THJ-2201

THJ-2201
Legal status
Legal status	CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); 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;
CompTox Dashboard (EPA)	DTXSID901010029 ;
Chemical and physical data
Formula	C23H21FN2O
Molar mass	360.42 g/mol 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It is a structural analog of AM-2201 in which the central indole ring has been replaced by indazole.^[5]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 1.34nM at CB₁ and 1.32nM 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

^ Xingxing Diao; Ariane Wohlfarth; Shaokun Pang; Karl B. Scheidweiler; Marilyn A. Huestis (October 2015). "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. doi:10.1373/clinchem.2015.243535. PMID 26430074.
^ Shevyrin, Vadim; Melkozerov, Vladimir; Nevero, Alexander; Eltsov, Oleg; Morzherin, Yuri; Shafran, Yuri (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.
^ Nahoko Uchiyama; Yoshihiko Shimokawa; Maiko Kawamura; Ruri Kikura-Hanajiri; Takashi Hakamatsuka (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.
^ Xingxing Diao; Karl B. Scheidweiler; Ariane Wohlfarth; Mingshe Zhu; Shaokun Pang; Marilyn A. Huestis (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: 256–267. doi:10.1007/s11419-016-0312-2.
^ "THJ-2201". Cayman Chemical. Retrieved 21 July 2015.
^ Hess, Cornelius; Schoeder, ClaraT.; Pillaiyar, Thanigaimalai; Madea, Burkhard; Müller, ChristaE. (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. ISSN 1860-8965. PMC 4929166. PMID 27429655.
^ Jordan Trecki; Roy R. Gerona; Michael D. Schwartz (July 2015). "Synthetic Cannabinoid–Related Illnesses and Deaths". 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). {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)
^ Drug Enforcement Administration, Department of Justice (2015). "Schedules of controlled substances: Temporary placement of three synthetic cannabinoids into schedule I. Final order". Federal register. 80 (20): 5042–7. 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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[1] Xingxing Diao; Ariane Wohlfarth; Shaokun Pang; Karl B. Scheidweiler; Marilyn A. Huestis (October 2015). "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. doi:10.1373/clinchem.2015.243535. PMID 26430074.

[2] Shevyrin, Vadim; Melkozerov, Vladimir; Nevero, Alexander; Eltsov, Oleg; Morzherin, Yuri; Shafran, Yuri (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] Nahoko Uchiyama; Yoshihiko Shimokawa; Maiko Kawamura; Ruri Kikura-Hanajiri; Takashi Hakamatsuka (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.

[4] Xingxing Diao; Karl B. Scheidweiler; Ariane Wohlfarth; Mingshe Zhu; Shaokun Pang; Marilyn A. Huestis (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: 256–267. doi:10.1007/s11419-016-0312-2.

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

[6] Hess, Cornelius; Schoeder, ClaraT.; Pillaiyar, Thanigaimalai; Madea, Burkhard; Müller, ChristaE. (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. ISSN 1860-8965. PMC 4929166. PMID 27429655.

[7] Jordan Trecki; Roy R. Gerona; Michael D. Schwartz (July 2015). "Synthetic Cannabinoid–Related Illnesses and Deaths". 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). {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)

[9] Drug Enforcement Administration, Department of Justice (2015). "Schedules of controlled substances: Temporary placement of three synthetic cannabinoids into schedule I. Final order". Federal register. 80 (20): 5042–7. 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