5F-PB-22

5F-PB-22
Legal status
Legal status
Identifiers
  • 1-fluoropentyl-1H-indole-3-carboxylic acid 8-quinolinyl ester
CAS Number
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H21FN2O2
Molar mass376.431 g·mol−1
3D model (JSmol)
  • C1=CC=C2C(=C1)C(=CN2CCCCCF)C(=O)OC3=CC=CC4=C3N=CC=C4
  • InChI=1S/C23H21FN2O2/c24-13-4-1-5-15-26-16-19(18-10-2-3-11-20(18)26)23(27)28-21-12-6-8-17-9-7-14-25-22(17)21/h2-3,6-12,14,16H,1,4-5,13,15H2
  • Key:MBOCMBFDYVSGLJ-UHFFFAOYSA-N

5F-PB-22 (5F-QUPIC or Quinolin-8-yl 1-fluoroPentyl-1H-Indole-3-8-Carboxylate) is a designer drug which acts as a cannabinoid agonist. The structure of 5F-PB-22 appears to have been designed with an understanding of structure–activity relationships within the indole class of cannabinoids.

The indazole analogue 5F-NPB-22 (5F-QUPINAC) is known.

Pharmacology

5F-PB-22 acts as a full agonist with a binding affinity of 0.468 nM at CB1 and 0.633 nM at CB2 cannabinoid receptors.

As of October 2015 5F-PB-22 is a controlled substance in China.

In January 2014, 5F-PB-22 was designated as a Schedule I controlled substance in the United States after several deaths were associated with its use.

In the United Kingdom, 5F-PB-22 is now classified and controlled as a Class B drug, following the November 2016 amendment to the Misuse of Drugs Act 1971. Several other synthetic cannabinoids structurally related to JWH-018, like 5F-PB-22, were also classified in this amendment.

See also

References

  1. ↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ↑ Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, et al. (August 2015). "Effects of bioisosteric fluorine in synthetic cannabinoid designer drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135". ACS Chemical Neuroscience. 6 (8): 1445–58. doi:10.1021/acschemneuro.5b00107. PMID 25921407.
  3. ↑ "5F-PB-22". Forendex. Archived from the original on 27 September 2015. Retrieved 24 June 2015.
  4. ↑ "5-fluoro NPB-22 (CAS 1445579-79-2)". www.caymanchem.com. Retrieved 2026-06-26.
  5. ↑ 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.
  6. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  7. ↑ Behonick G, Shanks KG, Firchau DJ, Mathur G, Lynch CF, Nashelsky M, et al. (October 2014). "Four postmortem case reports with quantitative detection of the synthetic cannabinoid, 5F-PB-22". Journal of Analytical Toxicology. 38 (8): 559–62. doi:10.1093/jat/bku048. PMC 4334789. PMID 24876364.
  8. ↑ 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.
  9. ↑ "The Misuse of Drugs Act 1971 (Amendment) Order 2016". www.legislation.gov.uk. Retrieved 2017-12-20.