and Analysis, accepted for publication Feb 2011

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Analysis of by LGC Forensics

Seized items for analysis submitted were received at the laboratory and logged into the laboratory information management system (LIMS). The items were opened and examined a secure area, taking anti-contamination precautions and following standard operating procedures.

Samples are prepared for testing depending on whether they are in herbal, powder or form.

Medicinal preparations which are submitted as powders may well have originally been tablets but it will depend on how finely the tablets have been ground. A coarsely ground tablet will still have obvious tablet fragments or pieces of coating present but this is not always the case. A number of readily available over-the-counter and prescription tablets are white with no discernible coating and as such can be easily ground to a fine white powder. LGC examines thousands of white powders a year and these can be anything from extremely fine free-flowing powders through to heavily compressed blocks and sticky pastes. If it had been requested for samples to have been noted as being crushed tablets or other, the appearance would have been recorded by the analyst.

Herbals

Initially the analyst will make an informed judgement as to whether the herbal material has the appearance of cannabis or the herb typically used with SCRA compounds which is usually marshmallow leaf. The analysis of cannabis will be described below. Herbal material is difficult to homogenise easily so a sample will be well mixed and a representative portion will be taken for extraction. The herbal material will be soaked in for a few minutes to extract any SCRAs present. This ethanolic solution can then be injected directly into GCMS instrumentation for analysis.

Powders

Powder samples will be weighed initially and then homogenised by grinding in a pestle and mortar or similar. A series of colour tests will then be used on the powder to indicate which drug type may be present. These colour test results can aid which tests the scientist believes are most suitable to confirm the identity of the drugs present. If FTIR is to be used a small representative portion of the homogenised sample is placed on the instrument which has already been confirmed as being clean by appropriate background spectral monitoring. Pressure is applied to the sample using the ATR accessory and a spectrum is run. On completion of the scan the sample can be recovered if necessary as FTIR is a non-destructive technique. The spectrum obtained will then be compared to a database of known reference materials for identification. For GCMS testing a small portion of the homogenised sample is dissolved in an appropriate solvent and if necessary a derivitising reagent will also be added. The sample will be checked to ensure it has dissolved and placed on the GCMS instrument along with a solvent blank containing the same solvent used for dissolving the sample.

Tablets

Tablets will be weighed and initially checked against the TICTAC tablet identification database. If present on the database an identification test will be carried out to confirm the contents match the database. This test will be by either FTIR or GCMS analysis dependent on the drug present. Depending on the number of tablets present will determine whether a portion of a tablet is broken

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Typically, the initial stage of the examination involves performing a presumptive colour spot test, which gave an indication of the type of drug that may be present (for example turns purple in the presence of , orange in the presence of amphetamine and blue/black in the presence of ecstasy-type drugs).

Cannabis

Cannabis products are examined by a three stage process:

Initially the gross morphology of the sample will be visually examined and determined if it is consistent with cannabis products. Cannabis and marshmallow leaf, used with most SCRAs, are easily distinguishable visually. The cannabis product will then be examined microscopically and a number of characteristic features must be observed for the sample to be passed as likely to be cannabis. The third stage can then either be a colour test or a thin layer chromatography (TLC) technique. The colour test involves the use of the three step Negm’s or Duquenois-Levine test which produces a characteristic purple colouration at the final stage. Alternatively a TLC technique can be used whereby a small representative portion of the sample is extracted into a suitable solvent and an aliquot of this is placed on a suitable TLC plate. After placing in a suitable developing solvent and subsequent drying, the plate is sprayed with a fixing dye and the colours noted. The location and colour of the spots observed are compared to a reference cannabinoid mixture and reported accordingly.

Overview of methodology

The physical nature of the sample and the results from the initial colour test will determine how a sample is tested next. Samples believed to be one or two component mixtures are best suited to FTIR analysis, as although it is a powerful technique, it struggles with complex mixtures. Additionally the FTIR will not pick up SCRAs which have been soaked into herbal material. Powders, some tablets and some liquids are more suitable for FTIR analysis. The GCMS is better suited to analysing mixtures of substances and extracts from samples. The GC part of the technique is ideal for separating the components in a mixture which can then be identified by the MS detector. Which of the techniques used is determined by the analyst’s judgement call based on their experience and the samples they are examining.

GC-MS employs a combination of two techniques, involving separation of constituents in a mixture and a subsequent breakup of the constituents to produce a unique fragmentation pattern, which can then be compared to known standards. Samples analysed by GCMS were prepared by solvation of the sample into ethanol. Typically, one of two instrument methods was used to analyse samples depending on sample type. Most samples were screened for drugs using an 11.5 minute runtime method, however suspected synthetic cannabinoids were analysed using a 20 minute runtime method given the chemical nature of these drugs. GCMS analysis provides two characteristic sets of data. Specific drugs are detected at specific points during a runtime, which is characteristic for that drug. This so-called ‘retention time’ is compared to known reference standards, which are ran on the instrument monthly. Mass spectra obtained for each drug is further characteristic and they are compared to libraries of known reference standards, including those compiled in-house and commercially available ones.

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FTIR produces a unique chemical fingerprint of the sample, which can also be compared to known standards. The FTIR was equipped with an ATR accessory, which allows for quick analysis without the need for sample preparation. Spectra obtained by FTIR were compared to libraries of known reference standards, including those compiled in-house and commercially available ones.

The presence of a particular drug was confirmed by analysis using GC-MS and/or FTIR. The percentage purity of powdered drugs was not determined.

Results

The results from both tests were entered onto the LIMS. Results were subsequently peer reviewed by a further scientist before the final results were added to the results spreadsheet.

Samples that were not identified were sent to LGC Fordham to perform additional work on. Results were reported back to LGC forensics for inclusion in the main data set.

‘Spice’ herbs

LGC drugs team members are primarily degree educated chemists and, apart from identifying cannabis, have little or no botanical training. The carrier herb for most SCRAs is marshmallow leaf however this is known through bulk bags of the herbal material being labelled as such and some labelling from ‘head-shop’ packaging which have been submitted to our laboratories. LGC has never been formally requested to identify the marshmallow leaf and even if such a request was forthcoming we would contact Kew Gardens for their help.

Skunk cannabis

‘Skunk’ cannabis is a colloquialism that has become part of the legal system in England and Wales. The term originally referred to a particular cannabis plant variety which had been modified for growing indoors with a high THC concentration. The characteristic pungent aroma of the plant also contributed to its name. However, nowadays it refers to the unseeded flowering tops of the female cannabis plant. Cannabis plants can be either male or female and are quite distinctive from one another. At an early stage of growth their individual characteristics start to appear and the male plants are removed and destroyed. This encourages the unfertilised female plants to produce large flowering tops which tend to have higher levels of THC. Traditionally these flowering tops were referred to as ‘sinsemilla’ meaning ‘without seeds’ but the term ‘Skunk’ has superseded this. As ‘Skunk’ cannabis has a higher THC content it can command a higher price and therefore law enforcement agencies’ drugs valuation officers prefer to know if its ‘Skunk’ or traditional imported cannabis which tends to be a mix of leaf, flowers, seeds and stalk material.

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General Screen Database

The following table lists the drugs/chemicals that could be detected using the LC/MS methodology. The list includes those compounds specifically requested by NOMS. Many of the named drugs will be immediately recognisable. Many of the trivial drugs do not have common (or trivial) names and can only be named using standard .

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25iP-NBOMe 4-chloroamphetamine 25N-NBOMe 4-chloro-N,N-

2-aminoindane dimethylcathinone (Iso)butyryl-F- N- 4-cyano-1-methyl-4-phenyl benzyl analogue 2-aminoindane_80637201 1 4 fluorophenyl -B 4-EA-NBOMe 1-(3-chlorophenyl)-4-(3- 2C-C 4-ethylethcathinone chloropropyl)piperazine 2C-D 4-ethylmethcathinone 1-(3- 2C-E 4F PVP dihydroxy chlorophenyl)piperazine 2C-G 4F alpha PVP hydroxy 1,2-chlorophenylpiperazine 2C-H 4F alpha PVP reduced 1,3-dimethylbutylamine 2C-I 1,4 methoxy phenyl 4F alpha PVP reduced- 2C-N piperazine hydroxy 2C-P 1,4 trifluoromethylphenyl 4F-alpha PVP piperazine 2C-T-2 4F-alpha-POP 1,4-chlorophenylpiperazine 2C-T-4 4-fluoroamphetamine 1,4- 2C-T-7 4-fluorocathinone 11 hydroxy THC 2C-TFM 4-fluoroephedrine 1-benzyl-4-methyl- 2-Hydroxyethylflurazepam 4-fluoromethcathinone piperazine 2-Methoxy 4- 1-benzyl-4-phenyl-4- 2-methoxyphenylpiperazine fluoromethylamphetamine propionoxy-piperamide 2-methyl-AI 4-fluoronorephedrine 1-methylpyrrolidin-2-one 3,4 dimethyl 4-fluoropentedrone 1P LSD 3,4 MDPA 4-fluoro-PEP 1-phenyl-2-(1- 3,4 methylenedioxy-N- 4-fluorotropacocaine pyrrolidinyl)heptan-1-one benzylcathinone(BMDP) 4F-PBP 1P-LSD hydroxy 3,4,5 trimethoxy 4-HO-DPT 2,4- amphetamine 4-methoxy PV8 3,4- 2,5 dimethoxy-4- Dichloromethylphenidate 4-methoxy-alpha-PVP bromoamphetamine 3,4-dimethoxy-alpha-PHP 4-methoxy-alpha- pyrrolidinobutiophenone 2,5-dimethoxy-4- 3,4-dimethoxy-alpha-PVP iodophenethylamine(2-CI) 4-methoxy-PCP-dihydroxy 3,4-DMA-NBOMe 2,5-dimethoxy-4- 4-methoxy-PCP-hydroxy-1 iodophenethylamine-(2-CI) 3,4-Methylenedioxy-N,N- 4-methoxy-PCP-hydroxy-2 25B-NBOMe 3C-E 4-methoxyphenylpiperazine 25C-NBOMe 3C-P 4-methyl 25D-NBOMe 3-fluoro- 4'-Methyl-?- 25E-NBOMe pyrrolidinopropiophenone( 3-methoxy-4,5- 25G-NBOMe MPPP) methylenedioxyamphetami 25H-NBOMe ne 4-methyl-amphetamine 25I-NBMD 3-methoxyphenylpiperazine 4-methyl- 4 methoxy 4-methylethcathinone 25I-NBOMe 4Br-alpha-PVP 4-methyl- 25I-NBOMe desmethyl 4-bromoethcathinone 4-methylmethcathinone 25I-NBOMe hydroxy 4-chloro alpha PVP 4-methyl-

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4-methyl-N,N- 7-aminonitrazepam dihydro diethylcathinone AB-FUBINACA hydroxy 4-methyl-N,N- Benzedrone dihydroxy dimethylcathinone Benzedrone hydroxy 4-methyl-thioamphetamine Acetylmorphine 4-MMA-NBOMe Benzoylecgonine 4-OH MET AH-7921 4-OH MiPT 4-OH-DIPT 5' bromo alpha PVT alpha betameprodine 5,6-Methylenedioxy-2- ethylaminopentiophenone aminoindane-(MDAI) alpha ethyltryptamine B-ethyl 5/6-APDB alpha PHP 5-APB Alpha PVP bk-MDDMA 5-BPDi alpha PVT bk-PBDB 5-EAPB alphacetyl-methadol BMDB 5-EMAPB alphameprodine BMDB- hydroxy 5-iodo aminoindane BMDB-dihydro-desmethyl 5-IT-(5-(2- alpha-methyltryptamine BMDB-hydroxy desmethyl Aminopropyl)) 5-MAPB alpha-PBP brephedrone 5-MeO-DALT-dehydro- alpha-PBT hydroxy alpha-PNP 5-MeO-DALT-desallyl 5-MeO-DALT-desallyl AM-2201 Bromo MDMA hydroxy Indazolecarboxamide Bromophenethylamine 5-MeO-DALT-desmethyl analogue 5-MeO-DALT-dihydro- BTS-54-505 ( dihydroxy Amitriptylline metab) 5-MeO-DALT-dihydroxy Amphetamine Bufotenine 5-MeO-DALT-hydroxy Amphetamine OH buphedrone 5-MeO-DALT-hydroxy Amphetamine OH -NH3 buprenorphine desmethyl 1 Amphetamine-hydroxy- buprenorphine-nor 5-MeO-DALT-hydroxy methoxy desmethyl 2 Amphetamine-hydroxy- butyrylfentanyl 5-MeO-DALT-hydroxy methoxy loss NH3 C30-NBOMe didesmethyl ATM4 - SCH only Camphetamine 5-MeO-DALT- hydroxy_74693190 Carbamazepine B keto-2C-B 5-MeO-EIPT Carbamazepine-10,11- 5-MeO-MET dihydrodiol BB-22 5-methoxy dimethyl Carbamazepine-10,11- BDPA (IM) epoxide 5-methoxy-N- BDPA Rt Marker Carboxy THC isopropyltryptamine Benzedrone 6-allyl-6-nor-LSD Benzedrone carboxy 7 aminoclonazepam Benzedrone dihydro cathine-H2O

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Cathinone diazepam Diazepam - Hydroxy ethacetin ethcathinone Chlorpromazine Chlorpromazine di hydroxy ethylamphetamine Chlorpromazine hydroxy diethylpropion Chlorpromazine-hydroxy-N- Dihydrocodeine desmethyl DIHYDROCODEINONE Chlorpromazine-sulphoxide citalopram citalopram N desmethyl clephedrone dimenoxadole - N-desethyl clephedrone desmethyl Dimethamphetamine clephedrone reduced Dimethoxy- fentanyl Clonazepam chloroamphetamine Dimethoxy- iodoamphetamine dimethoxymethamphetami ne Dimethxoy- FLUNITRAZEPAM bromoamphetamine Flunitrazepam-7-amino Clozapine dimethylmorphine flunitrazepam-desmethyl Clozapine D4 Dimethyltryptamine Clozapine-desmethyl dipentylone Fluorophenethylamine Clozapine-hydroxy Fluorophenylpiperazine cocaine diphenyl pentan-1- Fluoxetine Cocaine - Hydroxy diphenylmethylpyrrolidine Fluoxetine - desmethyl Cocaine - Hydroxy methoxy Cocaine-N-ethyl DMCM Flurazepam N-Desethyl codeine DOIP D2PM () gabapentin d3 morphine (IM) Doxepin-hydroxy Gabapentin D10 DB-MDBP Doxepin-N-desmethyl-OH gamma-butyrolactone Demoxapam Ecgonine methyl ester glaucine-O-desmethyl EDDP D3 gramine EDDP methadone Desethyl metabolite D2PM - H2O HMMA Desoxy D2PM-hydroxy ergonovine Desoxyephedrine escalin Hydrocodone nor Hydroxy desmethyl diamorphine

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Morphine N-methyl- Phenylisobutylamine MPHP diphenylmethylpyrrolidine MPPP(4'-Methyl-?- N-methyl-N-ethyl- Phenylpropanolamine-H2O tryptamine pyrrolidinopropiophenone) Noopept MT-45 pipradol N-(4-hydroxyphenyl)- Pregabalin propanamide N,alpha diethyl norephedrine - N - ethyl premethadone norephedrine - N,N- diethyl N,N-diallyl-5- methoxytryptamine Norpseudoephedrine N,N- -H2O metabolite 1 N,N-dimethyl noscapine metabolite 2 phenethylamine PV8 PV-8 dihydroxy olanzapine naphyrone-dihydroxy PV-8 hydroxy naphyrone-dihydroxy- PV-8 reduced reduced PV-9 naphyrone-hydroxy naphyrone-hydroxy- reduced Quetiapine N-benzyl-1-phenethylamine paracetamol Quetiapine - desalkyl N-benzyl-4-methyl Paramethoxy-N- sulphoxide? buphedrone ethylamphetamine Quetiapine-dehydro- nefopam para-methyl-4- hydroxy Nefopam-N-desmethyl methylaminorex Quetiapine-desalkyl- n-ethyl hydroxy N-ethyl-1,2- Paroxol Quetiapine- diphenylethylamine PCP-3 methoxy deshydroxyethyl- N-ethyl-2C-B sulphoxide? N-ethyl-4- Quetiapine-nor methylnorpentedrone n-ethyl-buphedrone Pethidine - RH-34 N-hydroxy MDA hydroxydesmethyl N-hydroxy-N-methyl MDA Pethidine - dihydroxy SDB-001 N-hydroxy-N-methyl-3,4- ethylenedioxyamphetamine Selegiline - desmethyl (EFLEA) Sertraline Phenibut N-iso-propyl-1,2- Sertraline - hydroxy diphenylethylamine phenibut-O-methyl sertraline-desmethyl nitracaine sertraline-hydroxy- Nitrazepam desmethyl N-methyl 2C-B phentermine Sibutramine sildenafil N-methyl-BMDP Phentermine hydroxy

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Sildenafil desmethyl OH azine-hydroxy Sildenafil OH sildenafil thione U-47700 ST-91 URB-597 Stanozolol URB-597 breakdown

Stanozolol - 15 Hydroxy URB-754 Stanozolol - 16 alpha URB-754- hydroxy

Stanozolol - 3' hydroxy Venlafaxine Stanozolol- dihydroxy 1 W-15 Stanozolol- dihydroxy 2 W-18 Stanozolol- dihydroxy 3 X-tren Temazepam - Hydroxy Zaleplon-desethyl tenamfetamine (MDA) Zaleplon-hydroxy-1 tenamfetamine (MDA)-NH3 Zaleplon-hydroxy-2 tetramisole Zaleplon-hydroxy-3 Zolazepam thiopental Zolazepam N-oxide TH-PVP Zolazepam_119295621 zolazepam-desmethyl Tiletamine Zolazepam-desmethyl Tiletamine_927945368 Zolazepam-hydroxy-1 Tiletamine-dehydro Tiletamine-desethyl Zolpidem Tiletamine-desmethyl Zolpidem-COOH Tiletamine-hydroxy-1 Zolpidem-hydroxy-1 Tiletamine-hydroxy-2 Zolpidem-hydroxy-2 Tiletamine-hydroxy-3 Zolpidem-hydroxy-3 Tiletamine-hydroxy-5 Zolpidem-hydroxy-4 Tiletamine-OH Zopiclone Tramadol zopiclone N-oxide Tramadol - desmethyl Zopiclone-desmethyl Tramadol - didesmethyl Zopiclone-hydroxy Tramadol - hydroxy tramadol-N-desmethyl Trazodone Trazodone hydroxy trenbolone tribenzylpiperazine trifluoromethylphenylpiper

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SCRA Screen Database carboxylic acid ACPA-hydroxy 5F-AMB-desmethyl Adamantine variant-

5F-AMB-hydroxy hydroxy (4-methoxyphenyl)(1- ADB CHMINACA hydroxy 1 pentyl-1H-indol-3-yl) 5F-AMBICA hydroxy 1 methanone-hydroxy 5F-AMBICA hydroxy 2 ADB CHMINACA-hydroxy 2 0-1125-hydroxy 5-fluoropentyl-3- ADB-FUBINACA-hydroxy 1 2-isopropyl-5-methyl-1-(2,6- pyridinoylindole-hydroxy ADB-FUBINACA-hydroxy 2 dihydroxy-4- 5F-MN18-hydroxy ADBICA-5F-hydroxy 1 nonylphenyl)cyclohex-1- 5F-NPB-22 hydroxy 1 ADBICA-5F-hydroxy 2 ene-hydroxy 5F-NPB-22 hydroxy 2 ADBICA-hydroxy 1 4-HTMPIPO-hydroxy 5F-PY-PICA desfluoro- ADBICA-hydroxy 2 5Cl AKB-48 - adamantyl hydroxy ADB-PINACA-hydroxy 1 hydroxy 5F-PY-PICA-hydroxy 1 ADB-PINACA-hydroxy 2 5Cl AKB-48 - hydroxy 5F-PY-PICA-hydroxy 2 5F AB-PINACA deamino A-41988-hydroxy carboxylic acid Ajulemic acid-hydroxy A-796,260-hydroxy 5F AB-PINACA deamino AKB-48 F desfluoro carboxylic acid-hydroxy A834-735-hydroxy 1 hydroxypentyl 5F AB-PINACA-desfluoro A834-735-hydroxy 2 AKB-48 F-adamantyl hydroxy pentyl A-836,339-hydroxy hydroxy 5F ADB-PINACA-desfluoro- AB-001-hydroxy 1 AKB-48-adamantyl hydroxy hydroxy AB-001-hydroxy 2 AKB-48-F indole/alkyl hydroxy 5F ADB-PINACA-hydroxy-1 AB-002-hydroxy 1 AKB-48-F-adamantyl- 5F ADB-PINACA-hydroxy-2 AB-002-hydroxy 2 dihydroxy 5F -AMB desmethyl AB-005-azepine-hydroxy desfluoro hydroxy AKB-48-hydroxy AB-005-hydroxy 5F -AMB desmethyl hydroxy AM-087-hydroxy AB-CHMFUPPYCA 1 AM-1220 azepine-hydroxy 5F -AMB desmethyl hydroxy AB-CHMFUPPYCA-desamino AM1220-hydroxy 2 AB-CHMFUPPYCA-hydroxy AM1220-hydroxy *1* 5F EMB-PINACA-desethyl AB-CHMINACA deamino AM-1221-hydroxy 1 carboxylic acid 5F EMB-PINACA-desfluoro AM-1221-hydroxy 2 hydroxy AB-CHMINACA-dihydroxy AM-1235-hydroxy 1 5F EMB-PINACA-hydroxy 1 AB-CHMINACA-hydroxy 1 AM-1235-hydroxy 2 5F EMB-PINACA-hydroxy 2 AB-CHMINACA-hydroxy 2 AM-1241-hydroxy 1 5F PB-22 indazole hydroxy 1 AB-FUBINACA deamino AM1248-hydroxy 1 5F PY-PINACA desfluoro carboxylic acid AM1248-hydroxy 2 hydroxy AB-FUBINACA-fluorophenyl 5F PY-PINACA hydroxy 2 hydroxy AM2201 (4- fluoronaphthoyl)-hydroxy 1 5F PY-PINACA-hydroxy 1 AB-FUBINACA-hydroxy 1 AM2201 (4- 5F-AB-144-hydroxy AB-FUBINACA-indazole hydroxy fluoronaphthoyl)-hydroxy 2 5F-AB-FUPPYCA-desamino- AB-PINACA-hydroxy 1 AM-2201 (4 methoxy)- carboxylic acid hydroxy 1 AB-PINACA-hydroxy 2 5F-AB-FUPPYCA-hydroxy 1 AM-2201 (4 methoxy)- ACEA-hydroxy 5F-AB-PINACA hydroxy 1 hydroxy 2 5F-AB-PINACA hydroxy 2 acmd Compound#7-hydroxy AM2201 (chloronaphthoyl)- 5F-ADB-PINACA-desamino- ACMD Compound#8- hydroxy 1 hydroxy

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AM2201 (chloronaphthoyl)- pently hydroxy CUMYL-PICA hydroxy 1 hydroxy 2 AMB-PICA-5F-hydroxy CUMYL-PICA hydroxy 2 AM2201 chloronaphthoyl AMG-1-hydroxy CUMYL-PINACA-hydroxy 1 hydroxy pentyl metabolite AMG-36-hydroxy CUMYL-PINACA-hydroxy 2 AM2201 desfluoro hydroxy AMG-3-hydroxy CUMYL-THPINACA hydroxy pentyl AM-2201 AMG-41-hydroxy D3 Carboxy THC Indazolecarboxamide APP-CHMINACA-hydroxy-1 d5 hydroxypentyl JWH-018 analogue-hydroxy 1 APP-CHMINACA-hydroxy-2 dexamethasone AM-2201 BAY 38-7271-hydroxy DMHP-hydroxy Indazolecarboxamide BAY 59-3074-hydroxy EAM2201 - ethenyl-hydroxy analogue-hydroxy 2 BB-22 EAM2201-desfluoro AM2201 indole hydroxy BB-22-hydroxy 1 hydroxy pentyl AM2201-naphthoyl hydroxy BB-22-hydroxy 2 EAM2201-hydroxy AM-2202-hydroxy 1 BB-22-hydroxy 3 EG-018 hydroxy 2 AM-2202-hydroxy 2 BZ-2201 hydroxy 1 EG-018-hydroxy AM2232-hydroxy 1 BZ-2201 hydroxy 2 EMB-FUBINACA-desethyl AM2232-hydroxy 2 Carboxy THC EMB-FUBINACA-hydroxy AM2233-hydroxy CB-13-hydroxy 1 FAM-2201 hydroxypentyl AM-251-hydroxy CB-13-hydroxy 2 FAM-2201-carboxylic acid AM-4030-hydroxy CB-25-hydroxy FAM-2201-hydroxy AM404-hydroxy CB-65-hydroxy FAM-2201-hydroxy, AM-411-hydroxy hydroxypentyl CBM-2201-hydroxy 1 AM6257-5 fluoropenty - FDU-PB-22-hydroxy CBM-2201-hydroxy 1 *1* hydroxy 1 flunisolide CP 50,556-1-hydroxy AM6257-5 fluoropenty - fluocinolone acetonide CP-47,497-hydroxy hydroxy 2 Fluocinonide AM630-hydroxy CP-55,940-hydroxy fluocortolone AM-6527-hydroxy CP55244-hydroxy fluprednisolone AM-679-hydroxy CP-56,667-hydroxy FUB-AKB48-hydroxy AM-694-defluoro CP-945,598-hydroxy Fubimina-hydroxy AM-694-defluoro-COOH CRA-13-hydroxy 1 FUB-JWH-018-hydroxy 1 AM-694-defluoro-hydroxy CRA-13-hydroxy 2 FUB-JWH-018-hydroxy 2 AM-694-hydroxy Cumyl 5 F Pinaca deslfluoro FUB-NPB-22 hydroxy 1 AM-855-hydroxy hydroxypentyl FUB-NPB-22 hydroxy 2 AM-905-hydroxy Cumyl 5F PINACA hydroxy 2 FUB-PB22-hydroxy 1 AM-906-hydroxy Cumyl 5F PINACA-cumyl hydroxy FUB-PB22-hydroxy 2 AM-919-hydroxy Cumyl 5F PINACA-hydroxy 1 GP-1a-hydroxy AM-938-hydroxy Cumyl-5F-P7AICA-desfluoro GP-2a-hydroxy AMB-CHMICA hydroxy pentyl GW-405,833-hydroxy AMB-CHMICA-desmethyl Cumyl-5F-P7AICA-hydroxy 1 GW-405833-hydroxy AMB-CHMICA-hydroxy Cumyl-5F-P7AICA-hydroxy 2 HU-210-hydroxy AMB-CHMINACA hydroxy CUMYL-5FPICA-hydroxy 1 Hu-211-hydroxy AMB-CHMINACA-desmethyl CUMYL-5FPICA-hydroxy 2 HU-331-hydroxy AMB-FUBINACA-hydroxy CUMYL-BICA-hydroxy 1 hydrocortisone AMB-PICA-5F desfluoro CUMYL-BICA-hydroxy 2

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JTE 7-31-hydroxy JWH-049-hydroxy 2 JWH-133-hydroxy JTE-907-hydroxy JWH-050-hydroxy JWH-145-hydroxy JWH-004-hydroxy 1 JWH-051-hydroxy JWH-146-hydroxy JWH-004-hydroxy 2 JWH-071-hydroxy JWH-147-hydroxy JWH-007-hydroxy 1 JWH-072-hydroxy 1 JWH-149-hydroxy JWH-007-hydroxy 2 JWH-072-hydroxy 2 JWH-150-hydroxy JWH-016-hydroxy 1 JWH-073 (methyl JWH-167-hydroxy JWH-016-hydroxy 2 naphthoyl)-hydroxy 1 JWH-171-hydroxy JWH-018 Adamantine JWH-073 (methyl JWH-175-hydroxy naphthoyl)-hydroxy 1 *1* variant (AB-001) hydroxy 1 JWH-176-hydroxy JWH-073-hydroxy 1 JWH-018 Adamantine JWH-180-hydroxy variant (AB-001) hydroxy 2 JWH-073-hydroxy 2 JWH-181-hydroxy JWH-018 bromopentyl JWH-079-hydroxy JWH-182-hydroxy hydroxy 1 JWH-080-hydroxy 1 JWH-184-hydroxy JWH-018 bromopentyl JWH-080-hydroxy 2 hydroxy 2 jwh-185-hydroxy JWH-081-cyclohexylmethyl- JWH-189-hydroxy JWH-018 carboxamide- hydroxy 1 hydroxy 1 JWH-081-cyclohexylmethyl- JWH-192-hydroxy JWH-018 carboxamide- hydroxy 2 JWH-193-hydroxy hydroxy 2 JWH-081-hydroxy JWH-198-hydroxy JWH-018 chloropentyl- JWH-082-hydroxy JWH-199-hydroxy hydroxy 1 JWH-200-hydroxy JWH-018 chloropentyl- JWH-094-hydroxy hydroxy 1 *1* JWH-096-hydroxy JWH-200-piperazine JWH-018 parent IM JWH-098-hydroxy variant-hydroxy JWH-201-hydroxy JWH-018-hydroxy 1 JWH-116-hydroxy JWH-203-hydroxy JWH-018-hydroxy 2 JWH-122 (4 pentenyl)- JWH-019-hydroxy 1 hydroxy 1 JWH-204-hydroxy JWH-019-hydroxy 2 JWH-122 (4 pentenyl)- JWH-210-hydroxy hydroxy 2 JWH-211-hydroxy JWH-020-hydroxy 1 JWH-122 (5 chloropentyl)- JWH-212-hydroxy JWH-020-hydroxy 2 hydroxy 1 JWH-213-hydroxy JWH-022 methoxy JWH-122 (5 chloropentyl)- JWH-234-hydroxy analogue-hydroxy 1 hydroxy 2 JWH-022 methoxy JWH-122 (5- fluoropentyl)- JWH-237-hydroxy analogue-hydroxy 2 hydroxy 1 JWH-240-hydroxy JWH-022-hydroxy 1 JWH-122 (5- fluoropentyl)- JWH-242-hydroxy JWH-022-hydroxy 2 hydroxy 2 JWH-246-hydroxy JWH-0251-hydroxy 1 JWH-122 ethyl analogue - JWH-249-hydroxy JWH-0251-hydroxy 2 hydroxy 1 JWH-250 methyl-hydroxy JWH-122 ethyl analogue - JWH-030-hydroxy 1 JWH-250-hydroxy hydroxy 2 JWH-030-hydroxy 2 JWH-251 hydroxy JWH-122-cyclohexylmethyl- JWH-047-hydroxy 1 hydroxy 1 JWH-252-hydroxy JWH-047-hydroxy 2 JWH-122-cyclohexylmethyl- JWH-253-hydroxy JWH-048-hydroxy 1 hydroxy 2 JWH-262-hydroxy JWH-048-hydroxy 2 JWH-122-hydroxy 1 JWH-292-hydroxy JWH-049-hydroxy 1 JWH-122-hydroxy 2 JWH-302-hydroxy

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JWH-305-hydroxy hydroxy hydroxypentyl JWH-306-hydroxy M-CHMIC-hydroxy PB-22 5F-hydroxy 1 JWH-307-hydroxy MDMB-CHMICA-desmethyl PB-22 5F-hydroxy 2 JWH-308-hydroxy MDMB-CHMICA-hydroxy 1 PB-22 indazole-hydroxy 1 JWH-309 hydroxy 1 MDMB-CHMICA-hydroxy 2 PB-22-hydroxy 1 JWH-309 hydroxy 2 MDMB-CHMZCA PB-22-hydroxy 2 JWH-311-hydroxy MDMB-CHMZCA-desmethyl -(Win48098)- JWH-312-hydroxy MDMB-CHMZCA-hydroxy hydroxy JWH-314-hydroxy MDMB-FUBICA-hydroxy prednisolone JWH-346-hydroxy MDMD-CHMINACA hydroxy prednisone JWH-359-hydroxy 1 PX-1 hydroxy 1 JWH-364-hydroxy MDMD-CHMINACA hydroxy PX-1 hydroxy 2 2 JWH-365-hydroxy PX-2 hydroxy 1 -hydroxy JWH-367-hydroxy PX-2 hydroxy 2 -hydroxy JWH-368-hydroxy RCS-4 n-butyl-hydroxy methylprednisolone JWH-369-hydroxy RCS-4 n-methyl-hydroxy MMB-018 - hydroxy 1 JWH-370-hydroxy RCS-4-hydroxy MMB-018 - hydroxy 2 JWH-371-hydroxy RCS-8-hydroxy MMB-2201-hydroxy 1 JWH-373-hydroxy salvinorin A MMB-2201-hydroxy 2 JWH-387-hydroxy salvinorin A-hydroxy MN-18 - hydroxy 1 JWH-392-hydroxy SDB-001-hydroxy 1 MN-18 - hydroxy 2 JWH-394-hydroxy SDB-001-hydroxy 2 MN-25-hydroxy 1 JWH-397-hydroxy SDB-005 hydroxy 1 MN-25-hydroxy 2 JWH-398-hydroxy SDB-005 hydroxy 2 MN-25-methyl hydroxy 1 JWH-400-hydroxy SDB-005-5F hydroxy 1 MN-25-methyl hydroxy 2 JWH-412-hydroxy SDB-005-5F hydroxy 2 -hydroxy JWH-413-hydroxy SDB-006 hydroxy -hydroxy JWH-424-hydroxy SDB-006-5F hydroxy NM-2201-desfluoro- L-759,633-hydroxy STS-135 desfluoro hydroxy hydroxy pentyl L-759,656-hydroxy NM-2201-hydroxy 1 STS-135- hydroxy -hydroxy NM-2201-hyydroxy 2 STS-135-adamantyl hydroxy MAB-CHMINACA-hydroxy 1 NSC-001-hydroxy THJ-018-hydroxy MAB-CHMINACA-hydroxy 2 O-1057-hydroxy THJ-2201 desfluoro- MA-CHMINACA hydroxy 1 O-1238-hydroxy hydroxypentyl MA-CHMINACA hydroxy 2 O-1812-hydroxy THJ-2201 dihydroxy MAM-2201 hydroxy O-2372-hydroxy THJ-2201-hydroxy 1 MAM2201 desfluoro O-2545-hydroxy THJ-2201-hydroxy 2 hydroxypentyl O-2694-hydroxy triamcinolone MAM2201 desfluorohydroxypentyl O-806-hydroxy triamcinolone acetonide hydroxy O-823-hydroxy Unknown - C26H27NO2- MAM2201 Org-27569-hydroxy hydroxy desfluorohydroxypentyl Org-27759-hydroxy UR-144 (-2H)-hydroxy naphthoyl hydroxy Org-29647-hydroxy UR-144 5F desfluoro hydroxy pentyl MAM-2201 napthoyl PB-22 5F-desfluoro

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UR-144 5F hydroxy UR-144 5F indole hydroxy ur-144 chloropentyl- hydroxy UR-144 heptyl-hydroxy UR-144-5Cl indole hydroxy UR-144-dihydroxy UR-144-hydroxy URB-597-hydroxy URB-602-hydroxy URB-754 - hydroxy WIN 55212-2-hydroxy

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