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FACT SHEET

THJ-2201  

(AM‐2201 indazole analogue) 

March 2017

Dr. Apr. Peter Blanckaert Coordinator Belgian Early Warning System on Drugs DO Public Health&Surveillance, Drugs Program (BMCDDA) Juliette Wytsmanstraat 14 | 1050 Brussels  

Institut Scientifique de Santé Publique Wetenschappelijk Instituut Volksgezondheid Scientific Institute of Public Health www.wiv‐isp.be 

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A. General information Created March 2017 Type Narcotic drugs Group Cannabinoids Name AM-2201 indazole analogue, THJ-2201 Nature of substance This is a naphthoylindazole substance and is closely related to the known synthetic cannabinoid receptor agonist AM-2201 (Am-2201 is the fluoropentyl derivative of JWH-018). Systematic chemical name [1-(5-fluoropentyl)-1H-indazol-3-yl](naphthalen-1-yl)methanone Other names 5F-JWH-018-N, 5F-THJ-018, THJ-2201

B. Alerts Seizures have been reported in a.o.:

Norway, Slovakia, Cyprys in 2015 Slovenia, Lithuania, Denmark, France, Hungary, Romania, Sweden, Germany,

UK in 2014 Latvia, Finland, Sweden in 2013

C. Pictures

Figure: Collected powder sample in Germany

D. Clinical information Usage Very little, if any information is available in scientific literature with regard to specific use or risks concerining THJ-2201.Since the substance is a synthetic cannabinoid receptor agonist, this substance is used in herbal mixtures to mimic the effects of natural cannabis or THC (“synthetic cannabis”). Health risks No information whatsoever with regard to the toxicity of this compound is present, neither short or long term. Consequently, no specific treatments for intoxications with this compound are available. Since most intoxications with synthetic cannabinoids results in mental symptoms such as increased anxiety, paranoia and psychosis, it is to be expected this will also be the case for intoxications involving THJ-2201. Clinical intoxication symptoms include encephalopathy, mydriasis, hypertonia and hyperexcitability. Treatment is symptomatic. Other uses None known.

E. Legal status Denmark: controlled Estonia: controlled Germany: controlled Hungary: controlled Slovenia: controlled Turkey: controlled JAPAN: Controlled since 25 August 2014 USA - since 20 January 2015 Belgium:

F. Chemistry Systematic chemical name [1-(5-fluoropentyl)-1H-indazol-3-yl](naphthalen-1-yl)methanone Other names 5F-JWH-018-N, 5F-THJ-018, THJ-2201 Other chemical names and variants Unknown Chemical Abstracts Service (CAS) registry number 1801552-01-1

Molecular information Molecular structure:

Molecular formula: C23H21FN2O Molecular weight: 360.4240g/mol Synthesis, manufacture and precursors No information. Physical description White/crystalline powder/crystals Identification and analytical profile can be found at the end of this document and were kindly provided by the Hungarian, German, Swedish, Latvian and Finnish focal points.

G. References Pfizer Inc., Indazole derivatives WO 2009106980 A2 http://www.google.com/patents/WO2009106980A2?cl=en

File :C:\Daten Filou\Januar 14\F1400199.DOperator : AVAcquired : 30 Jan 2014 17:44 using AcqMethod B-HyAC.MInstrument : GC_MS_1Sample Name: THJ-2201 Misc Info : Vial Number: 13

4.00 5.00 6.00 7.00 8.00 9.00 10.00 11.00 12.00 13.00 14.00 15.00 16.00 17.00 18.00 19.00

100000

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700000

800000

900000

1000000

1100000

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1300000

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Time-->

Abundance TIC: F1400199.D\data.ms

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

10000

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30000

40000

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m/z-->

Abundance Scan 1521 (13.101 min): F1400199.D\data.ms (-2096) (-)360.2

271.1

127.1

155.0

285.1257.1

77.1340.2213.1103.0 243.1 311.2142.1

90.051.0 185.1 230.1199.0171.064.0 298.1 327.1

30405060708090100110120130140150160170180190 ppm

22.33

22.36

29.30

29.61

29.74

39.59

39.73

39.87

40.01

40.15

40.26

40.29

40.40

40.43

40.55

49.36

83.52

84.60

111.33

122.37

123.70

124.53

125.14

125.57

126.75

127.56

127.58

128.91

128.97

130.69

131.45

133.67

136.73

141.08

142.20

191.53

Current Data ParametersNAME Tibi_THJ2201EXPNO 2PROCNO 1

F2 - Acquisition ParametersDate_ 20140526Time 12.20INSTRUM spectPROBHD 5 mm CPTCI 1H-PULPROG jmodTD 32768SOLVENT DMSONS 583DS 16SWH 42613.637 HzFIDRES 1.300465 HzAQ 0.3844779 secRG 203DW 11.733 usecDE 18.00 usecTE 300.0 KCNST2 145.0000000CNST11 1.0000000D1 1.50000000 secD20 0.00689655 secTD0 1

======== CHANNEL f1 ========SFO1 150.9370112 MHzNUC1 13CP1 11.00 usecP2 22.00 usecPLW1 129.00000000 W

======== CHANNEL f2 ========SFO2 600.2024008 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 70.00 usecPLW2 5.00000000 WPLW12 0.16718000 W

F2 - Processing parametersSI 65536SF 150.9204100 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40

Current Data ParametersNAME Tibi_THJ2201EXPNO 1PROCNO 1

F2 - Acquisition ParametersDate_ 20140526Time 12.14INSTRUM spectPROBHD 5 mm CPTCI 1H-PULPROG zg30TD 32768SOLVENT DMSONS 32DS 16SWH 12019.230 HzFIDRES 0.366798 HzAQ 1.3631488 secRG 22.6DW 41.600 usecDE 10.00 usecTE 300.0 KD1 2.00000000 secTD0 1

======== CHANNEL f1 ========SFO1 600.2036012 MHzNUC1 1HP1 9.00 usecPLW1 5.00000000 W

F2 - Processing parametersSI 65536SF 600.2000018 MHzWDW EMSSB 0LB 0 HzGB 0PC 1.00

1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5 ppm

1.292

1.300

1.313

1.568

1.581

1.593

1.611

1.624

1.636

1.812

1.825

1.837

2.517

2.520

2.523

3.293

4.298

4.308

4.319

4.378

4.388

4.398

4.490

4.502

4.513

7.445

7.457

7.470

7.535

7.547

7.561

7.574

7.580

7.587

7.592

7.605

7.628

7.641

7.653

7.888

7.900

7.903

7.917

8.051

8.064

2.10

2.10

2.09

1.04

1.05

2.08

1.06

3.12

1.04

2.05

2.04

1.02

1.00

THJ-2201

30

35

40

45

50

55

60

65

70

75

80

85

90

95

%T

1000 1500 2000 2500 3000 3500

Wellenzahlen (cm-1)

ATR-IR: THJ-2201 (AM-2201-Indazolanalog) solid

66

9,3

72

5,8

74

9,7

77

7,0

79

1,4

81

7,2

85

3,8

86

0,8

89

0,2

91

6,7

92

9,0

95

0,3

97

9,9

10

08

,9

10

24

,2

10

47

,0

10

64

,01

07

4,0

10

93

,6

11

12

,31

12

3,0

11

38

,0

11

51

,31

16

5,7

11

84

,2

12

06

,3

12

33

,11

24

3,9

12

66

,21

27

6,0

13

14

,1

13

40

,1

13

66

,11

38

0,1

13

90

,01

40

0,3

14

12

,5

14

34

,8

14

58

,01

46

6,1

14

94

,11

50

6,6

15

75

,0

15

93

,216

13

,1

16

42

,7

THJ-2201

25

30

35

40

45

50

55

60

65

70

75

80

85

90

95

%T

800 1000 1200 1400 1600 1800

Wellenzahlen (cm-1)

ATR-IR: THJ-2201 (AM-2201-Indazolanalog, solid, Ausschnitt)

THJ-2201 (neat)

66

68

70

72

74

76

78

80

82

84

86

88

90

92

94

96

98

100%

T

500 1000 1500 2000 2500 3000 3500 4000

Wellenzahlen (cm-1)

ATR-IR: THJ-2201 (AM-2201-Indazolanalog) neat

65

1,9

66

8,1

69

2,6

69

8,7

75

1,0

77

8,1

79

0,7

81

4,8

86

4,7

89

3,9

91

1,1

93

1,59

59

,5

98

2,4

10

07

,41

02

2,9

10

62

,4

10

93

,5

11

39

,1

11

71

,1

12

30

,3

12

59

,51

27

5,1

13

17

,0

13

42

,2

13

68

,7

13

89

,0

14

12

,8

14

68

,3

14

93

,81

50

8,0

15

77

,11

59

1,8

16

40

,1

16

98

,4

THJ-2201 (neat)

64

66

68

70

72

74

76

78

80

82

84

86

88

90

92

94

96

98

100%

T

800 1000 1200 1400 1600 1800

Wellenzahlen (cm-1)

ATR-IR: THJ-2201 (AM-2201-Indazolanalog, neat, Ausschnitt)

THJ-2201 #1097 RT: 21,99 AV: 1 SB: 2 21,59 , 22,72 NL: 2,89E7T: + c EI Q3MS [ 29,00-600,00]

50 100 150 200 250 300 350

m/z

0

5

10

15

20

25

30

35

40

45

50

55

60

65

70

75

80

85

90

95

100

Rela

tive A

bundance

271

360127

359

155

272

285

257 361

128156126 131

25624377 213 258 28641 14210390 299 36275 157 24118943 117 34439 185 31163 199 331 380

THJ-2201

AM-2201 Indazolanalog

C23H21FN2O

MW: 360

RI: 3075 (DB-1) N

N

O

F