October 2010NOTE: prices and availability subject to change without notice

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Synthetic Cannabinoid Screening

BackgroundIn 2008, a German pharmaceutical company by the name of THC Pharm confirmed the presence of a synthetic cannabinoid (CB) in a commercial herbal incense product called ‘Spice’.1 It was believed at the time that commercial incense products were being sprayed with these synthetic CBs and used as designer marijuana substitutes. Shortly after this report, seven more incense blends were tested by researchers at the Institute of Forensic Medicine at the University Medical Center Freiburg and were confirmed to contain five different known synthetic CBs.2 In North America, the first report of synthetic CBs being positively identified in incense products was made by the Customs and Border Protection – Chicago Laboratory.3 Five incense products were tested by GC/MS and found to contain small but verifiable amounts of HU-210 (Structure A), a known cannabinoid with a potency much greater than Δ9-tetrahydrocannabinol (THC) (Structure B).4,5 In another instance, the Wisconsin State Crime Laboratory identified an unknown white powder, suspected to be cocaine or methamphetamine, as the synthetic cannabinoid CP47,497 (Structure C).6 In an effort to determine the scope of this new designer drug phenomenon our lab has prepared several synthetic cannabinoids standards and developed an automated method to screen for and positively identify these compounds in commercial herbal incense products.

Synthetic CBs are a large family of structurally diverse compounds that bind to the same CB receptors in the brain as THC. There are two known CB receptors, CB1 and CB2. The CB1 receptor was discovered in 1988 and is found primarily in the central nervous system. It is believed to be responsible for the psychotropic effects of the cannabinoid agonists.7 The CB2 receptor was discovered in 1993 and is found mainly in the immune system.8

Efforts have been ongoing since the 1960s to find selective analogs of THC that separate beneficial effects, such as pain treatment, from psychotropic effects. Initial analogs of THC, also known as classical CBs, were closely related structural analogs and included HU-210 and Nabilone (Structure D) (Cesamet®, Lilly). Nabilone was approved in 1985 by the U.S. Food and Drug Administration (FDA) for treatment of chemotherapy-induced nausea and vomiting. The first generation of ‘non-classical’ cannabinoids (compounds lacking the partially reduced dibenzopyran ring) included a cyclohexylphenol (CP) series of compounds developed by Pfizer9-12 (which included compounds such as CP-47,497 and CP-55,940 (Structure E)) and the aminoalkylindole (AAI) series developed by a group at Sterling Winthrop.13 The most potent in this series was found to be WIN-55212-2 (Structure F). More recently, Huffman and co-workers have synthesized a large collection of analogs having a variety of core ring structures.14 Compounds in this series include as examples JWH 018 (Structure G), JWH 075 (Structure H), and JWH 019 (Structure I).

Resulting from a meeting of the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) on March 6, 2009, a report was generated to bring about awareness of the presence of these cannabinoids in certain incense products.15 The report concluded that almost nothing is known about the pharmacology, toxicology, and safety profile of these CBs in humans and that the potential for severe psychiatric complications or even life-threatening overdose are possible outcomes due to the variation in activity and quantity of CBs added. As a result of this report many European countries have made several of the synthetic CBs illegal and are actively pursuing legislation to control the use and sale of all CBs and incense products. In the United States there is currently no legislation preventing the sale of many of the synthetic CBs or their incense counterparts, however Missouri and other states are considering legislation to ban certain incense products.16 Due to the large variety of CBs available and wide range of activities, sensitive, automated screening methods will be necessary for routine positive identification of these synthetic CBs.

Figure 1. Classical and non-classical cannabinoids.

Automated Ion Trap Screening Method for the Detection of Synthetic Cannabinoids in Commercial Herbal Incense ProductsPaul D. Kennedy, Ph.D. & William Collin

Δ9-Tetrahydrocannabinol (THC) (B)HU-210 (A)

Nabilone (D) (−)-CP 55,940 (E) WIN 55212-2 (mesylate) (F)

JWH 018 (G) JWH 073 (H) JWH 019 (I)

CP 47,497 (C)

O N

O

O

H

HO

CH3

HH3C

CH3H3C

OH

OH

HO

OH

O

N

O

N

O• CH3SO3H

Cayman Chemical caymanchem.com caymanchem.com2 3

(-)-CP 55,940 90084[83002-04-4]MF: C24H40O3 FW: 376.6 Purity: ≥98% Supplied as: A crystalline solidSummary: A potent, non-selective CB receptor agonist with Ki values of 0.58 and 0.69 nM for human recombinant CB1 and CB2, respectively

5 mg $85.0010 mg $162.0025 mg $383.0050 mg $680.00

OH

OH

HO

OH

•Also Available: (±)-CP 55,940 (13241) EXCLUSIVE to CAYMAN (±)-5-epi CP 55,940 (13803) EXCLUSIVE to CAYMAN (+)-CP 55,940 (13608) EXCLUSIVE to CAYMAN

(±)-CP47,497 16851[70434-82-1]MF: C21H34O2 FW: 318.5 Purity: ≥98% Supplied as: A crystalline solidSummary: A cannabimimetic compound that binds the CB1 receptor with a Ki value of 2.2 nM

5 mg $50.0010 mg $95.0025 mg $225.0050 mg $400.00

OH

OH

•Also Available: (-)-CP 47,497 (13218) (+)-CP 47,497 (13219) (±)-CP 47,497-C8-homolog (13216) EXCLUSIVE to CAYMAN (±)-epi CP 47,497 (13801) EXCLUSIVE to CAYMAN (±)-3-epi CP 47,497-C8-homolog (13802) EXCLUSIVE to CAYMAN

HU-210 (DEA Schedule I Regulated Compound) 90082[112830-95-2]MF: C25H38O3 FW: 386.6 Purity: ≥98% Supplied as: A crystalline solidSummary: A potent CB1 and CB2 receptor agonist

1 mg $28.005 mg $126.0010 mg $224.0025 mg $490.00

O

OH

H

H

OH

HU-211 10006350[112924-45-5] DexanabinolMF: C25H38O3 FW: 386.6 Purity: ≥98% Supplied as: A crystalline solidSummary: A synthetic terpene-based CB devoid of CB1 and CB2 agonist activity; exhibits neuroprotective, antioxidant, and anti-inflammatory properties

1 mg $35.005 mg $158.0010 mg $280.0025 mg $613.00

O

OH

OH

H

H

HU-308 90086[256934-39-1] MF: C27H42O3 FW: 414.6 Purity: >98% Supplied as: A solution in methyl acetateSummary: a potent, selective agonist for the peripheral CB2 receptor

1 mg $23.005 mg $104.0010 mg $184.0025 mg $403.00

OH

O

O

Cannabinoid Ret. Time (min) Major MS Ion(s) (amu) Major MS/MS Ions (amu)

CP 55,940 10.2 415.2, 399.3, 359.3, 233.1 341.1, 233.1, 215.0, 147.0, 121.0

JWH 200 12.3 385.2 155.0, 145.0, 117.1

WIN 55212-2 14.4 427.2 155.0, 145.0, 127.0

CP 47,497 14.7 488.3*, 319.2, 301.2, 279.1 301.2, 233.1, 175.0, 107.1

CP 47,497 (CAY 10596) 16.4 488.3*, 355.3, 333.3, 315.3, 175.1 315.3, 247.2, 175.0, 107.1

JWH 015 16.9 328.2 200.0, 155.0, 145.0

JWH 250 17.5 336.2 188.1, 121.1

HU-210 18 488.3*, 409.3, 387.3 369.2, 261.1, 243.1, 201.0, 189.0

JWH 073 18.6 328.2 200.0, 155.0, 145.0, 117.0

HU-331 19.2 488.3*, 351.2, 329.2, 311.2 311.2, 287.1, 273.1, 259.1, 209.1

JWH 018 20.2 342.2 214.1, 155.0, 145.0, 117.1

JWH 019 21.8 356.2 228.1, 155.0, 145.0, 117.1

HU-308 23.7 488.3*, 447.2, 437.2, 415.3, 397.3 355.2, 303.2, 277.2, 271.1, 215.0, 133.0

ResultsThe successful use of MSn libraries for the screening and identification of large numbers of target analytes has been demonstrated previously.17 In this approach a standardized HPLC method is used in order to match retention times with known standards and both MS and MS/MS spectra are generated under reproducible conditions18 and imported into a searchable mass spectral library database. It is important that the MS/MS spectra are reproducible as the spectral matching algorithm used for the library search compares the ions of the mass spectra as well as their relative intensities. Ion Trap MS is ideally suited for this application because fragmentation occurs in discrete stages and can be carefully controlled at each stage. The steps involve isolation of a target m/z, applying a tunable Fragmentation Amplitude voltage which very selectively fragments only the isolated mass, followed by detection of the resulting fragment ion mass spectrum. Positive identification requires that the retention time, MS, and MS/MS spectra all match within predefined limits.

In the present study, 13 commercially available synthetic CBs were included in the screening method (Table 1). A standard mixture of these 13 compounds was used to optimize the HPLC separation on an Agilent Technologies 1100 HPLC-DAD equipped with an Agilent 1100 MSD/Trap SL (model G2445A). Complete baseline separation was achieved for all 13 compounds under gradient conditions with a total run time of 30 minutes (Figure 2). MS and MS/MS spectra were generated using the Auto MSn and SmartFrag features of the Bruker LC-MSD/Trap control software (v.4.1). Auto MSn is a data-dependent acquisition feature in which MS/MS fragmentation is automatically triggered for any ion exceeding a predetermined threshold. For this study only the target masses were included in the data-dependent acquisition. The SmartFrag feature automatically ramps the Fragmentation Amplitude which maximizes the distribution of product ions. This feature precludes the need to optimize collision energies for each analyte of interest.

The spectral library was generated by injecting standards of each CB under the optimized experimental conditions. For each standard, both MS and MS/MS spectra were collected and imported into the Bruker Library Editor Software (v.2.1). The major ions of each MS stage for each CB standard are listed in Table 1. A nice feature of the Library Editor software is the ability to edit the searchable mass list of each recorded spectra. In several of the MS spectra an unknown impurity mass of 488.3 m/z was observed. This mass was removed from the spectra with the expectation that this would improve library search results. As a validation of the library screening the original cannabinoid standard mixture was analyzed and searched against the library. Spectra in the sample are compared against the library spectra quantitatively by the calculation of Fit, Reverse Fit (RFit), and Purity values – normalized to a 0-1000 scale with 1000 being a perfect match. Fit values represent how well the library spectra match the acquired spectra, RFit values represent how well acquired spectra match the library spectra and the Purity calculation is a combination of these. For the test screening of the standard mixture Purity values were in the range of 872-1000 for all but two CBs, demonstrating very high levels of matching between analyte and library spectra. CP 47,497-C8 was identified in Spike99 and exSES with Purity values of 746 and 691, respectively, and CP 47,497 was manually detected in exSES. The lower Purity values are attributed to poorer sensitivity of these two compounds and poor stability in the mass spectrometer resulting in non-specific fragmentation and poor MS spectra reproducibility. This suggests that for samples containing low levels of these compounds the current library search method may not be sufficient. In this study the presence/absence of these two compounds was confirmed by manual inspection of the data. Efforts to improve this limitation are ongoing.

With a method in-hand, five incense products were purchased for testing. Incense brand names tested include K2, Tribal Warrior, Spike99, exSES, and Neder Gold. Extraction of these samples was carried out very rapidly in parallel using a Precellys 24 homogenizer. Approximately 100 mg of each incense sample was weighed into a 2 ml Precellys tube containing 2.8 mm ceramic beads. To each sample, 1.5 ml of ethanol was added and the extractions were carried out using a preprogrammed method – 2 x 20 second extractions (30 second inter-delay time) at 6500 rpm was sufficient to fully

Table 1. Commercially available synthetic CBs and major ions observed in MS and MS/MS library spectra

Figure 2. HPLC chromatogram of the synthetic cannabinoid standard mixture

1

2

3

6

7 8

9 11 12

13

4 5 10

SIG10037.D: UV Chromatogram, 225.16 nm

0 5 10 15 20 25 Time (min)

0

100

200

300

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Intens.Cannabinoid Standard Mix1. CP 55,9402. JWH-2003. WIN 55212-24. CP 47,4975. CP 47,497-C86. JWH-0157. JWH-2508. HU-2109. JWH-07310. HU-33111. JWH-01812. JWH-01913. HU-308

*unknown impurity

Cayman Chemical caymanchem.com caymanchem.com4 5

328.2

350.2 550.7

677.1

SIG10069.D: +MS, 18.5-18.9min (#1027-#1051)

100 200 300 400 500 600 700 m/z0.0

0.5

1.0

1.5

8x10Intens.

328.2

677.0

SIG10069.D: Cannabinoids: JWH 073; IT ESI +MS (P: 663, F: 663, R: 663, M: 1000)

200 300 400 500 600 700m/z0

200

400

600

800

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Intens.

117.1

155.0

200.0

SIG10069.D: +MS2(328.2), 18.5-18.9min (#1028-#1052)

100 200 300 400 500 600 700 m/z0

1

2

3

7x10Intens.

145.0

155.0

200.0

SIG10069.D: Cannabinoids: JWH 073; IT ESI +MS2(328.185) (P: 999, F: 999, R: 999, M: 1000)

120 140 160 180 200 220 240 260 m/z0

200

400

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Intens.

385.2

423.1

SIG10069.D: +MS, 11.9-12.3min (#658-#682)

100 200 300 400 500 600 700 m/z0.0

0.2

0.4

0.6

0.8

1.0

8x10Intens.

385.2

423.1

SIG10069.D: Cannabinoids: JWH 200; IT ESI +MS (P: 526, F: 526, R: 526, M: 1000)

200 300 400 500 600 700 m/z0

200

400

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800

1000

Intens.

155.0

298.1

SIG10069.D: +MS2(385.2), 11.9-12.3min (#659-#683)

100 200 300 400 500 600 700 m/z0

2

4

6

7x10Intens.

145.0

155.0

298.1

SIG10069.D: Cannabinoids: JWH 200; IT ESI +MS2(385.061) (P: 996, F: 996, R: 996, M: 1000)

150 200 250 300 350 400 m/z0

200

400

600

800

1000

Intens.

242.3

342.2

550.6

705.1

SIG10069.D: +MS, 19.9-20.3min (#1113-#1137)

100 200 300 400 500 600 700 m/z0.0

0.5

1.0

1.5

2.0

8x10Intens.

342.2

705.0

SIG10069.D: Cannabinoids: JWH 018; IT ESI +MS (P: 705, F: 722, R: 705, M: 1000)

200 300 400 500 600 700 m/z0

200

400

600

800

1000

Intens.

155.0

214.1

SIG10069.D: +MS2(342.2), 19.9-20.3min (#1114-#1138)

100 200 300 400 500 600 700 m/z0

1

2

3

4

7x10Intens.

155.0

214.1

SIG10069.D: Cannabinoids: JWH 018; IT ESI +MS2(342.177) (P: 997, F: 997, R: 997, M: 1000)

150 200 250 300 350 400 450 m/z0

200

400

600

800

1000

Intens.

Cannabinoid K2 Tribal Warrior Spike99 exSES Neder Gold

CP 55,940

JWH 200 + (872)

WIN 55212-2

CP 47,497 + (manual detect)*

CP 47,497 (CAY 10596) + (746)* + (691)*

JWH 015

JWH 250 + (947) + (991)

HU-210

JWH 073 + (912) + (975) + (928)

HU-331

JWH 018 + (922) + (938) + (912)

JWH 019 + (982)

HU-308

EXCLUSIVE to CAYMAN

HU-331 10005673[137252-25-6]MF: C21H28O3 FW: 328.5 Purity: ≥95% Supplied as: A solution in methyl acetateSummary: A hydroxylquinone CB analog that exhibits potent antineoplastic activity on a variety of human cancer cell lines

1 mg $48.005 mg $216.0010 mg $384.0025 mg $840.00 HO

O

O

JWH 015 10009018[155471-08-2]MF: C23H21NO FW: 327.4 Purity: ≥98% Supplied as: A crystalline solidSummary: A selective CB2 receptor agonist with Ki values of 13.8 and 383 nM for human recombinant CB2 and CB1 receptors, respectively

1 mg $11.005 mg $50.0010 mg $88.0025 mg $193.00 O N

EXCLUSIVE to CAYMAN

JWH 018 13169[209414-07-3]MF: C24H23NO FW: 341.5 Purity: ≥98%Supplied as: A solution in methyl acetateSummary: A selective agonist of the CB1 receptor with Ki values of 9.0 and 2.94 nM for CB1 and CB2 respectively

5 mg $50.0025 mg $225.00100 mg $700.001 g $4,500.00

O N

Compound Retention Time (min) MS(n) Isol. m/z Compound Name Library Retention Time (min) Fit’ RFit’ Purity’

1 12.1 385.2 JWH 200 12.3 872 872 872

2 18.7 328.2 JWH 073 18.6 912 912 912

3 20.1 342.2 JWH 018 20.2 927 922 922

Table 2. Summary of library screening results for incense products

* The suspected trans isomers, which are known byproducts in the syntheses of these compounds, were also detected.

Figure 3. K2 Library search report

homogenize and extract the samples. Each sample was then filtered and washed with 3 x 1 ml aliquots of ethanol. The combined ethanol washes were then blown to dryness under a gentle stream of nitrogen, reconstituted in 1 ml of acetonitrile and filtered through a 13 mm x 2.5 um PTFE syringe filter. A final injection volume of 10 ul was used in the analysis.

Of the five incense samples analyzed, four tested positive for the presence of one or more of the library CBs. A summary of the results is shown in Table 2. An example of the typical data observed can be demonstrated for the K2 sample. The software automatically searches the total ion chromatogram (TIC) and identifies the Auto MSn peaks over the retention time range of the target analytes. This peak list is then searched against the CB library and the resulting peak table contains an unfiltered list of possible hits. Since the software does not currently remove hits that do not match by retention time, these hits are removed manually along with any remaining questionable false positives or low purity results. The resulting compound list has been set up to include the compound name of each positive hit as well as Fit, RFit, and Purity values. From the results a final report is generated that includes the TIC chromatogram, compound list, MS, and MS/MS spectra of each identified analyte and all corresponding library spectra. The final report for the K2 sample, including Mass Spectral Data for Compound 3 as an example, is shown in Figure 3.

It can be seen from Table 2 that four out of the five incense samples tested positive for multiple synthetic CBs. The K2 incense product contained JWH 200, JWH 073, and JWH 018 at very high levels. Tribal Warrior contained a very high level of JWH 018 and much lower levels of CP 47,497-C8, JWH 250, and JWH 073. Spike99 contained the largest number of synthetic cannabinoids and included high levels of JWH 250, JWH 073, and JWH 018 along with lower levels of CP 47,497-C8 and JWH 019. The Neder Gold sample did not yield any positive hits upon analysis. Further investigation is ongoing to apply this methodology to new incense samples, to increase the sensitivity of the current method and to produce additional standards to aid in quantitative health risk assessment studies.

Compound 3

Sample MS

Library MS

Sample MS/MS

Library MS/MS

0 5 10 15 20 25 Time [min]0

2

4

6

8

8x10Intens.

Cayman Chemical caymanchem.com caymanchem.com6 7

References1. Unpublished data available online at http://usualredant.de/drogen/download/analyse- the-phar-spice-jwh-018.pdf 2. Auwarter. V.; Dresen, S.; Weinmann, W.; Muller, M.; Putz, M.; Ferreiros, N. J. Mass Spectrom. 2009, 44, 832.3. The Drug Enforcement Administration, Office of Forensic Sciences, Microgram Bulletin March 2009, pp. 23-24. 4. Mechoulam, R.; Feigenbaum; Lander; Segal; Järbe; Hiltunen; Consroe Experientia 1988, 44(9), 762. 5. Devane, W. A.; Breuer; Sheskin; Järbe; Eisen; Mechoulam J. Med Chem 1992, 35 (11), 2065.6. The Drug Enforcement Administration, Office of Forensic Sciences, Microgram Bulletin December 2009, page 89.7. Devane, W. A.; Dysarz, F. A.; Johnson, M. R.; Melvin, L. S.; Howlett, A. C. Mol. Pharmacol. 1988, 34, 605.8. Munro, S.; Thomas, K. L.; Abu-Shaar, M. Nature 1993, 365, 61.9. Melvin, L. S.; Johnson, M. R.; Herbert, C. A.; Milne, G. M.; Weissman, A. A. J. Med. Chem.1984, 27, 67. 10. Melvin, L. S.; Johnson, M. R.; Milne, G. M. Life Sci. 1982, 31, 1703. 11. Melvin, L. S.; Johnson, M. R. Cannabinoids as Therapeutic Agents; Mechoulam, R.; Ed; CRC Press; Boca Raton, FL; 1986; pp 121-145. 12. Melvin, L. S.; Johnson, M. R.; Milne, G. M.; Subramian, B.; Wilken, G. H.; Howlett, A. C. Mol. Pharmacol. 1993, 44, 1008.13. Bell, M. R.; D’Ambra, T. E.; Kumar, V.; Eissanstat, M. A.; Herrmann, J. L.; Wetzel, J. R.; Rosi, D.; Philion, R. E.; Daum, S. J.; Hlasta, D. J.; Kullnig, R. K.; Ackerman, J. H.; Haubrich, D. R.; Luttinger, D. A.; Baizman, E. R.; Miller, M. S.; Ward, S. J. J. Med. Chem. 1991, 34, 1099.14. Huffman, J. W.; Dai, D.; Martin, B. R.; Compton, D. R. Bioorg. Med. Chem. Lett. 1994, 4, 563. Wiley, J. L.; Compton, D. R.; Dai, D.; Lainton, J. A. H.; Phillips, M.; Huffman, J. W.; Martin, B. R. J. Pharmacol. Exp. Ther. 1998, 285, 995. Huffman, J. W. Current Pharm. Design 2000, 6, 1323.15. “Understanding the ‘Spice’ Phenomenon”, European Monitoring Centre for Drugs and Drug Addiction ©2009. 16. News report from www.emissourian.com Feb. 24, 2010.17. Mueller, C. A.; Weinmann, W.; Dresen, S.; Schreiber, A.; Gergov, M. Rapid Communications in Mass Spectrometry 2005, 19, 1332.18. MS Conditions: positive ESI mode, 350 °C Dry temp, 70psi Nebulizer, 12L/min Dry gas, 43.0 Trap Drive, 100-800m/z mass range, 5 spectra averaging, Charge Control On, 300ms Max Accum. Time, 30000 ICC target, Auto MS/MS on, 100,000 Auto MS/MS Threshold, SmartFrag on, 4.0m/z Isolation Width.

Custom SynthesisCayman has experienced, highly skilled chemists on staff that can synthesize a diverse range of high purity compounds in milligram to multi-gram to process scale batches. We routinely perform custom syntheses of a variety of unique, and often complex biomolecules including cannabinoid and endocannabinoid products. All regulated items require proper authorization.

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Contract Analytical Services• Experienced staff of dedicated analytical chemists.

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• GC-FID volatiles analysis, USP residual solvents testing, and analytical reference standard qualification.

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• Many of our services are also maintained under GMP guidelines –please call for additional information.

For more information on any of these services please contact our sales department at

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JWH 019 13633[209414-08-4] MF: C25H25NO FW: 355.5 Purity: ≥98% Supplied as: A crystalline solidSummary: A cannabimimetic indole that shows high-affinity for both CB1 (Ki = 9.8 nM) and CB2 (Ki =5.6 nM)

5 mg $55.0010 mg $105.0025 mg $248.00100 mg $880.00 O N

EXCLUSIVE to CAYMAN

JWH 073 13170[208987-48-8]MF: C23H21NO FW: 327.4 Purity: ≥97%Supplied as: A solution in methyl acetateSummary: A selective agonist of the CB1 receptor with Ki values of 8.9 and 38 nM for CB1 and CB2 respectively

5 mg $50.0025 mg $225.00100 mg $700.001 g $4,500.00

O N

JWH 200 13171[103610-04-4]MF: C25H24N2O2 FW: 384.5 Purity: ≥98% Supplied as: A crystalline solidSummary: An aminoalkylindole that acts as a CB receptor ligand, binding the CB1 receptor with high-affinity (IC50 = 7.8 - 42 nM)

5 mg $55.0025 mg $248.00100 mg $770.001 g $4,950.00

O NN

O

JWH 250 13634[864445-43-2]MF: C22H25NO2 FW: 335.2 Purity: ≥98% Supplied as: A crystalline solidSummary: A cannabimimetic indole that shows high-affinity for both CB1 (Ki = 11 nM) and CB2 (Ki = 33 nM)

5 mg $73.0025 mg $329.00100 mg $1,022.001 g $6,570.00

O NO

WIN 55212-2 (mesylate) 10009023[131543-23-2]MF: C27H26N2O3 • CH4SO3 FW: 522.6 Purity: ≥98%Supplied as: A crystalline solidSummary: A potent aminoalkylindole CB receptor agonist with Ki values of 3.3 and 62.3 nM for human recombinant CB1 and CB2 receptors, respectively

5 mg $30.0010 mg $57.0025 mg $135.0050 mg $240.00

O

N

O

N

O• CH3SO3H

Cayman Chemical caymanchem.com8

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