THJ-2201

THJ-2201

Legal status
Legal status	CA: Schedule II DE: Anlage II (Prohibited) US: Schedule I
Identifiers
IUPAC name [1-(5-Fluoropentyl)-1H-indazol-3-yl](1-naphthyl)methanone
CAS Number	972102-31-2
PubChem (CID)	91864533
ChemSpider	30646749
Chemical and physical data
Formula	C23H21FN2O
Molar mass	360.42 g/mol
3D model (Jmol)	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It is a structural analog of AM-2201 in which the central indole ring has been replaced by indazole.^[5]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]

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

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. 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).
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.