Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

5F-APINACA

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused with5F-AB-PINACA.

Pharmaceutical compound
5F-APINACA
Clinical data
Other names5F-AKB-48, 5F-AKB48
Legal status
Legal status
Identifiers
  • N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H30FN3O
Molar mass383.511 g·mol−1
3D model (JSmol)
  • O=C(NC1(C[C@@H]2C3)C[C@H](C2)C[C@H]3C1)C4=NN(CCCCCF)C5=CC=CC=C54
  • InChI=1S/C23H30FN3O/c24-8-4-1-5-9-27-20-7-3-2-6-19(20)21(26-27)22(28)25-23-13-16-10-17(14-23)12-18(11-16)15-23/h2-3,6-7,16-18H,1,4-5,8-15H2,(H,25,28)/t16-,17+,18-,23?
  • Key:UCMFSGVIEPXYIV-XHICYHHKSA-N

5F-APINACA (also known asA-5F-PINACA,[3]5F-AKB-48 or5F-AKB48) is anindazole-basedsynthetic cannabinoid that has been sold online as adesigner drug.[4][5] Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with a 5-fluoropentyl chain on the indazole 1-position, and 5F-APINACA falls within the claims of this patent, as despite not being disclosed as an example, it is very similar to the correspondingpentanenitrile and 4-chlorobutyl compounds which are claimed as examples 3 and 4.[6]

5F-APINACA was first identified in South Korea.[7] It is expected to be a potentagonist of theCB1 receptor andCB2 receptor.[8] Its metabolism has been described in literature.[9][10][11][12]

Pharmacology

[edit]

5F-APINACA acts as afull agonist with abinding affinity of 1.94 nM atCB1 and 0.266 nM atCB2cannabinoid receptors.[13]

Legality

[edit]

In the United States, 5F-APINACA is aSchedule I controlled substance.[14]

5F-APINACA is anAnlage II controlled drug in Germany since July 2013.

As of October 2015, 5F-APINACA is a controlled substance in China.[15]

5F-APINACA is banned in the Czech Republic.[16]

See also

[edit]

References

[edit]
  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. ^"Substance Details 5F-APINACA". Retrieved2024-01-22.
  3. ^Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids".Drug Testing and Analysis.15 (3):255–276.doi:10.1002/dta.3403.PMID 36346325.
  4. ^"AKB48N-(5-fluoropentyl) analog". Cayman Chemical. Retrieved6 July 2015.
  5. ^"5F-AKB48"(PDF). Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG). 18 February 2013. Retrieved6 July 2015.
  6. ^WO 2003/035005
  7. ^Chung H, Choi H, Heo S, Kim E, Lee J (January 2014). "Synthetic cannabinoids abused in South Korea: drug identifications by the National Forensic Service from 2009 to June 2013".Forensic Toxicology.32 (1):82–88.doi:10.1007/s11419-013-0213-6.S2CID 23058813.
  8. ^"AKB48 (APINACA) and 5F-AKB48 (5F-APINACA)"(PDF). Drug Enforcement Administration. May 2013. Retrieved6 July 2015.
  9. ^Jang M, Shin I, Kim J, Yang W (February 2015). "Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry".Forensic Toxicology.33 (2):221–234.doi:10.1007/s11419-015-0265-x.S2CID 3038555.
  10. ^Karinen R, Tuv SS, Øiestad EL, Vindenes V (January 2015). "Concentrations of APINACA, 5F-APINACA, UR-144 and its degradant product in blood samples from six impaired drivers compared to previous reported concentrations of other synthetic cannabinoids".Forensic Science International.246:98–103.doi:10.1016/j.forsciint.2014.11.012.PMID 25485949.
  11. ^Holm NB, Pedersen AJ, Dalsgaard PW, Linnet K (March 2015). "Metabolites of 5F-AKB-48, a synthetic cannabinoid receptor agonist, identified in human urine and liver microsomal preparations using liquid chromatography high-resolution mass spectrometry".Drug Testing and Analysis.7 (3):199–206.doi:10.1002/dta.1663.PMID 24802286.
  12. ^Wohlfarth A, Castaneto MS, Zhu M, Pang S, Scheidweiler KB, Kronstrand R, et al. (May 2015)."Pentylindole/Pentylindazole Synthetic Cannabinoids and Their 5-Fluoro Analogs Produce Different Primary Metabolites: Metabolite Profiling for AB-PINACA and 5F-AB-PINACA".The AAPS Journal.17 (3):660–677.doi:10.1208/s12248-015-9721-0.PMC 4406957.PMID 25721194.
  13. ^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.
  14. ^"Schedules of Controlled Substances: Temporary Placement of Six Synthetic Cannabinoids (5F-ADB, 5F-AMB, 5F-APINACA, ADB-FUBINACA, MDMB-CHMICA and MDMB-FUBINACA) Into Schedule I".Drug Enforcement Administration. Archived fromthe original on 2019-10-17. Retrieved2017-03-17.
  15. ^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on the issuance of the "Regulations on the Listing of Non-Medicinal Narcotic Drugs and Psychotropic Drugs"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
  16. ^"Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)"(PDF) (in Czech). Ministerstvo zdravotnictví. Archived fromthe original(PDF) on 2016-03-09. Retrieved2016-02-06.

External links

[edit]
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-3-tetrahydrocannabinols
Delta-4-tetrahydrocannabinols
Delta-7-tetrahydrocannabinols
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Delta-11-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers

(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
Retrieved from "https://en.wikipedia.org/w/index.php?title=5F-APINACA&oldid=1294239102"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp