IDENTIFICATION OF SYNTHETIC CANNABINOIDS IN HERBAL INCENSE ... · Cannabinoids in Herbal Incense Blends by GC/MS Application Compendium Introduction By Fran Diamond, Chemistry Technical

Application Compendium

IDENTIFICATION OF SYNTHETIC CANNABINOIDS IN HERBAL INCENSE BLENDS BY GC/MS

2

Table of ContentsIntroduction ..........................................................................................................................3

Sample Preparation..............................................................................................................4

Gas Chromatograph and Mass Spectrometer Conditions ...................................................5

GC/MS Total Ion Chromatogram of the Synthetic Cannabinoids Evaluated .......................6

JWH-007 .............................................................................................................................7

JWH-015 .............................................................................................................................8

JWH-018 .............................................................................................................................9

JWH-018 1-methylhexyl homolog ....................................................................................10

JWH-018 6-methoxyindole analog ...................................................................................11

JWH-019 ...........................................................................................................................12

JWH-073 ...........................................................................................................................13

JWH-073 2-methylbutyl homolog .....................................................................................14

JWH-081 ...........................................................................................................................15

JWH-098 ...........................................................................................................................16

JWH-122 ...........................................................................................................................17

JWH-133 ...........................................................................................................................18

JWH-200 ...........................................................................................................................19

JWH-201 ...........................................................................................................................20

JWH-203 ...........................................................................................................................21

JWH-210 ...........................................................................................................................22

JWH-250 ...........................................................................................................................23

JWH-251 ...........................................................................................................................24

JWH-302 ...........................................................................................................................25

JWH-398 ...........................................................................................................................26

HU-210...............................................................................................................................27

HU-210-di-TMS derivative .................................................................................................28

HU-211...............................................................................................................................29

HU-211-di-TMS derivative .................................................................................................30

HU-308...............................................................................................................................31

HU-308-mono-TMS derivative ...........................................................................................32

HU-331...............................................................................................................................33

HU-331-tri-TMS derivative .................................................................................................34

CB-25 .................................................................................................................................35

CB-25-di-TMS derivative ...................................................................................................36

CB-52 .................................................................................................................................37

CB-52-di-TMS derivative ...................................................................................................38

CP47,497 (C7 analog) .......................................................................................................39

CP47,497 (C7 analog)-di-TMS derivative .........................................................................40

CP47,497 (C8 analog) .......................................................................................................41

CP47,497 (C8 analog)-di-TMS derivative .........................................................................42

CP55,940 ...........................................................................................................................43

CP55,940-tri-TMS derivative .............................................................................................44

AM-694 ..............................................................................................................................45

AM-2201 ...........................................................................................................................46

RCS-4 .................................................................................................................................47

RCS-8 .................................................................................................................................48

WIN55,212-2 .....................................................................................................................49

WIN55-212-3 ....................................................................................................................50

3

Identifi cation of Synthetic Cannabinoids in Herbal Incense Blends by GC/MSApplication Compendium

IntroductionBy Fran Diamond, Chemistry Technical Leader, NMS Labs

The recent phenomenon of synthetic cannabinoid usage has given law enforcement and

testing laboratories a series of challenges to overcome in order to provide testing of these new

materials. These emerging substances are being manufactured and distributed worldwide,

but few legitimate certifi ed synthetic laboratories have been able to keep up with numerous

analogous and homologous materials that are used. Analytical laboratories have had a diffi cult

time obtaining pure reference material to use for positive identifi cation. The sheer number

of different chemicals has also thwarted the attempts of law-enforcement to crack down on

the distribution and use. These are legal drugs. As soon as legislation is passed banning their

use, different drugs show up in the next wave. These chemicals have different function group

chemistry that dictates a sample extraction procedure that will capture the various chemical

functionalities. Some of these new compounds are extremely potent in terms of dosage so that

they may only be present at trace levels. This necessitates the ability to analyze the complex

chromatographic data in the presence of large amounts of co-extractant material. These

materials are also structurally similar in terms of chromatographic retention time and mass

spectral appearance. Data analysis needs to be able to identify the subtle differences in these

species and be able to detect these substances in complex mixtures.

Test development and validation was completed at the Criminalistics division of NMS labs.

For 40 years, NMS Labs has been setting the standard for excellence in forensic testing with

state-of-the-art tests that other labs don’t or can’t provide. A national reference laboratory,

NMS Labs is unsurpassed in its scope of tests, accuracy of results, client service, scientifi c

expertise, and innovation.

4

HomogenizationThese synthetic cannabinoid preparations are produced by preparing a solution of the pure

chemical in acetone. Next, this acetone solution is sprayed onto the botanical matrix. The

botanical material is then air-dried, and is soft and light. These properties make it diffi cult to

crush into a homogeneous material to allow for proper representative sampling. We tested

numerous methods such as crushing in a mortar and pestle, an herb grinder, and even

electrical grinders and mills. These procedures did not produce acceptable results. We fi nally

developed a method of grinding by applying approximately 500 mg of material between two

5 in. x 5in. sheets of sandpaper (grit#100) and rubbing the two sheets together until a fi nely

divided powder was obtained.

ExtractionThe chemicals in this class contain various functional groups that require we use a generalized

method of extraction. We have used two basic strategies: an acid/base combined extraction

and a simple methanol incubation followed by centrifugation. In the acid/base extraction, we

acidify an aliquot of sample (between 50 and 100 mg of ground material) by adding 1 mL of

de-ionized water followed by the addition of 3 drops of 10% HCl. We next add 1 mL of solvent

extraction (95% methylene chloride/5% isopropanol v/v) and mix briefl y. We centrifuge the

sample and remove the bottom solvent layer and keep. To the remaining aqueous mixture,

we add 2 drops of concentrated ammonium hydroxide solution and add 1 mL of the above

mentioned mixed solvent. Tubes are again mixed and centrifuged, and the lower solvent layer

is removed and combined with the initial solvent. This combined extract is then mixed briefl y

and transferred to an autosampler vial and capped. It is now ready for instrumental analysis.

DerivatizationSome of the chemicals used in production contain active, polar funtional groups such as

alcohols, phenols, amides and ketones that negatively impact the GC/MS analysis in their

native form. To enhance sensitivity and detectability, we will employ a derivatization procedure

to shield these polar groups.

We employ the use of BSTFA with 1% TMCS. The procedure is performed as follows: The

above mentioned extracts are evaporated to dryness at room temperature under a gentle

stream of nitrogen. It is crucial that these extracts are completely dry and free from residual

water or alcohol as this will neutralize the derivatizing agent. Next, 50 uL of SELECTRA-SIL®

(BSTFA with 1% TMCS) was added and the tube capped. Tube is incubated at 70 °C for thirty

minutes. Upon cooling, the derivatized mixture is transferred to an autosampler vial with a

200 µL insert, capped, and sealed. Samples are now ready for instrumental analysis.

Sample Preparation

5

Gas Chromatograph and Mass Spectrometer ConditionsGCAgilent technologies 6890 with fast oven, Autoinjector and tray

Inlet EPC Split/splitless

Mode Constant pressure

Injection type Splitless

Injection volume (uL) 1.0

Inlet temperature (°C) 265

Pressure nominal (psig) 20.70

Purge fl ow (ml/min.) 50

Purge time (min.) 0.30

Gas type Helium

OvenVoltage (VAC) 240

Initial Oven Temp. (°C) 50

Initial oven hold (min.) 0

Ramp rate (°C/min.) 20

Final Temp. (°C) 340

Final hold (min.) 2.0

Total Run Time (min.) 16.50

Equilibration time (min.) 0.1

ColumnType DB-1

Agilent part number 128-1012

Length (m) 12

Diameter (mm) 0.200

Film Thickness (um) 0.33

Nominal Initial Flow (mL/min) 2.6

MSDAgilent Technologies 5973 network

Vacuum pump Turbo

Tune File Atune.U

Mode scan

Solvent delay (min.) 1.5

EM voltage Atune Voltage

Low mass (amu) 40

High mass (amu) 620

Threshold 250

Sampling 1

Quad temp (°C) 150

Source temp (°C) 230

Transfer line temp (°C) 300

6

GC/MS Total Ion Chromatogram of the Synthetic Cannabinoids Evaluated

8.00 8.50 9.00 9.50 10.00 10.50 11.00 11.50 12.00 12.50 13.00 13.50 14.00 14.50 15.000

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Abundance

1

2

3

4

5

6

7

8

910

12

11

13

15

14

16

1718

19

20

21

22

23

24

2526

27

1) Internal standard 2) JWH-133 3) HU-331 4) CP47,497 (C7 analog) 5) CP47,497 (C8 analog) 6) HU-308 7) JWH-251 8) JWH-203 9) JWH-250 10) RCS-4 11) CP55,940 12) HU-210/211 13) JWH-015 14) AM-694 15) JWH-073 16) JWH-018 17) JWH-019 18) AM-2201 19) JWH-122 20) RCS-8 21) JWH-398 22) JWH-210 23) CB-25 24) JWH-081 25) CB-52 26) JWH-200 27) WIN55,212-2/-3

7

JWH-007

Chemical name 1-pentyl-2-methyl-3-(1-naphthoyl)indole

Molecular formula C25

H25

NO

Molecular mass 355.471

Major GC/MS ions 355.2, 354.2, 127.0, 340.1, 298.1

Ions used for analysis Target 355

Qualifi er-1 340

Qualifi er-2 127

Retention time 12.97 minutes

LOD Not yet established

Mass Spectrum:

Molecular Structure:

30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 3600

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A ecnadnub355

127

340

298155

270

43 228

284254 312241

11532677 215

101 142 1728955 163 184 19863 134 207191 277108

8

JWH-015

Chemical name (2-Methyl-1-propyl-1H-indol-3-yl)-1-naphthalenylmethanone

Molecular formula C23H21NO


Major GC/MS ions 327.3, 326.3, 310.3, 270.2, 200.2, 127.1

Ions used for analysis Target 327.3

Qualifi er-1 310.3

Qualifi er-2 270.2



Additional comments JWH-015 does not derivatize.

JWH-015 and JWH-073 are formula isomers. They have

similar fragmentation patterns with slight differences in

retention time.

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 3300

100000

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A ecnadnub 327

310

270

200127

155298

284254

24121311577 103 163142 226134 172148 18441 89 2782646351 190

9

JWH-018

Chemical name Naphthalen-1-yl-(1-pentylindol-3-yl)methanone



Major GC/MS ions 341.3, 324.3, 284.2, 270.2, 214.2, 127.1


Qualifi er-1 324.3

Qualifi er-2 284.2


LOD 0.02 mg/g

Additional comments JWH-018 will not derivatize

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 3500

50000

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A ecnadnub 341

284

214324

127

270144

155

254167 241

1164318610189 22677 31229855 20263 133 174

10

JWH-018 1-methylhexyl homolog

Chemical name (1-(Heptan-2-yl)-1H-indol-3-yl)(naphthalen-1-yl)methanone

(racemate)


H27

NO


Major GC/MS ions 298.1, 369.2, 127.0, 270.1, 299.1


Qualifi er-1 369

Qualifi er-2 127



Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 3800

50000

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A ecnadnub298

369

127

270

155144242

25441 57

354116 2141701018977 284226 340189 312 32620067 179

11

JWH-018 6-methoxyindole analog

Chemical name (6-methoxy-1-pentyl-1H-indol-3-yl)(naphthalen-1-yl)-

methanone


H25

NO2


Major GC/MS ions 371.1, 372.1, 244.1, 370.1, 314.0


Qualifi er-1 244

Qualifi er-2 314



Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 3800

50000

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A ecnadnub371

244 314354

155127

300

174 257147 28421643 228 270202 34032876171177 102 1898955 13563 181109 293

12

JWH-019

Chemical name Naphthalen-1-yl-(1-pentylindol-3-yl)methanone



Major GC/MS ions 355.3, 338.3, 284.2, 228.2, 127.1, 155.1


Qualifi er-1 284.2

Qualifi er-2 338.3


LOD 0.02 mg/g

Additional comments JWH-019 will not derivatize. JWH-019 is a formula isomer of

JWH-122 and has similar fragmentation pattern with only a

slight difference in retention time.

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 3600

50000

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A ecnadnub 355

284

338228

127

155 270144

254167 241

43 116 200 215 32610177 89 177 298 31255 18713563

13

JWH-073

Chemical name naphthalen-1-yl-(1-butylindol-3-yl)meth



Major GC/MS ions 327.3, 310.3, 284.2, 200.2, 127.1, 144.1


Qualifi er-1 310.3

Qualifi er-2 284.2


LOD 0.02 mg/g

Additional comments JWH-073 does not derivatize. JWH-073 is a structural isomer

of JWH-015 with similar fragmentation and a slight difference

in retention time.

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 3300

50000

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A ecnadnub 327

284200

310

127

144270

155254167 241

11621389 1017741 226 29857 18963 13551 176 278264

14

JWH-073 2-methylbutyl homolog

Chemical name N-(2-methylbutyl)-3-(1-naphthoyl)-indole


H23

NO


Major GC/MS ions 284.0, 341.1, 127.0, 214.0, 285.0


Qualifi er-1 341

Qualifi er-2 127



Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 3500

20000

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A ecnadnub284

341

127

214

155

270144

254 32443 167 241

11610277 89 22618655 63 312202 294176135 194

15

JWH-081

Chemical name 4-methoxynaphthalen- 1-yl- (1-pentylindol- 3-yl)methanone

Molecular formula C25H25NO2


Major GC/MS ions 371.3, 354.3, 314.3, 370.3, 214.2, 185.1


Qualifi er-1 354.3

Qualifi er-2 314.3


LOD 0.02 mg/g


Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 3800

50000

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A ecnadnub 371

354314

214

185

144197 300

285157114 241 270 34032822812743 25717110289 13677 46155 20763

16

JWH-098

Chemical name 4-methoxynaphthalen-1-yl-(1-pentyl-2-methylindol-3-yl)

methanone


H27

NO2


Major GC/MS ions 385.2, 370.2, 185.0, 384.2, 368.2


Qualifi er-1 370

Qualifi er-2 185



Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 3900

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A ecnadnub385

370

185

43328158 314300114

228142127

255 342171 241 270 356212202 285

1038855 7765

17

JWH-122

Chemical name 1-Pentyl-3-(4-methyl-1-naphthoyl)indole



Major GC/MS ions 355.3, 338.3, 298.2, 284.2, 214.2, 144.1


Qualifi er-1 338.3

Qualifi er-2 298.2


LOD not yet established

Additional comments JWH-122 will not derivatize. JWH-122 is a structural isomer

of JWH-019 with similar fragmentation and slight difference in

retention time.

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 3600

100000

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A ecnadnub 355

338298

214

284

144 169 181254 270115 241

43 226 326128 312102 53198 155 20255 77 18963 162

18

JWH-133

Chemical name (6aR,10aR)-3-(1,1-Dimethylbutyl)-6a,7,10,10a-tetrahydro

-6,6,9-trimethyl-6H-dibenzo[b,d]pyran

Molecular formula C22H32O


Major GC/MS ions 312.3, 269.2, 229.2, 270.2, 201.2, 159.1


Qualifi er-1 269.2

Qualifi er-2 229.2


LOD 0.02 mg/g


Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 3200

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A ecnadnub 269

312

229

2011591851918543 171119 13510791 297257127 147 24421316577 14155 113 15369 17899 237

19

JWH-200

Chemical name (1-(2-morpholin-4-ylethyl)indol-3-yl)-naphthalen-1-

ylmethanone

Molecular formula C25H24N2O2


Major GC/MS ions 100.0, 384.3, 127.1, 155.1, 56


Qualifi er-1 100.0

Qualifi er-2 127.1


LOD 0.05 mg/g


Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 3900

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A ecnadnub 100

384

12756 155

254 28470 24142 115 226213 270 339170143 29689 187 19978

20

JWH-201

Chemical name 2-(4-methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)-ethanone


H25

NO2


Major GC/MS ions 214.1, 144.0, 215.1, 121.0, 116.0


Qualifi er-1 144

Qualifi er-2 335



Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 3500

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A ecnadnub214

144

121

43 129 33578 89 10251 17015711463 204191184 27823471 221 603052177 31926216313795 268

21

JWH-203

Chemical name 2-(2-chlorophenyl)-1-(1-pentylindol-3-yl)ethanone

Molecular formula C21H22ClNO


Major GC/MS ions 214.2, 144.1, 339.3


Qualifi er-1 144.1

Qualifi er-2 339.3




Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 3400

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A ecnadnub 214

144

339116 1298943 102 304282204157 17063 184 2467755 232177

22

JWH-210

Chemical name 4-ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone



Major GC/MS ions 369.3, 352.3, 340.3, 312.3, 183.1, 195.1


Qualifi er-1 352.3

Qualifi er-2 312.3




Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 3800

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A ecnadnub 369

352

312

340

195183 214 298270 283

153139 326253115 128 24143 22616777

23

JWH-250

Chemical name 2-(2-methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone



Major GC/MS ions 214.2, 144.1, 335.3


Qualifi er-1 144.1

Qualifi er-2 335.3


LOD 0.02 mg/g


Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 3400

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A ecnadnub 214

144

335

11643 91 12910265 170 8727517855 204184 432191122 306246 913122771801

24

JWH-251

Chemical name 2-(2-methylphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone



Major GC/MS ions 214.2, 319.3, 144.1


Qualifi er-1 319.3

Qualifi er-2 144.1


LOD 0.02 mg/g


Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 3200

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A ecnadnub 214

144

31911643 1291058977 170157 26220418455 63 230 290220

25

JWH-302

Chemical name 2-(3-methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)-ethanone


H25

NO2


Major GC/MS ions 214.1, 144.0, 215.1, 116.0, 335


Qualifi er-1 144

Qualifi er-2 335



Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 3400

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A ecnadnub214

144

11643 3351299178 10265 17055 157 204 236192 278184 222 264177 319603942108 292032123 136 150

26

JWH-398

Chemical name 1-pentyl-3-(4-chloro-1-naphthoyl)indole

Molecular formula C24H22ClNO


Major GC/MS ions 375.3, 358.3, 318.3, 214.2, 189.1, 144.1


Qualifi er-1 358.3

Qualifi er-2 318.3


LOD 0.02 mg/g


Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 3800

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A ecnadnub 375

318214

358

144

189

161304

126254 269201 340241

2901164328310289 226175 332 34727675 15355 13563

27

HU-210Chemical name (6aR,10aR)- 9-(Hydroxymethyl)- 6,6-dimethyl-

3-(2-methyloctan-2-yl)- 6a,7,10,10a-tetrahydrobenzo [c]

chromen- 1-ol

Molecular formula C25H38O3


Major GC/MS ions 386.3, 302.3, 287.2, 316.3, 330.3, 344.3


Qualifi er-1 302.3

Qualifi er-2 287.2


LOD 0.02 mg/g

Additional comments Forms di-TMS derivative with BSTFA

Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 3900

100000

200000

300000

400000

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600000

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1300000

m/z-->

A ecnadnub 302

386

287

316330

344269241217201 24918743 164 227 35391 133 14969 17570155 119 36879 141 257209 277

28

HU-210 di-TMS derivative

Chemical name (6aR,10aR)- 9-(Hydroxymethyl)- 6,6-dimethyl-


chromen- 1-ol-di-TMS derivative

Molecular formula C31H54O3Si2


Major GC/MS ions 530.5, 446.4, 531.5, 359.3, 460.4, 474.4


Qualifi er-1 446.4

Qualifi er-2 359.3


LOD 0.004 mg/g

Additional comments HU-210 is indistinguishable from HU-211.

Mass Spectrum:


60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 5400

100000

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600000

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m/z-->

A ecnadnub 446

53073

359

460 474216

273 488431321259 515133 34123691 105 397289299147 373 387195 247119 179165 418

29

HU-211

Chemical name (6aS,10aS)-9-(Hydroxymethyl)- 6,6-dimethyl-


chromen-1-ol



Major GC/MS ions 386.3, 302.3, 287.2, 316.3, 330.3, 344.3


Qualifi er-1 302.3

Qualifi er-2 287.2


LOD 0.02 mg/g


HU-211 is indistinguishable from HU-210

Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 3900

50000

100000

150000

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m/z-->

A ecnadnub 302

386

287

316330

34426924121743 201 24918716491 227 35355 69 133119107 17514979 368

141 257209 277

30

HU-211-di-TMS derivative

Chemical name (6aS,10aS)-9-(Hydroxymethyl)- 6,6-dimethyl-


chromen-1-ol-di-TMS derivative



Major GC/MS ions 530.5, 446.4, 531.5, 359.3, 460.4, 474.4


Qualifi er-1 446.4

Qualifi er-2 359.3


LOD 0.004 mg/g

Additional comments HU-211 is indistinguishable from HU-210

Mass Spectrum:


40 60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 540 560 580 6000

50000

100000

150000

200000

250000

300000

350000

400000

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1000000

m/z-->

A ecnadnub 446

73

530

359

460 474216

488273259 431321237 341133 51557 147 289 39791 105 163 195 373119 179 418385309

31

HU-308

Chemical name [(1R,2R,5R)-2-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-

7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl] methanol



Major GC/MS ions 277.2, 318.3, 353.3, 414.4, 293.2, 383.3


Qualifi er-1 318.3

Qualifi er-2 353.3



Additional comments Forms mono-TMS derivative with BSTFA

Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 390 400 410 4200

50000

100000

150000

200000

250000

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m/z-->

A ecnadnub 318

353

277

414

293

383233

341215180 39671 11943 36591 165 191 205 25557 151105 285265 30513579 241 329

32

HU-308-mono-TMS derivative

Chemical name [(1R,2R,5R)-2-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-

7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl] methanol-mono-

TMS derivative

Molecular formula C30H50O3Si


Major GC/MS ions 277.2, 318.3, 353.3, 383.3, 396.3, 486.4


Qualifi er-1 396.3

Qualifi er-2 353.3



Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 390 400 410 420 430 440 450 460 470 480 490 5000

20000

40000

60000

80000

100000

120000

140000

160000

180000

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220000

240000

260000

280000

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340000

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m/z-->

A ecnadnub 35373

277

396318

383

157103486365

91 131119 41857 239179

209 443191 471291227 255141333265167 305 430

33

HU-331

Chemical name 3-hydroxy-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-

cyclohexen-1-yl]-5-pentyl-2,5-cyclohexadiene-1,4-dione



Major GC/MS ions 313.3, 311.3, 328.3, 247.2, 237.2, 204.2


Qualifi er-1 313.3

Qualifi er-2 247.2



Additional comments Forms tri-TMS derivative with BSTFA

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 3300

5000

10000

15000

20000

25000

30000

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40000

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m/z-->

A ecnadnub 313

247

237

204328

220

26091

191109 175 28716179 11941 27322967 211128 15255145135 296183103 169 198

34

HU-331-tri-TMS derivative

Chemical name 3-hydroxy-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-

cyclohexen-1-yl]-5-pentyl-2,5-cyclohexadiene-1,4-dione-tri-

TMS derivative



Major GC/MS ions 455.4, 384.3, 529.5, 544.4


Qualifi er-1 384.3

Qualifi er-2 544.5



Mass Spectrum:


40 60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 5400

10000

20000

30000

40000

50000

60000

70000

80000

90000

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110000

120000

130000

140000

150000

160000

170000

m/z-->

A ecnadnub 455

384

544529

370 411 477295 39654 519186 434100

35

CB-25

Chemical name N-cyclopropyl-11-(3-hydroxy-5-pentylphenoxy)-undecanamide



Major GC/MS ions 403.4, 124.1, 57.0, 181.1, 347.3, 374.3


Qualifi er-1 124.1

Qualifi er-2 57.0




Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 390 400 4100

50000

100000

150000

200000

250000

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m/z-->

A ecnadnub 403

124

57

181

224 347

374290

69 138 36014941 318

262 3048310799

163 202 332193 247 276 38591 233210115

36

CB-25-di-TMS derivative

Chemical name N-cyclopropyl-11-(3-hydroxy-5-pentylphenoxy)-undecanamide

di-TMS derivative

Molecular formula C31H57NO3Si2


Major GC/MS ions 547, 532, 504, 156, 184, 196


Qualifi er-1 532.5

Qualifi er-2 504.5



Mass Spectrum:


40 60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 540 560 5800

50000

100000

150000

200000

250000

300000

350000

400000

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800000

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900000

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m/z-->

A ecnadnub 73156

184

171196

547296

116 532504

55128

282 407 420240 325212 226 253 268144 491476 518100392 448364337

37

CB-52

Chemical name N-cyclopropyl-11-(2-hexyl-5-hydroxyphenoxy)-undecanamide



Major GC/MS ions 417.4, 123.1, 261.2, 346.3, 360.3, 194.1


Qualifi er-1 261.2

Qualifi er-2 346.3




Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 390 400 410 4200

50000

100000

150000

200000

250000

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600000

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m/z-->

A ecnadnub 123

417

261

346

360

194

58

149137 16369 289 33241 22481 95 107388177 374207 399233 318247 301275216115

38

CB-52-di-TMS derivative

Chemical name N-cyclopropyl-11-(2-hexyl-5-hydroxyphenoxy)-undecanamide

di-TMS derivative

Molecular formula C32H59NO3Si2


Major GC/MS ions 561.5, 546.5, 505.5, 296.2, 195.1, 156.1


Qualifi er-1 546.5

Qualifi er-2 505.5



Mass Spectrum:


40 60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 540 5600

50000

100000

150000

200000

250000

300000

350000

400000

450000

500000

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600000

650000

700000

750000

800000

850000

900000

950000

m/z-->

A ecnadnub 73

156

195

184

171

296561

54650555 116 128 227

490282240 448209 267254 518100 337144 532312 421 476434390

39

CP47,497 (C7 analog)

Chemical name 2-[(1R,3S)-3-hydroxycyclohexyl]- 5-(2-methyloctan-2-yl)

phenol



Major GC/MS ions 215.2, 233.2, 318.3, 300.3


Qualifi er-1 215.2

Qualifi er-2 233.2


LOD 0.01 mg/g


Compound shares some common ions with the C8 analog.

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 3200

50000

100000

150000

200000

250000

300000

350000

400000

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850000

900000

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1000000

1050000

1100000

m/z-->

A ecnadnub 215

233

318

300

81 161147 246107 173 18743 135

57 91 20112171 115 128 257 2851419765 27215551 181

40

CP47,497 (C7 analog)-di-TMS derivative

Chemical name 2-[(1R,3S)-3-hydroxycyclohexyl]- 5-(2-methyloctan-2-yl)

phenol-di-TMS derivative



Major GC/MS ions 377, 462, 378, 463


Qualifi er-1 462.4

Qualifi er-2 378.3


LOD 0.002 mg/g

Additional comments Compound shares some common ions with the C8 analog.

Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 390 400 410 420 430 440 450 460 4700

50000

100000

150000

200000

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500000

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600000

650000

m/z-->

A ecnadnub 377

73

462

28743

2335720514785 219129 305101 245179 419191 447116 259169 363273 349157 319 335 391 406

41

CP47,497 (C8 analog)

Chemical name 2-[(1R,3S)-3-hydroxycyclohexyl]- 5-(2-methylnonan-2-yl)

phenol



Major GC/MS ions 215.2, 233.2, 314.3, 332.3


Qualifi er-1 215.2

Qualifi er-2 233.2


LOD 0.02 mg/g


Compound shares some common ions with the C7 analog.

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 3400

50000

100000

150000

200000

250000

300000

350000

400000

450000

500000

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600000

650000

700000

750000

800000

850000

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950000

1000000

1050000

m/z-->

A ecnadnub 215

233

332

314

81 161147107 26018717313543 57 2011219171 128 299244 271 28615599

42

CP47,497 (C8 analog)-di-TMS derivative

Chemical name 2-[(1R,3S)-3-hydroxycyclohexyl]- 5-(2-methylnonan-2-yl)

phenol-di-TMS derivative



Major GC/MS ions 377.3, 476.4, 378.3, 477.4


Qualifi er-1 377.3

Qualifi er-2 378.3


LOD 0.004 mg/g

Additional comments Compound shares some common ions with the C7 analog.

Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 390 400 410 420 430 440 450 460 470 480 4900

50000

100000

150000

200000

250000

300000

350000

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650000

700000

750000

m/z-->

A ecnadnub 377

73

476

28743 57233

20514785 219129 542101 177 191 433303 461319259116 161 363273 393349333 404 420

43

CP55,940

Chemical name 2-[(1R,2R,5R)-5-hydroxy-2-(3-hydroxypropyl) cyclohexyl]-5-

(2-methyloctan-2-yl)phenol



Major GC/MS ions 273.2, 147.1, 376.3, 121.1, 304.3, 358.3


Qualifi er-1 273.2

Qualifi er-2 358.3


LOD 0.05 mg/g

Additional comments Forms tri-TMS derivative with BSTFA

Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 3800

10000

20000

30000

40000

50000

60000

70000

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120000

m/z-->

A ecnadnub 273

147

376

121

161 187304

213358135

23343

71 25555 10793 29179 173

199 246220312154 343114100 283 330

44

CP55,940-tri-TMS derivative

Chemical name 2-[(1R,2R,5R)-5-hydroxy-2-(3-hydroxypropyl) cyclohexyl]-5-

(2-methyloctan-2-yl)phenol-tri-TMS derivative



Major GC/MS ions 593.5, 419.4, 327.3, 305.3, 219.2, 121.1


Qualifi er-1 419.4

Qualifi er-2 327.3


LOD 0.01 mg/g

Mass Spectrum:


60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 540 560 580 6000

100000

200000

300000

400000

500000

600000

700000

800000

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m/z-->

A ecnadnub 73

593

327

305

219419

121147

233285

205

25993 245185 345133 577271 386361 465169105 50261 372 487434398

45

AM-694

Chemical name 1-[(5-fl uoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone

Molecular formula C20H19FINO


Major GC/MS ions 435.3, 232.1, 220.1, 360.2


Qualifi er-1 232.1

Qualifi er-2 220.1



Additional comments Does not form derivative

Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 390 400 410 420 430 4400

200000

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600000

800000

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m/z-->

A ecnadnub 435

232

220

360

204144308

164 190116 13076 176 25610241 33189 246 3186350 415288154

46

AM-2201

Chemical name 1-[(5-fl uoropentyl)-1H-indol-3-yl]-(naphthalen-1-yl)methanone

Molecular formula C24H22FNO


Major GC/MS ions 127.1, 232.2, 284.2, 359.3


Qualifi er-1 232.2

Qualifi er-2 284.2



Additional comments Does not form derivative

AM-2201 is the fl uoro-analog of JWH-018

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 3700

50000

100000

150000

200000

250000

300000

350000

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650000

700000

m/z-->

A ecnadnub 359

232

284 342

127

144 270

155 254167241116

41 21389 10277 330179 204 29822569 188 3225951 135 310

47

RCS-4

Chemical name ((4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone)



Major GC/MS ions 321.3, 264.2, 214.2, 135.1, 144.1, 186.1


Qualifi er-1 264.2

Qualifi er-2 214.2



Additional comments RCS-4 will not derivatize

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 3300

100000

200000

300000

400000

500000

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m/z-->

A ecnadnub 321

264

214135

144186

118 222 30677 92 29010743 129 152 250 278192178170 207 23663 101 16351

48

RCS-8

Chemical name 1-(1-(2-cyclohexylethyl)-1H-indol-3-yl)-2-(2-methoxyphenyl)

ethanone



Major GC/MS ions 254.2, 144.1, 375.3


Qualifi er-1 144.1

Qualifi er-2 375.3



Additional comments RCS-8 will not derivatize

Mass Spectrum:


40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 3800

200000

400000

600000

800000

1000000

1200000

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2200000

m/z-->

A ecnadnub 254

144

37555 69 12941 91 158116102 27817078 207 218178 234198 227

49

WIN55,212-2

Chemical name (R)-(+)-[2,3-Dihydro-5-methyl-

3-(4-morpholinylmethyl)pyrrolo

[1,2,3-de]-1,4-benzoxazin-6-yl]-

1-napthalenylmethanone



Major GC/MS ions 100.0, 127.1, 155.1, 326.3, 426.4, 56.0


Qualifi er-1 426.4

Qualifi er-2 127.1


LOD 0.12 mg/g

Additional comments WIN55,212-2 will not derivatize. WIN55,212-2 and

WIN55,212-3 are isomers and are indistinguishable.

Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 390 400 410 420 4300

100000

200000

300000

400000

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900000

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1100000

m/z-->

A ecnadnub 100

426

12756 155

3267042 254 298115 170 382202 241226 270 310142 21389 340184

50

WIN55,212-3

Chemical name [(3S)-2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl)

pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenyl-

methanone



Major GC/MS ions 100.0, 127.1, 155.1, 326.3, 426.4, 56.0


Qualifi er-1 426.4

Qualifi er-2 127.1


LOD 0.12 mg/g

Additional comments WIN55,212-2 will not derivatize. WIN55,212-2 and

WIN55,212-3 are isomers and are indistinguishable.

Mass Spectrum:


30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 390 400 410 420 4300

100000

200000

300000

400000

500000

600000

700000

800000

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1500000

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2200000

m/z-->

A ecnadnub 100

426

12715556

3267042 170 254 298281241722511 270202142 310189 213 338 35589

For more information

Learn more:

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This information is subject to change without notice.

© Agilent Technologies, Inc. 2012, 2016Printed in the USA March 24, 20165990-7967EN

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