THJ-2201

THJ-2201
Legal status
Legal status	CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name [1-(5-Fluoropentyl)-1H-indazol-3-yl](1-naphthyl)methanone;
CAS Number	1801552-01-1 ;
PubChem CID	91864533;
ChemSpider	30646749;
UNII	D7P051IW0T;
CompTox Dashboard (EPA)	DTXSID901010029 ;
Chemical and physical data
Formula	C23H21FN2O
Molar mass	360.432 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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It is a structural analog of AM-2201 in which the central indole ring has been replaced by indazole.^[5]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]

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.

[1] 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.

[2] 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.

[3] 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.

[4] 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.

[5] "THJ-2201". Cayman Chemical. Retrieved 21 July 2015.

[6] 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.

[7] 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.

[8] 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.

[9] 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.

[10] "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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Pharmacology

Side effects

Legal status

See also

References