5F-PB-22

5F-PB-22 (5F-QUPIC or quinolin-8-yl 1-pentyfluoro-1H-indole-3-8-carboxylate) is a designer drug which acts as a cannabinoid agonist.[1] The structure of 5F-PB-22 appears to have been designed with an understanding of structure–activity relationships within the indole class of cannabinoids.[2]

5F-PB-22
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-Pentyfluoro-1H-indole-3-carboxylic acid 8-quinolinyl ester
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H21FN2O2
Molar mass376.431 g·mol−1
3D model (JSmol)
SMILES
  • C1=CC=C2C(=C1)C(=CN2CCCCCF)C(=O)OC3=CC=CC4=C3N=CC=C4
InChI
  • 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

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.[3]

As of October 2015 5F-PB-22 is a controlled substance in China.[4]

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.[5][6]

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.[7]

See also

References
  1. 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.
  2. "5F-PB-22". Forendex. Archived from the original on 27 September 2015. Retrieved 24 June 2015.
  3. 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.
  4. "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.
  5. 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.
  6. 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.
  7. "The Misuse of Drugs Act 1971 (Amendment) Order 2016". www.legislation.gov.uk. Retrieved 2017-12-20.
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