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5F-PB-22

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
5F-PB-22
Legal status
Legal status
Identifiers
  • 1-Pentyfluoro-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 orquinolin-8-yl 1-pentyfluoro-1H-indole-3-8-carboxylate) is adesigner drug which acts as acannabinoid agonist.[2] The structure of 5F-PB-22 appears to have been designed with an understanding ofstructure–activity relationships within the indole class of cannabinoids.[3]

Pharmacology

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5F-PB-22 acts as afull agonist with abinding affinity of 0.468 nM atCB1 and 0.633 nM atCB2cannabinoid receptors.[4]

Legal status

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

In January 2014, 5F-PB-22 was designated as aSchedule I controlled substance in the United States after several deaths were associated with its use.[6][7]

In the United Kingdom, 5F-PB-22 is now classified and controlled as aClass B drug, following the November 2016 amendment to theMisuse of Drugs Act 1971. Several other synthetic cannabinoids structurally related toJWH-018, like 5F-PB-22, were also classified in this amendment.[8]

See also

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References

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  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. Retrieved2023-08-27.
  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 fromthe original on 27 September 2015. Retrieved24 June 2015.
  4. ^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.
  5. ^"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 fromthe original on 1 October 2015. Retrieved1 October 2015.
  6. ^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.
  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. ^"The Misuse of Drugs Act 1971 (Amendment) Order 2016".www.legislation.gov.uk. Retrieved2017-12-20.
Phytocannabinoids
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Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
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agonists /
neocannabinoids
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(dibenzopyrans)
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Adamantoylindoles
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Others
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers

(inactivation inhibitors)
Anticannabinoids
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