THJ-2201
Synthetic cannabinoid
- CA: Schedule II
- DE: Anlage II (Authorized trade only, not prescriptible)
- UK: Class B
- US: Schedule I
- [1-(5-Fluoropentyl)-1H-indazol-3-yl](1-naphthyl)methanone
- 1801552-01-1 Y
- 91864533
- 30646749
- D7P051IW0T
- DTXSID901010029
- Interactive image
- c1ccc2c(c1)cccc2C(=O)c3c4ccccc4n(n3)CCCCCF
InChI
- InChI=1S/C23H21FN2O/c24-15-6-1-7-16-26-21-14-5-4-12-20(21)22(25-26)23(27)19-13-8-10-17-9-2-3-11-18(17)19/h2-5,8-14H,1,6-7,15-16H2
- Key:DULWRYKFTVFPTL-UHFFFAOYSA-N
THJ-2201 is an indazole-based synthetic cannabinoid that presumably acts as a potent agonist of the CB1 receptor and has been sold online as a designer drug.[1][2][3][4]
It is a structural analog of AM-2201 in which the central indole ring has been replaced by indazole.[5]
Pharmacology
THJ-2201 acts as a full agonist with a binding affinity of 1.34 nM at CB1 and 1.32 nM at CB2 cannabinoid receptors.[6]
Side effects
THJ-2201 has been linked to at least one hospitalization and death due to its use.[7]
Legal status
Because of the hazards associated with recreational use of this compound,[8] it is classified as a Schedule I controlled substance in the United States.[9]
It is also an Anlage II controlled drug in Germany.[10]
See also
- AM-694
- AM-1235
- AM-2232
- AM-2233
- FUBIMINA
- JWH-018
- List of AM cannabinoids
- List of JWH cannabinoids
- NM-2201
- THJ-018
References
- ^ Diao X, Wohlfarth A, Pang S, Scheidweiler KB, Huestis MA (January 2016). "High-Resolution Mass Spectrometry for Characterizing the Metabolism of Synthetic Cannabinoid THJ-018 and Its 5-Fluoro Analog THJ-2201 after Incubation in Human Hepatocytes". Clinical Chemistry. 62 (1): 157–169. doi:10.1373/clinchem.2015.243535. PMID 26430074.
- ^ Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Morzherin Y, Shafran Y (September 2014). "3-Naphthoylindazoles and 2-naphthoylbenzoimidazoles as novel chemical groups of synthetic cannabinoids: chemical structure elucidation, analytical characteristics and identification of the first representatives in smoke mixtures". Forensic Science International. 242: 72–80. doi:10.1016/j.forsciint.2014.06.022. PMID 25036783.
- ^ Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T (August 2014). "Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products". Forensic Toxicology. 32 (2): 266–281. doi:10.1007/s11419-014-0238-5. S2CID 11873421.
- ^ Diao X, Scheidweiler KB, Wohlfarth A, Zhu M, Pang S, Huestis MA (2016). "Strategies to distinguish new synthetic cannabinoid FUBIMINA (BIM-2201) intake from its isomer THJ-2201: metabolism of FUBIMINA in human hepatocytes". Forensic Toxicology. 34 (2): 256–267. doi:10.1007/s11419-016-0312-2. PMC 4971051. PMID 27547265.
- ^ "THJ-2201". Cayman Chemical. Retrieved 21 July 2015.
- ^ Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE (1 July 2016). "Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice". Forensic Toxicology. 34 (2): 329–343. doi:10.1007/s11419-016-0320-2. PMC 4929166. PMID 27429655.
- ^ Trecki J, Gerona RR, Schwartz MD (July 2015). "Synthetic Cannabinoid-Related Illnesses and Deaths". The New England Journal of Medicine. 373 (2): 103–107. doi:10.1056/NEJMp1505328. PMID 26154784.
- ^ Drug and Chemical Evaluation Section, Office of Diversion Control, Drug Enforcement Administration (December 2014). N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-1H-indazole-3- carboxamide (AB-CHMINACA), N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H- indazole-3-carboxamide (AB-PINACA) and [1-(5-fluoropentyl)-1H-indazol-3- yl](naphthalen-1-yl)methanone (THJ-2201): Background Information and Evaluation of 'Three Factor Analysis' (Factors 4, 5, and 6) for Temporary Scheduling (PDF) (Report). Archived from the original (PDF) on 2018-09-27. Retrieved 2015-04-05.
- ^ Drug Enforcement Administration Do (January 2015). "Schedules of controlled substances: temporary placement of three synthetic cannabinoids into schedule I. Final order". Federal Register. 80 (20): 5042–5047. PMID 25730924.
- ^ "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)". Retrieved 9 July 2015.
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(comparison)
Cannabibutols |
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Cannabichromenes | |
Cannabicyclols |
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Cannabidiols | |
Cannabielsoins |
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Cannabigerols | |
Cannabiphorols |
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Cannabinols | |
Cannabitriols |
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Cannabivarins |
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Delta-8-tetrahydrocannabinols |
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Delta-9-tetrahydrocannabinols | |
Delta-10-Tetrahydrocannabinols | |
Miscellaneous cannabinoids |
|
Active metabolites |
- Arachidonoyl ethanolamide (AEA; anandamide)
- 2-Arachidonoylglycerol (2-AG)
- 2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
- 2-Oleoylglycerol (2-OG)
- N-Arachidonoyl dopamine (NADA)
- N-Arachidonylglycine (NAGly)
- 2-Arachidonoyl lysophosphatidylinositol (2-ALPI)
- N-Arachidonoyl serotonin (AA-5-HT)
- Docosatetraenoylethanolamide (DEA)
- Lysophosphatidylinositol (LPI)
- Oleamide
- Oleoylethanolamide (OEA)
- Palmitoylethanolamide (PEA)
- RVD-Hpα
- Stearoylethanolamide (SEA)
- O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids (dibenzopyrans) |
|
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Non-classical cannabinoids |
|
Adamantoylindoles |
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Benzimidazoles | |
Benzoylindoles |
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Cyclohexylphenols | |
Eicosanoids |
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Hydrocarbons | |
Indazole carboxamides | |
Indazole-3- carboxamides |
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Indole-3-carboxamides |
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Indole-3-carboxylates | |
Naphthoylindazoles |
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Naphthoylindoles |
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Naphthoylpyrroles | |
Naphthylmethylindenes | |
Naphthylmethylindoles | |
Phenylacetylindoles | |
Pyrazolecarboxamides |
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Pyrrolobenzoxazines | |
Quinolinyl esters | |
Tetramethylcyclo- propanoylindazoles | |
Tetramethylcyclo- propanoylindoles | |
Tetramethylcyclo- propylindoles | |
Others |
|
enhancers
(inactivation inhibitors)
- 4-Nonylphenylboronic acid
- AM-404
- Arachidonoyl serotonin
- Arvanil
- BIA 10-2474
- Biochanin A
- CAY-10401
- CAY-10429
- Genistein
- Guineesine
- IDFP
- JNJ 1661010
- JNJ-42165279
- JZL184
- JZL195
- Kaempferol
- LY-2183240
- MK-4409
- O-1624
- O-2093
- Oleoylethanolamide (OEA)
- Olvanil
- Palmitoylethanolamide (PEA)
- PF-04457845
- PF-622
- PF-750
- PF-3845
- PHOP
- URB-447
- URB-597
- URB-602
- URB-754
- VDM-11
(antagonists/inverse
agonists/antibodies)
- AM-251
- AM-281
- AM-630
- AM-1387
- AM-4113
- AM-6527
- AM-6545
- BML-190
- Brizantin (Бризантин)
- CAY-10508
- CB-25
- CB-52
- CB-86
- Dietressa (Диетресса)
- Drinabant (AVE1625)
- Hemopressin
- Ibipinabant (SLV319)
- JTE-907
- LH-21
- LY-320,135
- MDA-77
- MJ-15
- MK-9470
- NESS-0327
- NIDA-41020
- O-606
- O-1184
- O-1248
- O-1918
- O-2050
- O-2654
- Otenabant (CP-945,598)
- PF-514273
- PipISB
- PSB-SB-487
- Rimonabant (SR141716)
- Rosonabant (E-6776)
- SR-144,528
- Surinabant (SR147778)
- Taranabant (MK-0364)
- TM-38837
- VCHSR
- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics