THJ-2201

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]

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

It is a structural analog of AM-2201 in which the central indole ring has been replaced by indazole.[5]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. 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): 157–69. 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. 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. 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): 103–7. 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 requires |journal= (help)CS1 maint: multiple names: authors list (link)
9. "Schedules of controlled substances: temporary placement of three synthetic cannabinoids into schedule I. Final order". Federal Register. 80 (20): 5042–7. January 2015. 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.